Staypineapple, An Iconic Hotel, The Loop

4-star hotel Excellent 1 W Washington St, Chicago, IL, 60601
Staypineapple, An Iconic Hotel, The Loop

About Staypineapple, An Iconic Hotel, The Loop

Historic Chicago architecture, designed by world renowned architect Daniel Burnham, with mosaic floors and marble ceilings inspire luxury at this hotel in Chicago’s Loop. Shopping on famed Michigan Avenue and Millennium Park are a short walk away. White and gray colors with mahogany furnishings are balanced by modern amenities like a flat-screen TV and plush bedding in each room. Select suites feature stunning views of Millennium Park and Lake Michigan. Staypineapple, An Iconic Hotel, The Loop has a fitness center and bicycle rental service. Pets receive free bedding and water upon request. Chicago’s entertainment center, Navy Pier, is 1.9 mi from the hotel. The Chicago Theater and Art Institute of Chicago are less than 5 minutes’ walk away.

Amenities

  • On-site parking
  • 24-hour front desk
  • Meeting space
  • Fitness center
  • On-site dining
  • Valet parking
  • Bar / lounge
  • Café / coffee shop
  • Business center
  • Express check-in / check-out
  • Concierge
  • Dry cleaning
  • Self-service laundry
  • Luggage storage
  • Multilingual staff
  • Full kitchen / kitchenette
  • In-room refrigerator
  • Spa / sauna
  • Pet friendly
  • Public transit access
  • Smoke-free property
  • Air conditioning
  • Elevator
  • In-room safe

Reviews

4.5 / 5
Excellent 1508 reviews

The hotel is generally well-liked for its location, comfortable beds, and friendly staff. However, some guests have expressed dissatisfaction with the cleanliness of the rooms, the size of the bathrooms, and the lack of daily housekeeping.

What guests liked
  • Convenient location
  • Comfortable beds
What could be better
  • Inconsistent cleanliness
  • Small bathrooms
  • Sharon Jun 2026 · via expedia
    4/5

    We loved character of the building and the proximity to downtown. However the hotel was not as secure as others. Anyone from the public could access elevators. Also a $25 amenities fee was attached for cookies, water, and bikes. We did not need or use any of these.

  • Steven Jun 2026 · via hotels.com
    5/5

    I'm officially a Staypineapple fan! Great branding. Attentive, capable staff, cool vibe. Awesome location.

  • John Jun 2026 · via hotels.com
    3/5

    Room was clean, and comfortable although quite small. Valet parking was terrible despite being costly, the “free” amenities have a value of perhaps 5 dollars but the “amenity” fee is $25.00. Taxes, non-optional fees, parking costs, etc can easily make the final costs more than 150 per cent of the advertised price for a night’s stay, and lack of a doorman, any bellmen, at most two front desk people, and one valet make this a hotel that has nice rooms and no service and much personal inconvenience. Being hip and cute is not good enough.

  • Dorothy Jun 2026 · via hotels.com
    5/5

    Stylish architecture and details of historic building. Convenient to subway stations.

  • Jessica Jun 2026 · via expedia
    5/5

    Darnell at the front desk was so warm and helpful. Our room was as pretty and cozy as it gets, the view to die for. The restaurant downstairs has the best French toast on earth. For reals!

  • Wren Jun 2026 · via hotels.com
    4/5

    Greta location, beautiful building and rooms (high ceilings, huge windows), and a great restaurant downstairs (under different ownership). We stayed here last two years ago and it feels not as well managed as it was then. In room furniture/sofa was very stained, curtain was hanging off the hooks, lots of paint dents, staff less engaged etc. I wish they were doing a better job of maintaining this beautiful property. We may be back due to the strong points, but I will search other options as well in future.

  • Marlena Jun 2026 · via expedia
    5/5

    Great spot in the city with convenient valet parking. Big, clean rooms with tall ceilings. Comfy beds and great water pressure. Would definitely stay again. Dog and baby friendly

  • Philip Jun 2026 · via expedia
    4/5

    Good location, friendly staff

  • Roxane Jun 2026 · via booking
    4.5/5

    Superb

  • Diana Jun 2026 · via hotels.com
    5/5

    Such a fun hotel! Great location, classy interior, and eco-friendly water. This would also be the best choice if you’re traveling with a dog.

  • Julie Jun 2026 · via booking
    5/5

    Happy

  • Lisa Jun 2026 · via booking
    4.5/5

    Superb

  • Melanie Jun 2026 · via hotels.com
    3/5

    Mixed stay with lacking housekeeping but decent room. Resort fee is ludicrous for what you get.

  • Lynn Jun 2026 · via expedia
    3/5

    A few things could be improved. Our check-in experience was a bit awkward as the host assigned the smallest room to the couple rather than the solo traveler, which felt like an oversight. The lobby seating is showing wear, and the in-room bedding instructions were more confusing than they needed to be. At $500+ per night, we expected more. Housekeeping is every other day, which felt inadequate at this price. The mandatory amenity fee is also frustrating, not because it's unexpected, but because it's hard to justify keeping it separate from the room rate.

  • Myung Jun 2026 · via expedia
    5/5

    All aspects have met to my satisfaction, I would definitely come back when I go to Chicago. Thank you.

  • Connor Jun 2026 · via booking
    4/5

    Very good

  • Pauline Jun 2026 · via booking
    5/5

    Cozy, comfortable, the beds were super comfortable Bathrooms could use an upgrade

  • Kerry May 2026 · via expedia
    5/5

    It was great

  • Brian May 2026 · via expedia
    5/5

    Best hotel in Chicago!

  • Debby May 2026 · via expedia
    5/5

    Such a lovely hotel with a beautiful, excellent staff, and lots of character!

  • Brianna May 2026 · via booking
    5/5

    Exceptional

  • kelly May 2026 · via expedia
    4/5

    The property has a lot of character and it is centrally located. We really enjoyed being able just to walk outside of our door and have access to so many great things in downtown Chicago. The room was very small and the bedding was extremely comfortable. One thing to note, after paying the premium price some of the amenities included water bottles in our room and coffee and Wi-Fi. But upon checking out, it was actually $25 per day to have one water bottle and coffee in our room. It’s not really an amenity if you pay for it. Just wish that was upfront instead of an added cost of $50 to our weekend you don’t have an option for those amenities, but they should be already included in the price. The restaurant that just opened was not great as well. I don’t think it is affiliated with a hotel but it’s in the lobby of the hotel and we had breakfast and it was about a five out of 10. The staff were incredibly helpful and welcoming.

  • yijing May 2026 · via expedia
    5/5

    Good

  • Jeremy May 2026 · via expedia
    5/5

    The staff is super friendly and easy to talk to so you don’t have to worry about much! The location is amazing if you wanna explore downtown Chicago!

  • Lyz May 2026 · via booking
    4.5/5

    Superb

  • Yolanda May 2026 · via expedia
    5/5

    It was a great stay. Staff were helpful. Wish the restaurant was open during our stay.

  • Elaine May 2026 · via expedia
    5/5

    Lovely view from the room. Very Chicago

  • Teah May 2026 · via hotels.com
    5/5

    Great experience! The pineapple shortbread cookies sealed the deal for me!

  • Michelle May 2026 · via booking
    4/5

    They use old fashioned keys, so the elevators to guest rooms are unsecured.

  • Michelle May 2026 · via priceline
    4/5

    They use old fashioned keys, so the elevators to guest rooms are unsecured.

  • cary May 2026 · via hotels.com
    5/5

    a great stay in the loop, a convenient location to all the sights and sounds of Chicago

  • Heather May 2026 · via booking
    5/5

    The staff was super friendly No parking

  • Josefina May 2026 · via priceline
    4.5/5

    Clean and helpful staff Na

  • Josefina May 2026 · via booking
    4.5/5

    Clean and helpful staff Na

  • Heather May 2026 · via priceline
    5/5

    No parking

  • Sharon May 2026 · via hotels.com
    4/5

    Enjoyably quirky hotel--pineapple theme, free water (still, sparkling, or hot) in the lobby, European-style comforter, actual keys (not a key card), one-of-a-kind in-room coffee maker. Good location for bargain shopping (Nordstrom Rack, Uniqlo, Primark); easy walk to Art Institute. The newly-opened restaurant in the lobby has a menu that strains the conception of fusion past its breaking point and the service is a work-in-progress. Not too many other food options in the immediate area.

  • Brenda May 2026 · via expedia
    5/5

    Clean rooms, comfy bed.

  • Cynthia May 2026 · via hotels.com
    5/5

    The staff was beyond amazing! They were cheerful and incredibly helpful. They were patient with questions and requests and truly seemed to enjoy their jobs! The room had so much charm and very helpful amenities (robes, iron, extra blankets, a free water bottle, free coffee, fridge, blow dryer, etc.). I don’t believe all the rooms have a great view but ours had a fantastic view of N. State St., with a perfect view of the Chicago Theatre, and a great view down Washington Street right to Lake Michigan!! It was so nice to be able to sit with a coffee in the morning, enjoying the beautiful views! I highly recommend this fantastic hotel and will definitely be going back!

  • Kari May 2026 · via hotels.com
    5/5

    Our room was spotless, staff was helpful, and our bed was so comfortable.

  • Beth May 2026 · via expedia
    5/5

    Easy access to many points of interests and shopping

  • Spencer May 2026 · via expedia
    5/5

    Traveled with my wife, used the bikes to cruise along the water. Great time!

  • Susanne May 2026 · via expedia
    5/5

    The hotel was super cool with original architecture.

  • Deborah May 2026 · via hotels.com
    5/5

    Funky hotel. Great location. Good vibe.

  • Robin May 2026 · via priceline
    5/5

    I loved the view. The gentleman that checked us in was very nice. The room was quiet. We really liked how well the hotel had been maintained over the years. No complaints the hotel was beautiful.

  • Tajia May 2026 · via booking
    5/5

    Exceptional

  • Robin May 2026 · via booking
    5/5

    I loved the view. The gentleman that checked us in was very nice. The room was quiet. We really liked how well the hotel had been maintained over the years. No complaints the hotel was beautiful.

  • Yebandz May 2026 · via priceline
    2/5

    It was clean. Some staffs.

  • Yebandz May 2026 · via booking
    2/5

    It was clean. Some staffs.

  • Jacqueline May 2026 · via hotels.com
    5/5

    This is my favorite hotel ever! I love that the integrity of Daniel Burnham's elements hae not been tampered with, which adds to the overall charm of the place. The staff--particularly Sashon(?) were extremely helpful in helping me get transport to Navy Pier. I love the new restaurant, where I had breakfast-perhaps the best toast ever! The entire staff is welcoming, helpful, and convey a high degree of hospitality. It is located close to the CTA--a big plus when coming from O'Hare. I frequently travel alone, so the high degree of safety at this hotel is always a comfort.

  • Gretchen May 2026 · via priceline
    4.5/5

    Unique and historic

  • Gretchen May 2026 · via booking
    4.5/5

    Unique and historic

  • Kira May 2026 · via booking
    3.5/5

    The bed was comfortable! Location is good. Liked the old hotel. The amenities fee of $25.00 a day is ridiculous. For that reason alone I wouldn't stay again at this hotel!

  • Kira May 2026 · via priceline
    3.5/5

    The amenities fee of $25.00 a day is ridiculous. For that reason alone I wouldn't stay again at this hotel!

  • Scott May 2026 · via hotels.com
    5/5

    Great location in the heart of the loop. Super friendly and attentive staff. An older building, but clean and well-maintained. Would definitely stay here again.

  • Geraldine May 2026 · via booking
    4.5/5

    Superb

  • Carol May 2026 · via expedia
    5/5

    yes.

  • Damien May 2026 · via booking
    3.5/5

    Liked the location and friendliness of staff. By "iconic" they mean historical building but a little rundown. Don't get me wrong the elevator has some vintage charm but the rooms and the bathrooms have known better days

  • Devon May 2026 · via expedia
    2/5

    Good location but terrible experience. There was one staff member who was kind and helpful when we checked out but the other two I encountered were really unpleasant. I usually don’t have a car in cities but I needed one this trip due to my work conference being outside the city with no easy transportation to and from. The valet situation was a nightmare! One of the morning I called for my car and no one answered. I walked down to the front desk and the gentleman actually rolled his eyes and huffed at me after I asked for my car to be retrieved. It took 20 minutes and I was late for my conference. The next day I woke up extra early and called a half an hour early to accommodate for the time it takes to get the car and it ended up taking 35 minutes. I was in tears and again late for my conference. Overall not a good experience and would not recommend. The place is outdated and the pillows are not comfortable.

  • Eva May 2026 · via expedia
    5/5

    The staff were fantastic, and the beds were insanely comfortable/blankets were soft and plush. The location is advantageous- lots of shopping, food, and things to do nearby. Getting an Uber from this location was a breeze and took less than five minutes. The Valet service for Staypineapple was also good. Would definitely recommend!

  • Jessica Apr 2026 · via hotels.com
    5/5

    Clean, friendly and perfectly located.

  • Lucille Apr 2026 · via priceline
    5/5

    Location. Close to every thing. Dining,theater,sights Knowing the restaurant was being renovated at time of booking.

  • Carolina Apr 2026 · via booking
    5/5

    one of the best hotels I’ve been! all the staff were super kind, the room and the view was amazing and super comfortable

  • Lucille Apr 2026 · via booking
    5/5

    Location. Close to every thing. Dining,theater,sights Knowing the restaurant was being renovated at time of booking.

  • Amy Apr 2026 · via hotels.com
    4/5

    This is a well-located hotel with an unbeatable front desk staff. We were warned that the room would be cleaned only every other day of our 4 night stay; however, it was never cleaned or straightened up. The room also needs more light. A standing lamp behind the chair would have helped immensely. That said, when I complained about the cleaning, the absolutely wonderful front desk staff immediately both apologized and adjusted our bill. I would stay there again but...

  • Gilmar Apr 2026 · via booking
    5/5

    Exceptional

  • Bradley Apr 2026 · via expedia
    5/5

    Amazing spot, centrally located, great views

  • Justin Apr 2026 · via expedia
    4/5

    Nice building, perfect location

  • Lucy Apr 2026 · via expedia
    4/5

    Comfortable bed with everything you need. Rooms are well soundproofed. The building has nice original features.

  • Daniel Apr 2026 · via expedia
    4/5

    Very Pleased

  • Anne Apr 2026 · via hotels.com
    5/5

    I don't usually write reviews-but this hotel is a little gem. Lots of unique touches that make it stand out: amazing bedding, attention to detail with towels & robes, dog friendly, with an option to buy a stuffy for pet rescues, nice staff & a cool aluminum water bottle souvenveir.

  • Michael Apr 2026 · via hotels.com
    4/5

    Overall felt it was very average and a lot of form over function. The gym is small and could have been cleaner. I laid on the floor for abs and my shirt was filthy. Rooms seem older with some Pinneapple themed updates. Chromecast did not work. Shower made a loud banging noise and did not get as hot as it should have been. It is nice they give you a drink upon entry. They also charge a $30 amenity fee at checkout.

  • Sarah Apr 2026 · via expedia
    4/5

    This property is in a great location. The staff were friendly and the room was clean. The room we were in was very small and used. The building is really cool but we were super disappointed with it being under construction with no place to hang out and have a drink. We weren’t notified of the construction until right before our stay. We would have chosen somewhere else because of this.

  • Robert Apr 2026 · via expedia
    5/5

    Wonderful restaurant, amazing food.

  • Phil Apr 2026 · via hotels.com
    5/5

    Comfortable and a really great team working therr

  • Ana Apr 2026 · via booking
    4.5/5

    Fantastic location. Nice converted wrt deco building. Staff was very helpful and nice. May I suggest that they change the bedstand where the mattress was set on? The edges were really dangerously sharp. As in you can hit your leg a few times a day since the room is not large.

  • Aromal Apr 2026 · via booking
    0.5/5

    Bad

  • ANA Apr 2026 · via priceline
    4.5/5

    Fantastic location. Nice converted wrt deco building. Staff was very helpful and nice. May I suggest that they change the bedstand where the mattress was set on? The edges were really dangerously sharp. As in you can hit your leg a few times a day since the room is not large.

  • Zachary Apr 2026 · via expedia
    4/5

    Lobby was under construction which wasn’t attractive but also not disruptive. Hotel was fine but not glamorous. Room was small.

  • Diane Apr 2026 · via expedia
    5/5

    Convenient location, walked everywhere. Great staff, so helpful amd accommodating.

  • Zrinka Apr 2026 · via booking
    4.5/5

    Location, rooms/beds No breakfast

  • Jason Apr 2026 · via expedia
    5/5

    Nice hotel, close to a lot of things

  • Jacqueline Apr 2026 · via priceline
    5/5

    Vintage aesthetic.. Entrance… could be a bit more captivating… curbside could use more appeal.

  • Gander Apr 2026 · via priceline
    5/5

    The lobby/bar was under construction.

  • Gander Apr 2026 · via booking
    5/5

    The lobby/bar was under construction.

  • Jacqueline Apr 2026 · via booking
    5/5

    Vintage aesthetic.. Entrance… could be a bit more captivating… curbside could use more appeal.

  • Paula Apr 2026 · via hotels.com
    5/5

    Great location in downtown Chicago near good restaurants, performing arts venues, the lake, etc. Friendly and helpful staff. Cosy and comfortable rooms. Quiet at night so great for sleeping.

  • Cristina Apr 2026 · via expedia
    5/5

    Darnell was the absolute BEST!!

  • Kelly Apr 2026 · via booking
    3.5/5

    Good

  • Silvana Apr 2026 · via hotels.com
    5/5

    Yes good

  • Lisa Apr 2026 · via hotels.com
    5/5

    Great location with excellent beds

  • Creed Apr 2026 · via hotels.com
    5/5

    super friendly staff. super nice place. i’ll definitely be back.

  • Bridget Apr 2026 · via hotels.com
    5/5

    Lovely. Great staff

  • Tammy Apr 2026 · via expedia
    5/5

    Wonderful hotel. Great location at a great price.

  • Anne Mar 2026 · via expedia
    4/5

    It would have been great to know that the restaurant was closed. Thet did not notify us until the day of arrival.

  • Phil Mar 2026 · via hotels.com
    5/5

    Amazing team, super comfortable. Brilliant location. Excited to return.

  • Mary Mar 2026 · via hotels.com
    5/5

    Great location by the theatre district. The staff goes out of their way to assure a pleasant stay. We did miss the restaurant, and hope it will be back soon.

  • Julie Mar 2026 · via expedia
    5/5

    Great property, so many cute details in this historic hotel. The staff was friendly, the property was pristine, and it’s close to so many things to visit and do in Chicago. A close walk to Millennium Park, and many shops.

  • Brook Mar 2026 · via hotels.com
    4/5

    The staff were welcoming and professional! Neftali checked me in and he could not be more helpful. I loved the beds and bedding - a unique approach and the most important part of the room. The hotel decor was very near in the common areas. While the rugs and shower and a few other things were a bit dated, everything was clean and worked fine. I thought it went along with the charm of the hotel. I appreciated the small touches (reusable water bottle and water dispenser in the lobby. I’ll be back!

  • Sarah Mar 2026 · via hotels.com
    5/5

    the beds are so comfy. staff unbelievably helpful and friendly. excellent location for the weekend.10/10 would highly recommend.

  • Ezequiel Mar 2026 · via expedia
    1/5

    There was a race scheduled for Sunday morning and it make valet check out impossible, the hotel staff (Sashon) didn’t notify us during check in. And Sunday he was very condescending and rude during the checkout. When asked why weren’t directly informed about the race inconveniences, He pointed to two signs he had posted at the end of the checkout counter and he never mentioned the signs during check in. There was a customer there who missed a funeral because he failed to prepare them for the delay. If that was us I think I would seek legal action. Sashon and the pineapple staff are everything that is wrong with customer service. No accountability, no apologies for the inconvenience, no looking after the customer. I have stayed in at the pineapple 5 times and I will never stay again because of this experience

  • Brian Mar 2026 · via hotels.com
    5/5

    Amazing hotel and view!

  • mark Mar 2026 · via expedia
    5/5

    Great looking iconic property.

  • Martha Mar 2026 · via hotels.com
    4/5

    Under construction but altogether nicer downtown hotel! Very hard to distinguish outside and get to.

  • Hosam Mar 2026 · via hotels.com
    2/5

    Bed sheets weren’t smelling fresh

  • DEBBY Mar 2026 · via expedia
    4/5

    The staff and (Mr.Brown ) were extremely accommodating! It was my bday and they decorated our room with all sorts of goodies including a hand made stuffed wash cloth doggie! Our housekeeper was amazing too! The room decor is such fun and extremely clean! The only drawback is the rooms are very small and some not configured well! All and all it’s a wonderful place to experience!!!!🍍

  • Bernard Mar 2026 · via priceline
    5/5

    very good

  • Susannah Mar 2026 · via hotels.com
    5/5

    The staff was fantastic! Very friendly and helpful, and welcoming. I appreciated their help, especially when I found out I had to extend my stay in Chicago due to yet another flight being rescheduled. Your team helped my bypass the check-in process so I could keep my room. This saved me a ton of time and hassle since I had to keep working remote during my stay. Thank you!

  • Carla Mar 2026 · via priceline
    5/5

    Old carpet cleaner in room. Outdated bathroom.

  • Marsha Mar 2026 · via expedia
    4/5

    Very nice stay, room was good, enjoyed the vintage style building. Was close to everything. My only complaint was the $29 charge for amenities that was not explained at check in or anywhere else when booked. That charge should be in the initial price.

  • Kristen Mar 2026 · via expedia
    5/5

    Exceptional hotel perfectly located. Theaters and museums within blocks as well as the iconic Bean and Lakeshore Trail. The hotel has historic charm with pineapple touches that make you smile. The guest services is exceptional. They made my birthday extra special. I appreciate the free coffee every morning. Cannot beat the 12:00 checkout and it's pet friendly.

  • Analicia Mar 2026 · via expedia
    4/5

    Lots of places to eat and shop nearby

  • John Mar 2026 · via priceline
    4.5/5

    Old world style Bathtub

  • Jennifer Mar 2026 · via expedia
    5/5

    Nice clean room with tons of historic charm. Love the duvets and view to Millennium Park

  • URSULA Mar 2026 · via priceline
    5/5

    Beds are amazingly comfortable

  • Joseph Mar 2026 · via hotels.com
    5/5

    Close to shops, theater and restaurants.

  • Philip Mar 2026 · via expedia
    5/5

    Center of the Loop, easy walk to a majority of landmark sights.

  • Cassandra Mar 2026 · via hotels.com
    5/5

    Our stay was fantastic, centrally located to the waterfront park, food, shopping and LLine. It only coat $2.50 to come in from OHare. The hotel was beautiful, stylish and clean. Just loved it.

  • Samantha Mar 2026 · via hotels.com
    5/5

    The staff was amazing and even sent a bottle of wine with a hand written card! The room was clean and comfortable and I was happy with how close everything was!

  • Danielle Mar 2026 · via priceline
    5/5

    Everything/everyone was very welcoming. The location was beyond perfect!! Not one thing!

  • Peggy Feb 2026 · via expedia
    3/5

    Everything was nice and clean. The incidentals charge wzs $58 for bottled water and cellophane wrapped cookies. That was a surprise at the end of stay.

  • Jolyn Feb 2026 · via hotels.com
    5/5

    Everything was great, including the staff

  • Louise Feb 2026 · via priceline
    4.5/5

    Perfect location and Burnham’s building is stunning. The bed and the comforter were extremely comfy. More food and drink options would be better

  • Francisco Feb 2026 · via expedia
    5/5

    Customer service

  • Megan Feb 2026 · via hotels.com
    5/5

    Such a fantastic location with friendly staff and wonderful amenities.

  • Alan Feb 2026 · via expedia
    5/5

    Clean Room. Easy and quick check in. The staff is always super helpful. The amenities are a nice plus. Rooms are quiet (no other room noises) and the beds are super comfy!

  • Aimee Feb 2026 · via expedia
    3/5

    This hotel has a lot of good things but also some bad. It’s loud. All the time. Sirens, trains, etc. My room had a ripped blanket. I couldn’t use the hot water because if I turned it on something was wrong with the pipe creating a loud noise. Hotel was booked so no fixing this. Staff is kind. They will overcharge you though. They kept adding extra stuff to the bill. I paid taxes through Expedia and then they made me pay taxes again. So even though they waived the amenities fee I still paid an extra $47.00 after what Expedia charged for taxes. So just be aware what Expedia says is your final price is not. There is a $29.29 nightly amenities fee per room on top of extra taxes.

  • Juarez Feb 2026 · via priceline
    4.5/5

    Only few things I could really complain about would be that when we first went to drop off our bags at the hotel the staff member said he would call us to let us know that our room was ready, but they in fact did not. Another thing would be that the TVs aren't simple to use in the case that it doesn't show you the menu of the channels so you just have to scroll until you find a channel you actually would like to watch.

  • Linda Feb 2026 · via priceline
    4.5/5

    Our room was quiet! Bed and pillows were very compfy!! Staff was pleasant and efficient. Interior was unique and interesting historically. Fantastic location and our room had a great view of State Street and Millennium Park. Overall clean environment. Room was equipped with everything we needed! The refillable water bottle and water station was a nice touch and way more convenient than hauling multiple water bottle to our room. (A cost savings too) There were some obvious signs of wear at the property. We realized going in that it is an old building (part of the charm actually!), but some minor upkeep issues were noticeable. Some chips out of the woodwork, closet doors etc. Bathtub was pretty old and a little beat up. Mattress encasement was ripped. Also, disappointed that the restaurant was closed. Not informed until morning of check in.

  • Trimont Feb 2026 · via expedia
    5/5

    The room was

  • Mona Feb 2026 · via priceline
    5/5

    The location, vintage interior, real room keys, super affordable The restaurant was down during our stay, most likely under remodeling.

  • Jonas Feb 2026 · via expedia
    5/5

    The room was clean, the staff at check in was great. The lobby amenities were good. Having a water refill station with still and sparkling water was clutch. Location is amazing! Will return.

  • Lucas Feb 2026 · via expedia
    5/5

    The European duvets were amazing! It made our sleep so

  • Amanda Feb 2026 · via expedia
    5/5

    We loved how this historic building has been maintained and its classic style carried through to the room furnishings. We also loved having 2 duvets on the bed! Such a thoughtful touch. Also appreciated the attention to environmental responsability.

  • Irasema Feb 2026 · via expedia
    5/5

    Great location

  • John Feb 2026 · via expedia
    4/5

    Will definitely be back.

  • Barbara Feb 2026 · via hotels.com
    5/5

    Amazing hotel and amazing staff.

  • Timothy Feb 2026 · via hotels.com
    5/5

    The whole ambience of the hotel, room was very clean, staff was very friendly.

  • kawe Feb 2026 · via priceline
    5/5

    This is our go-to hotel for stays in the city.

  • Peter Feb 2026 · via hotels.com
    2/5

    Restaurant is closed for renovation. No food in the building. Dirty carpet, no four star amenities, indifferent, unprofessional staff.

  • Robin Feb 2026 · via hotels.com
    5/5

    Very friendly and attentive staff. The bedding is super comfortable.

  • Michael Feb 2026 · via expedia
    5/5

    Staff was excellent and the building is literally iconic. Our only negative is that the bathrooms were a bit tired. Ours had a yellowed, loose fitting toilet seat and a light out on the mirror.

  • Danielle Feb 2026 · via hotels.com
    5/5

    Beds were super comfy

  • Jane Feb 2026 · via hotels.com
    5/5

    Enjoyed our stay. Bummed that the bar/restaurant was closed for renovations though. Otherwise, the hotel was in a great location, clean rooms, comfy beds, overall good experience!

  • Raymond Feb 2026 · via expedia
    3/5

    I was not informed in advance that the restaurant/bar was closed for renovations. I would have stayed at a different hotel had I known.

  • James Feb 2026 · via hotels.com
    5/5

    Very friendly and courteous staff. The room was beautiful and very comfortable. We had a view of the lake in millennium Park the perfect place to stay!

  • Tammara Feb 2026 · via hotels.com
    5/5

    Enthralled by the iconic building and its historic details; superb location; and the winter view was gorgeous. On this wickedly cold stay the soft, plush robes and warm duvets were perfect match with the hot chocolate from room service.

  • Aidee Jan 2026 · via expedia
    5/5

    This is my favorite hotel downtown. I book here when I can. The hotel is clean and the architecture is so beautiful. Stay is always welcoming and you get a free drink from the bar as well as cookies!

  • Evans Jan 2026 · via priceline
    5/5

    Everything! The hotel was clean, friendly located in a fantastic location. Definitely my next stay when I visit Chicago. Nothing it was perfect and so cute !!!!

  • Lauren Jan 2026 · via hotels.com
    5/5

    Hotel was great, bedding was very comfortable. I have trouble sleeping in hotels where the bed is too firm or sheets are too stiff, they did a great job with comfort.

  • Masashi Jan 2026 · via expedia
    5/5

    Clean room

  • Janice Jan 2026 · via priceline
    5/5

    Beautiful building, cool lobby and bar area, clean rooms with very cozy beds and linens. The only thing I can think of is that the decor in the halls is dark, I prefer lighter colors.

  • Stephanie Jan 2026 · via hotels.com
    5/5

    Great location, beautiful hotel, plus comfortable and clean rooms made this stay absolutely perfect

  • Jeffery Jan 2026 · via hotels.com
    4/5

    Oh yes, very nice

  • joseph Jan 2026 · via expedia
    5/5

    Clean shopping near by

  • Rebecca Jan 2026 · via hotels.com
    4/5

    Beds are very comfortable and clean. Was given a room with a great view which was very much appreciated. However, the shower had a considerable amount of black mold. Not sure why you would have wallpaper in a bathroom with no ventilation. As someone who is allergic to mold this was a bit of a bummer. The rest of the hotel seemed in tip top condition and the staff were fantastic.

  • Christiano Jan 2026 · via expedia
    5/5

    Clean room, helpful staff

  • Susan Jan 2026 · via hotels.com
    5/5

    Rooms were very comfortable. The staff was very friendly upon check in. Loved the location to everything downtown.

  • Thomas Jan 2026 · via expedia
    5/5

    Clean rooms. Quiet.

  • Annette Jan 2026 · via hotels.com
    5/5

    Restaurant was good.

  • Pauline Jan 2026 · via hotels.com
    4/5

    Clean

  • Kristin Dec 2025 · via hotels.com
    5/5

    Good location, clean, comfy bed, love the hotel robe, friendly staff, delicious cookies. Bathroom could use some updating but overall great stay.

  • MICHELE Dec 2025 · via expedia
    5/5

    Very clean and staff was very friendly.

  • Julie Dec 2025 · via hotels.com
    4/5

    We stayed one night. Beds were comfy. Plenty of hot water for showers. Bar was only open til 9 pm. Restaurant opens at 9 am. Walked to the Goddess and the Baker for breakfast before that.

  • cheryl Dec 2025 · via expedia
    5/5

    Friendly, helpful staff, great bedding, perfect location especially if you're visiting the Christkindlmarket

  • Lori Dec 2025 · via expedia
    5/5

    Location was great, staff was very friendly, and the rooms were clean.

  • David Dec 2025 · via hotels.com
    5/5

    Charming, historic hotel in absolutely ideal location, steps from Chicago Theatre, Michigan Ave and Millenium Park. Nice touches of hospitality, like free welcome drink, plate of berries and macaroons and a bottle of Prosecco.

  • Sylvia Dec 2025 · via expedia
    5/5

    Great location

  • Bernadette Dec 2025 · via expedia
    5/5

    The room and the view was amazing. Very clean the robes and towels and the beds were the most comfortable items I have ever seen. And the staff? They went above and beyond to make our stay perfect. And to find out it’s a pet friendly hotel? I most definitely will be back. All the extra amenities on top of everything? This place is a must stay hotel.

  • Juliana Dec 2025 · via hotels.com
    4/5

    Amenities the best , customer service ok

  • SUSAN Dec 2025 · via expedia
    5/5

    Stayed here when it was the Burnham and thankfully it is still a gorgeous property. Very noisy outside - street “drummers” were loud and incessant from 8am - 7pm. Missed the old wine/happy hour.

  • Beth Dec 2025 · via expedia
    5/5

    I had a perfect experience at Staypineapple. They took such good care of my toddler and me. They went above and beyond over and over again, from helping me get all our luggage into our room to leaving a stuffed animal and candy for my little one to bringing complimentary milk and cookies to us to squeezing us into the busy restaurant to checking in on us throughout our stay. The staff was exceptional, and the location was perfect for everything we wanted to do.

  • Angie Dec 2025 · via expedia
    5/5

    The room was clean, the stuff was kind, the location was was great . I would recommend Staypineapple Hotel.

  • Richard Dec 2025 · via expedia
    5/5

    Great location, clean, and very helpful and friendly staff

  • Mi Dec 2025 · via expedia
    5/5

    The mattress is comfortable. And the room has a perfect and very impressive street view. And the hotel location is convenient to reach Millennium Park and Magnificent Mile.

  • Lou Dec 2025 · via hotels.com
    5/5

    Great staff and the location was perfect.

  • Brian Dec 2025 · via expedia
    5/5

    Gem near Millennium Park.

  • Timothy Dec 2025 · via expedia
    5/5

    My go-to Chicago hotel. Love it!

  • Sandra Dec 2025 · via expedia
    5/5

    Staff were amazing

  • Anthony Dec 2025 · via hotels.com
    5/5

    Fantastic location, excellent service, great clean room w/ comfortable bed. For the price this was a great stay and would definitely go back. The restaurant/bar was pretty good too!

  • Candice Dec 2025 · via hotels.com
    5/5

    Lovely hotel, very clean, great customer service. Well located!

  • Kathleen Dec 2025 · via expedia
    5/5

    Great hotel location and friendly staff!

  • diane Dec 2025 · via hotels.com
    4/5

    Room was great! Great view! Staff was attentive and responsive.

  • Jennifer Dec 2025 · via expedia
    5/5

    Clean. Great vibe.

  • James Dec 2025 · via expedia
    5/5

    Perfect stay. Great location, lovely room with view of Marshall Fields State Street Christmas display. The people were just great.

  • Marquette Dec 2025 · via hotels.com
    5/5

    Clean, easy checkin, great staff

  • Danielle Nov 2025 · via expedia
    5/5

    Clean room and kind staff. First hotel I’ve been to that actually had a key to open the door, very cool. Would stay again.

  • Linda Nov 2025 · via hotels.com
    5/5

    We first walked in and got greeted immediately. The gentleman at the desk was very friendly and attentive, joking with my kids and making them laugh. He explained everything about the room and the hotel. Made us feel like we were at home. Thanks for such great hospitality!

  • william Nov 2025 · via expedia
    5/5

    Our room was very clean, beautiful view, and extremely friendly staff. I would especially like to thank and acknowledge the outstanding customer service from Beth Ann. Her help and kindness were greatly appreciated.

  • Steven Nov 2025 · via expedia
    4/5

    Everything was very bice

  • Douglas Nov 2025 · via hotels.com
    5/5

    Staff courteous and helpful.

  • Faith Nov 2025 · via hotels.com
    5/5

    Room was very clean, staff courteous! I love the place!

  • Kristen Nov 2025 · via hotels.com
    4/5

    Great personalized touches. A goodie bag and cookies and milk. What more could a girl ask for?!

  • Julie Nov 2025 · via hotels.com
    3/5

    Air and heat broken in room.

  • Laura Nov 2025 · via hotels.com
    5/5

    The staff was great. The hotel was really cool. It preserved the historical aspects of the building and udated where it needed to. The restaurant was great and the server was super nice. I also loved the refillable water bottle and sparkling water!

  • Keith Nov 2025 · via expedia
    5/5

    Great location and room for the price. Restaurant downstairs is also very nice if you wanted to grab a meal without leaving. Only a few hundred yards from Blue Line stop which goes right to the airport, and the welcome drink was a nice touch. Staff was also super friendly and accommodating.

  • Jean Nov 2025 · via hotels.com
    4/5

    Awesome location! Great bar and food! Best value in this area for sure!

  • Gil Nov 2025 · via hotels.com
    5/5

    Great views, quiet

  • Pranav Nov 2025 · via expedia
    5/5

    Fantastic room and hotel. Free drink too.

  • James Nov 2025 · via expedia
    5/5

    Nice friend staff, great atmosphere.

  • Julie Nov 2025 · via expedia
    5/5

    Such a fun vibe! Cute theme. Great amenities. Super clean. Convenient location.

  • Shawn Nov 2025 · via expedia
    5/5

    The room we had was ckean

  • Kelly Nov 2025 · via hotels.com
    5/5

    Incredibly friendly front desk staff! Hotel was very clean and comfortable. Wish the bar was open later on a Saturday night

  • Kevin Nov 2025 · via expedia
    5/5

    Amazing location. Room was great, and staff were excellent. The food in the hotel restaurant was fantastic. Would stay again the next time we visit Chicago.

  • David Nov 2025 · via hotels.com
    5/5

    The room was pleasant, though there was a stain in the bath tub. The bed was very comfortable and I slept like a stone. However I had some difficulty using ithe TV remote control, the battery may need to be replaced. The staff is wonderful. Sashon at the front desk was very helpful in resolving a transportation problem. Altogether a very pleasant stay.

  • Matthew Oct 2025 · via expedia
    4/5

    Nice room. Historic property, which was fun. Paid a resort fee after I clicked through on Expedia (I had the option to cancel, but did not). Should have included fee coffee in the AM (there is in the room, but not in lobby). Got to use one of the two free drink coupons; only included wine and beer. Overall nice/okay, not outstanding.

  • MIRELKA Oct 2025 · via expedia
    5/5

    Great Staff

  • Mark Oct 2025 · via expedia
    5/5

    Super friendly staff and great central location.

  • Frank Oct 2025 · via expedia
    5/5

    Clean room with high ceiling

  • Eric Oct 2025 · via hotels.com
    5/5

    Clean room, restaurant food was good, staff polite. Appreciated the historical feel and visually appealing interior of the hotel.

  • Rebecca Oct 2025 · via hotels.com
    5/5

    The room was small, but comfortable. The bathroom was a slightly odd logout because the door opened in right in front of the vanity so it was impossible to have the door open and stand in front of the vanity at the same time.

  • Earl Oct 2025 · via expedia
    3/5

    Floor outside of shower was also dirty.

  • Gail Oct 2025 · via hotels.com
    3/5

    The hotel was lovely but there were hidden charges for wi fi and free coffe and cookies, the receptionist insisted on taking payment first before telling us what it was for and we could not opt out.

  • Joseph Oct 2025 · via hotels.com
    5/5

    Very clean and fun.

  • Andrew Oct 2025 · via hotels.com
    5/5

    Great

  • Lauren Oct 2025 · via hotels.com
    4/5

    Great location and staff. Terrible parking options.

  • Ryan Oct 2025 · via expedia
    5/5

    c

  • brittany Oct 2025 · via expedia
    5/5

    Staff was excellent , a great central spot to stay in Chicago.

  • Bob Sep 2025 · via expedia
    5/5

    All good

  • margot Sep 2025 · via expedia
    4/5

    Everything was great. Wish the robes in the rooms were size inclusive.

  • Marie Sep 2025 · via expedia
    5/5

    We always stay here when we come to Chicago this is our 3rd time at stay pineapple and we will continue to come to this hotel. Staff is always friendly and accommodating and we love the rooms, views, location. Thank you and thank your Chicago staff for always going above and beyond for us. From watching our bags to recommendations and even a friendly chat.

  • Stacy Sep 2025 · via expedia
    5/5

    Best hotel ever! The staff was incredible. The location was premium-you could be at the “bean” in a couple minutes!! The bed was so cozy. The place was clean and beautiful. There was a snack daily. It really was so fantastic!

  • Susan Sep 2025 · via hotels.com
    5/5

    Great place to stay! Staff was super friendly. Great amenities as well. Close to Millenium Park and amazing pizza at Paizanos. We plan to stay here on future visits!

  • Arnold Sep 2025 · via expedia
    5/5

    Staff members were extremely and cordial. The property is unique, and the room was lovely. I am often in Chicago, and will make this my "go-to"

  • MARY Sep 2025 · via hotels.com
    5/5

    Great location, views, staff, and building!

  • Anthony Sep 2025 · via expedia
    4/5

    The only down side was not being told the cost of the freebies as that's the way they were labeled in the room.

  • Virginia Sep 2025 · via expedia
    5/5

    Right in the heart of a great shopping area. Atwood Cafe downstairs was a nice place to unwind and have a cocktail.

  • Jennifer Sep 2025 · via hotels.com
    5/5

    Cute hotel. Convenient. Nice for the price.

  • James Sep 2025 · via expedia
    5/5

    Great hotel!!

  • Dalisa Sep 2025 · via expedia
    5/5

    The staff was amazing and very welcoming. It gave very high class! The valet greeted me first and took care of the car the entire trip. He walked my bags in ushering me to the counter and from there the counter took over. We handled check in smoothly and fast. Got to my room and had an amazing view!

  • Donald Sep 2025 · via expedia
    3/5

    This is a great hotel, but I am downgrading it because of its exorbitant and gratuitous Resort Fee, a.k.a.junk fee. Just quote a fair room charge and skip the scam, please.

  • David Sep 2025 · via hotels.com
    5/5

    Well, one thing: the shower head was terrible. Not in keeping with the rest of the experience.

  • Noel Sep 2025 · via hotels.com
    5/5

    Great hotel. Front desk was very outgoing and personable. Convenient location...close to everything.

  • JAMES Sep 2025 · via expedia
    5/5

    The location was excellent! Steps from public transportation, shopping and a few blocks from everything! The property was impeccable. The bedding was lovely. The entire staff was incredibly professional, hospitable and friendly. We had spent our first night at a neighboring hotel, but luckily we changed to his property. Staypineapple has a new fan! Thanks for making our trip to Chicago so memorable!

  • Shelby Sep 2025 · via expedia
    5/5

    LOCATION, LOCATION, LOCATION! We did not have to use any types of transportation besides getting to/from Chicago O’Hare Airport. Everything we needed was within walking distance, including the concert at Soldier Stadium. The staff members were all excellent! We called for extra towels, and the towels arrived at our door within 5 minutes. Our room was clean/quiet/comfortable! I would recommend, and we will definitely be staying here again!

  • Michael Sep 2025 · via expedia
    5/5

    Beautiful building, great customer service and amenities, and awesome location!

  • sewana Sep 2025 · via expedia
    5/5

    The hotel was beautiful and the staff was amazing

  • Katrina Aug 2025 · via expedia
    4/5

    I would recommend that future visitors who are driving park in the Grant Park North garage. Very convenient!

  • Machaelie Aug 2025 · via expedia
    5/5

    Location was outstanding. Atmosphere is great. Most comfortable hotel bed I think I’ve ever slept on. The restaurant is very nice. Staff were so kind and helpful. Will absolutely book again next time we visit Chicago.

  • Ashley Aug 2025 · via hotels.com
    5/5

    Quaint hotel in an amazing location! Staff was friendly hotel and rooms were clean and perhaps the most comfortable bedding I’ve ever experienced!

  • Alison Aug 2025 · via expedia
    5/5

    The gentleman that checked me in was so friendly and accommodating. I travel to Chicago for work, and this is my go to for hotels. It always exceeds every other hotel in the area.

  • Kristina Aug 2025 · via expedia
    5/5

    We loved the experience! We shall come back again😊

  • Aaron Aug 2025 · via expedia
    4/5

    A great place to stay the only problem was my room. It had a strange unpleasant odor. I understand the property is extremely old. Maybe an air diffuse could have worked. However it’s a nice hotel and very conveniently located.

  • Albert Aug 2025 · via hotels.com
    5/5

    Very enjoyable quaint boutique hotel

  • Christie Aug 2025 · via expedia
    5/5

    Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!

  • Edgar Aug 2025 · via hotels.com
    5/5

    Amazing

  • Darla Aug 2025 · via expedia
    4/5

    Streaming service didn’t work on our tv.

  • Andrew Aug 2025 · via hotels.com
    5/5

    Nicely renovated historic building a great Loop location, close to everything. Very well appointed and comfortable room.

  • MARY Aug 2025 · via hotels.com
    5/5

    Love this place. Friendly and welcoming. Lots of free swag.

  • Kenyan Aug 2025 · via expedia
    5/5

    The staff were really friendly, beds super comfy, the hotel was beautiful

  • Jennifer Aug 2025 · via expedia
    5/5

    Great experience and they kept the theme the whole way through

  • Michael Aug 2025 · via expedia
    5/5

    The property is so convenient to everything we want to do.

  • John Aug 2025 · via expedia
    5/5

    Our ONLY criticism is that the bathroom (#805) needed some "deep cleaning": The seal/grout around the tub was mold-stained, and the floor tile grout was in dire need of a good deep cleaning. But for that, everything was pretty much perfect. We love the building, the location, and the view down State Street. The bedding was luxurious, though in the warm weather we wish there was a "lighter" option than the wonderful "coverlet" provided.

  • ronna Aug 2025 · via expedia
    5/5

    Great staff. Nice vibe in the whole place

  • Laura Aug 2025 · via expedia
    5/5

    The property was beautiful and in an amazing location. The staff was wonderful and even kept the restaurant open late for us when we arrived later than anticipated.

  • CYNTHIA Aug 2025 · via expedia
    5/5

    Restaurant had good breakfast

  • Jose Aug 2025 · via expedia
    5/5

    Excellent, definitely will be staying again.

  • Michele Aug 2025 · via expedia
    5/5

    The pineapple theme was fun and quirky and the overall vibe was relaxed and friendly. This was a great place to stay for my quick trip to Chicago!

  • Amanda Aug 2025 · via expedia
    5/5

    The staff is friendly and helpful. The location is convenient. The rooms are clean and the beds are very comfortable. This is as our second time staying here and we will definitely come back a third time.

  • Britany Aug 2025 · via expedia
    5/5

    Clean, unique

  • Victor Jul 2025 · via expedia
    5/5

    I always recommend this hotel to my guests and book travel for other people here. Super friendly awesome staff, great place to stay downtown and very convenient location.

  • Shannon Jul 2025 · via hotels.com
    5/5

    Love staying at this hotel due to stellar location, service, and cleanliness! I am a repeat customer and will be back again soon.

  • Ethel Jul 2025 · via expedia
    5/5

    It was a perfect overnight stay in Chicago. Easy accessibility, clean & helpful staff.

  • Brayan Jul 2025 · via expedia
    5/5

    Great property for experiencing Chicago. All of the L stations are just a few blocks away, giving access to anywhere you could want to go. One block down from Michigan Ave and Millennium Park. Beautiful city views, nothing beats the Chicago Skyline

  • Verified Jul 2025 · via hotels.com
    3/5

    The theme is cute and the offered amenities are nice, but that does not compensate for dusty, dingy rooms and poorly functioning bathrooms.

  • Courtney Jul 2025 · via expedia
    5/5

    Another wonderful stay for my sister’s bachelorette party. The staff were lovely. And the girls specifically stated how great the water pressure was! Oh - and you can’t forget the delicious cookies! Thank you!

  • Karen Jul 2025 · via expedia
    4/5

    The bartender was very nice.

  • Robert Jul 2025 · via expedia
    3/5

    Location was great near multiple lines using CTA in the loop. Also near several restaurants. Bathroom was nice & big. There is a safe in the room. Shower was in the back corner and open concept. There was a curtain to use. Previous reviews were correct about only a fitted sheet; no flat sheet. Only a duvet. Got hot & cold throughout the night; so I did not get good sleep for 3 nights. I do not think the controller on the air conditioner works. The controller was an old school dial that turns to adjust the temp setting because the temp felt the same all the time. Stayed 3 nights & no housekeeping. I made it work by alternating days with 2 towels; hanging the towel after each use. One of the workers was giving me a hard time about being a Cubs fan, & I did not initiate the conversation as I was checking out. Did not appreciate that since I was not a Sox fan. Wish I would have stayed @ the L7.

  • Deanna Jul 2025 · via expedia
    1/5

    Construction was happening right outside at 10pm at night..

  • John Jul 2025 · via expedia
    5/5

    Locations

  • Xiaolin Jul 2025 · via expedia
    5/5

    Great staff and services!

  • Patricia Jul 2025 · via expedia
    5/5

    Staff was extremely helpful and friendly. Room was lovely

  • Jeffry Jul 2025 · via expedia
    5/5

    Very friendly and helpful staff. Great location. Beds are so comfortable

  • Barry Jul 2025 · via hotels.com
    2/5

    The bed was an interesting combination of too small for 2 adults and yet too large for the room, resulting in repeated shin to bed from impacts. The breakfast service was substandard, the coffee a slurry of unfiltered grounds and the leisurely response of the staff resulted in sitting for 10 minutes to make your order. To top the disappointing experience off, the hotel added a so-called 'amenity' fee, which was in fact a cover for adding various state and city taxes to the bill which one might normally expect to be included in a transparent up-front price. Given the hotel already charged Manhattan-scale pricing for the daily rate, this was the final straw. Would definitely NOT stay here again, nor recommend this establishment to others.

  • Florence Jul 2025 · via expedia
    5/5

    Beautiful iconic building, room is clean and comfortable, great pineapple theme everywhere, very convenient location.

  • Katie Jul 2025 · via expedia
    5/5

    The staff were all excellent from the restaurant to the front desk. They also helped us figure out transportation to soldier field, as we are not from a big city and have no idea how that works. The valet was efficient and helpful, the room was so comfortable and clean. The front desk makes sure you are aware of the complimentary pineapple cookies, and where to refill your water bottle. The only noises we heard came from the streets down below. We hated to leave and would love to visit the Stay Pineapple again!

  • Francisco Jul 2025 · via expedia
    5/5

    We were contacted before the check-in to smooth our arrival to the hotel, we really loved the stay and the staff was always supportive, even when we couldn't do a late checkout, they support us storing our luggage during the day. I totally recommend the hotel, the view and all the amenities are great.

  • Nicole Jul 2025 · via expedia
    5/5

    If going to an event near Millennium Park, this is an excellent place to stay. Walkable to the park and many restaurants. It is a historical hotel with great views and amenities.

  • Cindy Jul 2025 · via hotels.com
    5/5

    The hotel was so charming and the location was great for all the things I had planned to do. The room was perfect and bed was very comfortable. Very clean. I will def stay here again!

  • rebecca Jul 2025 · via expedia
    5/5

    It was great. The hotel is perfect

  • Timothy Jul 2025 · via expedia
    5/5

    Perfect location to launch from to see the city.

  • thomas Jul 2025 · via expedia
    5/5

    Folks there were all vibrant, attractive, kind, ambitious, and most of all generous.

  • Amy Jul 2025 · via expedia
    5/5

    Our party of 11 (3 generations in 6 rooms) stayed here for 3 nights, and it was a lovely hotel. The staff is FANTASTIC (especially the breakfast bar/restaurant servers), and the lobby is comfortable and welcoming. And you can't beat the location. When we checked in, they gave a little shoutout to Expedia and offered a little checkin gift in appreciation for our 6-room stay. I thought that was a nice touch. The rooms/bathrooms are a little dated, but the hotel definitely provides lux bedding and lobby amenities to make up for it. Several of us did not like the beds (too soft), so be warned if you can't sleep on a soft bed. But otherwise, we loved this hotel!

  • Maren Jul 2025 · via hotels.com
    5/5

    Do not hesitate to

  • Mary Jul 2025 · via expedia
    5/5

    Loved it

  • CHAUNISHA Jul 2025 · via expedia
    5/5

    Loved everything about it!! Would definitely stay again

  • Jesse Jul 2025 · via hotels.com
    5/5

    The staff was wonderful. The atmosphere was amazing and the decor was on point.

  • Taylor Jul 2025 · via hotels.com
    5/5

    The only thing we didn’t like was the smart TVs didn’t let us stream anything. We didn’t ask for assistance though so it may have been fixable.

  • Kelli Jul 2025 · via expedia
    5/5

    It was very unique, very beautiful. Clean accommodations.

  • Chelsea Jul 2025 · via expedia
    4/5

    Historical building with a few quirks (could use some updating), but service was top notch. And omg the bedding! I slept SO well! Location was perfect, close to lots of things!

  • Ramona Jul 2025 · via expedia
    5/5

    The staff was very welcoming and warm, and the ambience was awesome. Beautiful historic building with amazing design

  • john Jul 2025 · via expedia
    5/5

    Great location and central to everything you could possibly want to walk to in Chicago. Staff were so friendly and helpful. Taxis that were needed when it was not a walkable destination were cheap and easy to access. As was Uber. Highly recommend

  • Kathleen Jun 2025 · via expedia
    5/5

    We would feel better about the daily amenity fee if they offered good coffee in the room, or lobby.

  • Amy Jun 2025 · via expedia
    5/5

    .

  • Vanessa Jun 2025 · via expedia
    5/5

    The staff were fantastic and the building is just beautiful. Our view was amazing!

  • Thomas Jun 2025 · via expedia
    3/5

    Thumbs down on policy of not cleaning rooms every night

  • HEATHER Jun 2025 · via expedia
    5/5

    Great location, multiple food choices and shopping nearby.

  • Lakisha Jun 2025 · via expedia
    5/5

    The hotel was beautiful. Very charming with a historic look and feel, with just the right amount of modern touches. It is conveniently located to an abundance of stores, restaurants, and tourist attractions. All staff members we encountered were extremely helpful and friendly. Just be prepared to pay for valet parking.

  • Thao Jun 2025 · via expedia
    5/5

    Overall great experience. Bed was perfection

  • Paula Jun 2025 · via expedia
    5/5

    Check-in and lobby staff were amazing with us! What a difference it made to feel welcome as soon as we checked-in!

  • Annie Jun 2025 · via hotels.com
    5/5

    Clean, modern and classic. Walking to Bean/ Millennium park , and art museum.

  • jennifer Jun 2025 · via expedia
    5/5

    The staff was welcoming and helpful. Beautiful historic building!

  • Mansooreh Jun 2025 · via expedia
    3/5

    very old carpet and bathroom. there was no even basic stuff there.

  • Paul Jun 2025 · via hotels.com
    5/5

    This is our second stay at this hotel and will probably not be our last visit! Great hotel for the price!

  • Evangelina Jun 2025 · via expedia
    5/5

    The room was amazing! Great service by staff and valet.

  • Eileen Jun 2025 · via expedia
    4/5

    The hotel property is a little tired but that's part of its "iconic" charm. Food in the restaurant was good but the service was spotty, at least at breakfast (ate there three mornings in a row). I had to ask twice to get things I ordered and it was hard to get my server's attention when it was time to pay.

  • Richard Jun 2025 · via hotels.com
    5/5

    This hotel was amazing! The location was central to everything we wanted to do. The L train was yards away. The staff was friendly and helpful in every way. I can’t say enough how much we enjoyed our stay. We will definitely be staying here again!

  • Kyra Jun 2025 · via expedia
    5/5

    Beautiful hotel in a great location.

  • Cassandra Jun 2025 · via hotels.com
    5/5

    Arrived early by train. We were able to check our bags, grabs some water and cookies and then head out for our adventures before the cubs game. Check in was easy. Staff was helpful with directions to L. We were even able to check our bags after check out so we didn’t have to take them around town with us for our last day before going home on the train.

  • Ricky Jun 2025 · via expedia
    5/5

    The location was excellent. Large portions of food served with each meal.

  • Liz Jun 2025 · via hotels.com
    5/5

    We weren't in our rooms except to sleep basically. But the beds and comforters made sleep come easy. Thank you for actually caring about comfort. Sleep is so important. Also appreciated the early check in.

Frequently asked questions about Staypineapple, An Iconic Hotel, The Loop

Does Staypineapple, An Iconic Hotel, The Loop have free Wi-Fi?
Yes, Staypineapple, An Iconic Hotel, The Loop offers free Wi-Fi for all guests.
Does Staypineapple, An Iconic Hotel, The Loop offer parking?
Yes, Staypineapple, An Iconic Hotel, The Loop offers both self-parking and valet parking. Fees may apply.
Does Staypineapple, An Iconic Hotel, The Loop have meeting spaces, conference centers, or conference rooms?
Yes. Staypineapple, An Iconic Hotel, The Loop features meeting spaces and dedicated conference rooms, suitable for corporate meetings and group gatherings. Banquet and reception facilities are also available.
Does Staypineapple, An Iconic Hotel, The Loop have a fitness center?
Yes, Staypineapple, An Iconic Hotel, The Loop features an on-site fitness center for guests. Additional wellness amenities include spa.
Where is Staypineapple, An Iconic Hotel, The Loop located, and how walkable is the area?
Staypineapple, An Iconic Hotel, The Loop is located at 1 W Washington St, Chicago, IL 60601. With a Walk Score of 99, the area is rated Walker's Paradise. Most daily errands can be done on foot — ideal for travelers without a car.

House rules

Check in 4:00 PM
Check out 12:00 PM
Cancellation Not available
Children Not available