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331 USD
Staypineapple, An Iconic Hotel, The Loop in Chicago
🌍 United States, Chicago, 1 W Washington St
● Center: 4 km
🌞 Beach - 1.6 km
☎ Phone: +1 312-940-7997Show
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Rooms and prices
2 guests
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Atwood Double room
Wireless internet, air conditioning and bath
Beds:
331 USD
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Burnham Double room
Air conditioning and private bathroom
Beds:
342 USD
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Reliance Double Suite
Air conditioning and private bathroom
Beds:
423 USD
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Burnham room
Air conditioning and private bathroom
Beds:
563 USD
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Millennium Double Suite with park view
Air conditioning and private bathroom
Beds:
634 USD
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Atwood ADA Accessible with Tub Double room
Air conditioning, shower and private bathroom
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Atwood ADA Accessible with Roll-in Shower Double room
Family room with internet, air conditioner and bathroom
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4 x
Burnham Quadruple room
Air conditioning and private bathroom
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Reliance ADA Accessible with Tub Double Suite
Air conditioning and private bathroom
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Description
Hotel opened in 1895, renovated in 1999. In this hotel 122 rooms, 15 floors.
Policies and conditions
- Child policies: Children of all ages are welcome at this property. Additional fees may be charged for children using existing beds. Add the number of children to get a more accurate price.
- Cribs and Extra Beds: For all room types, extra beds cannot be added. Crib policies vary according to room type. Please refer to the relevant room type policy.
- Pets: Pets are allowed Types of pets allowed: dogs Fee: US$25.00 per room per night
- Service animals: Service animals are allowed
- Age Requirements: The main guest checking in must be at least 18 years old
- Paying at the hotel: AmericanExpress, DinersClub, MasterCard, Visa, UnionPay
- Check in time: 16:00. Check out time: 12:00.
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Services and facilities
General
- Air conditioning
- 24-hour reception
- Smoke-free property
- Heating
- Newspapers
- Ticket assistance
- Express check-in/check-out
- Fire Extinguisher
- All Spaces Non-Smoking (public and private)
Rooms
- Non-smoking rooms
- Room service
- Cable TV
- TV
- Hairdryer
- Shower/Bathtub
- Bathrobe
- Slippers
- Toiletries
Accessibility
- Accessibility features
- Wheelchair Accessible
Services and amenities
- Iron and board
- Luggage storage
- Laundry
- Safe-deposit box
- Dry-cleaning
- Shoe shine
- Luggage storage
- Telephone
- Iron
Meals
- Bar
- Coffee/tea for guests
- Restaurant
- Bottled water
Internet
- Free Wi-Fi
Transfer
- Taxi booking
Languages Spoken
- English
- Multi-language staff
Tourist services
- Tour assistance
Recreation
- Bike rental
Parking
- Parking
- Parking nearby
Pool and beach
- Next to the beach
Business
- Event facilities
- Fax and copy machine
- Conference Hall
Sports
- Fitness facilities
- Gym
Beauty and wellness
- First Aid Kit
Pets
- Pets allowed
The nearest beach is located on the distance of 1630 m. It takes 24 minutes To the beach!
Street view
Video: Staypineapple, An Iconic Hotel, The Loop Chicago
Map
Reviews
20.01.2026
Great location, beautiful hotel, plus comfortable and clean rooms made this stay absolutely perfect
14.01.2026
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.
05.01.2026
Rooms were very comfortable. The staff was very friendly upon check in. Loved the location to everything downtown.
30.12.2025
Good location, clean, comfy bed, love the hotel robe, friendly staff, delicious cookies. Bathroom could use some updating but overall great stay.
11.11.2025
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.
03.11.2025
Incredibly friendly front desk staff! Hotel was very clean and comfortable. Wish the bar was open later on a Saturday night
03.11.2025
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.
02.11.2025
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.
06.10.2025
I had a pleasant stay at Staypineapple. The hotel was conveniently located in the heart of town. It was walking distance to major tourist attractions and 2 train stations. Checking in and out was easy and smooth. The room was clean and spacious. I appreciated the welcome drink and afternoon cookies and coffee. Highly recommended!
25.07.2025
The hotel offers attentive and meticulous service, including luggage delivery and valet parking. The hotel's location is excellent, within a 30-minute walk of most major attractions, eliminating the need for a car. The only drawback is the lack of its own parking.
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POIs near hotel
American Writers Museum (6 min)
Dedicated to American literature with interactive exhibits about notable authors.
Pritzker Military Museum & Library (6 min)
Museum and library dedicated to military history and citizen soldier stories.
Vietnam Veterans Memorial (7 min)
Memorial honoring Chicago veterans who served in the Vietnam War.
Home Insurance Building Site (7 min)
Historic site of the first skyscraper built using a steel frame, constructed in 1884.
Begin Route 66 (7 min)
Starting point of the famous U.S. Route 66, known as the Main Street of America.
Cafe and Restaurants near hotel
Restaurant «The Grillroom Chophouse & Wine Bar» (4 min)
33 W Monroe St, Chicago, IL 60603
Reviews18.01.2018
Nice steak house with something on the menu to satisfy all. Service was just fine and the drinks were perfect. Highly recommend.
03.01.2018
Great, old-school Loop chophouse. Wonderful service and it's never very crowded. It's perfect for business lunches. Food is always tasty and never disappoints. Highly recommend!
31.12.2017
Pretty interesting lunch menu with lots of different choices. Prices are high, but this isn't Subway. Food was fine, not great for the prices. Wait staff were very good, especially with a larger party.
21.12.2017
Great service and food! This is hands down the best restaurant prior to seeing Hamilton. Service is professional, as you would expect from a Chicago steakhouse and the food is high quality. Great location and a nice bar for drinks.
09.11.2017
I read the reviews online and made my reservation before seeing Hamilton. My reservation was complete with my remarks we were seeing Hamilton. The restaurant atmosphere was lovely and the food was divine. Our reservation was for 5:45 and we were promptly seated on time. I expected to be in there easily and hour. I thought we'd have enough time to get outside and take a few pictures before we got in line for the show. I read this elsewhere and I have to agree, it was a little too slow. The waiter was fantastic and kind but I didn't think our dessert would ever get to us. Of course you want to be seated in the theater in plenty of time to freshen up, use the restroom, whatever... before you get your seats. Dessert finally arrived at 7:00 p.m. and we had to eat fast even though the theater was across the street so we could get in line and get settled. We didn't get into our seats until 7:20. If the service was't quite so slow, I would easily give 5 stars and two thumbs up but it just shouldn't take 20 min. to get dessert and then not have the time to enjoy it. I would definitely go back but arrange my time better so I don't stress.
Restaurant «Italian Village» (5 min)
71 W Monroe St, Chicago, IL 60603
Reviews20.01.2018
The Italian Village is right in the middle of the loop. This is a three story building with three different themed restaurants. I've only been to the Village which is on the top floor. The atmosphere is great and you feel that you are in Italy. Food and service was great.
20.01.2018
Been here twice in the last year, while on a business trip. Great food! The atmosphere for the most part is good, but the last time I was there we were put in a corner facing the water station... Not the best view. I must say we didn't have a reservation and didn't mind taking what we could. We made the best of it and enjoyed our Pasta!
11.01.2018
I really enjoy going to Italian Village Restaurant. I've eaten here for lunch and foe dinner. All the food I have had was great! The best time I've had was during the Happy Hour time (in the bar). They have half price wines and drinks. They have complementary pizza during the Happy Hour (4:00 to 6:00). Of couse you have to buy drinks to have the pizza but it's worth it. It does get busy in the bar but it's normally a working age group. Bit sometime when there is a show that night it will get very busy. But still a great place to visit and enjoy a good meal.
09.01.2018
I loved this Italian restaurant. It is probably the best Italian restaurant I have ever been in Chicago. The place is amazing very nicely decorated and the menu is excellent.
Prices are actually very good and the sizes are more than generous.
Reserve your table if you want specially in one of the houses if you can.
Prices are actually very good and the sizes are more than generous.
Reserve your table if you want specially in one of the houses if you can.
04.01.2018
I went here with my family before seeing Hamilton in Chicago, and the service is absolutely amazing!
The interior of the restaurant is absolutely gorgeous, and looks like something straight out of a fairy tale- or like some kind of pub from Harry Potter. It's really amazing..
(There were also signed touring cast posters from both Wicked and The Book Of Mormon, which of course excited me)
And the food.
The food is Italian.
That should be enough for you to know that it's good, but if you didn't get the memo-
When you order, you think that you're going to get some pile of instant mashed potatoes and frozen fruit, but you end up with some masterpiece like what I got- which I forgot to take a picture of.
As for customer service, the waiter I had was very friendly, and even asked if we were going to a theatre related performance that day. When we answered yes, he promised to have us out at a reasonable time, which was extremely helpful.
Overall, I 100% recommend this restaurant if you can afford it.
I will never be able to afford it again after the Hamilton tickets, but it was worth a 91$ bill to get to eat here with my four other family members ^-^.
The interior of the restaurant is absolutely gorgeous, and looks like something straight out of a fairy tale- or like some kind of pub from Harry Potter. It's really amazing..
(There were also signed touring cast posters from both Wicked and The Book Of Mormon, which of course excited me)
And the food.
The food is Italian.
That should be enough for you to know that it's good, but if you didn't get the memo-
When you order, you think that you're going to get some pile of instant mashed potatoes and frozen fruit, but you end up with some masterpiece like what I got- which I forgot to take a picture of.
As for customer service, the waiter I had was very friendly, and even asked if we were going to a theatre related performance that day. When we answered yes, he promised to have us out at a reasonable time, which was extremely helpful.
Overall, I 100% recommend this restaurant if you can afford it.
I will never be able to afford it again after the Hamilton tickets, but it was worth a 91$ bill to get to eat here with my four other family members ^-^.
Restaurant «Elephant & Castle» (5 min)
185 N Wabash Ave, Chicago, IL 60601
Reviews20.01.2018
This is a nice place to replicate the British Pub experience. If you like Lamb this is a place for you. Just remember this is very authentic European food. Lots of leafy greens on your food.
15.01.2018
The staff was great and our appetizer was really good, but everyone was a little underwhelmed with their entrees. But I would go there again to see if it was a fluke. They have a very cool menu with lots of options.
04.01.2018
Loved the happy hour. Got there early to get a table and enjoy half off apps and $4 wine glasses. Service was efficient.
28.12.2017
Stopped in for drinks and dessert on one snowy cold Winter evening recently. The bread pudding was superb, I had a pint (or two) of hard cider with it. Kids had an enormous brownie with ice cream on it, which they loved. Will come back soon to try some of the wonderful looking dinner dishes that kept passing by our table. Server was terrific.
26.12.2017
This place is hot or miss. The big guy bartender is great. Fast and nice, always smiles as he gets crushed late night... one of the female bartenders was horrendous. I waited 10 minutes to be greeted, another 5 to get my drinks, and never got my water. The best part is, the manager stood right there and watched haha. Unreal. I definitely won't come back but who cares right
Frequently asked questions about Staypineapple, An Iconic Hotel, The Loop
How much does it cost to stay at Staypineapple, An Iconic Hotel, The Loop?
The cost of staying in Staypineapple, An Iconic Hotel, The Loop depends on the dates, rates, number of guests and other conditions. The minimum estimated price is 331 USD. Enter your dates to see the exact offer prices.
Is it far from Staypineapple, An Iconic Hotel, The Loop to the nearest beach?
It takes 24 minutes to reach to the nearest beach.
Which room categories are available in the Staypineapple, An Iconic Hotel, The Loop?
You can book Atwood Double room, Atwood ADA Accessible with Tub Double room, Atwood ADA Accessible with Roll-in Shower Double room, Burnham room, Burnham Quadruple room, Burnham Double room, Reliance Double Suite, Reliance ADA Accessible with Tub Double Suite, Millennium Double Suite with park view in the hotel. Please check room availability by choosing your dates
What are the check-in and check-out times at Staypineapple, An Iconic Hotel, The Loop?
Check-in at Staypineapple, An Iconic Hotel, The Loop is possible from 16:00, check-out is until 12:00.
Are pets allowed at Staypineapple, An Iconic Hotel, the Loop Chicago?
Yes, pets are welcome at Staypineapple, An Iconic Hotel, the Loop Chicago, but we recommend calling ahead to confirm details (e.g., pet size, fees).
Does Staypineapple, An Iconic Hotel, the Loop Chicago serve breakfast?
No, Staypineapple, An Iconic Hotel, the Loop Chicago does not provide breakfast.
How to get to Staypineapple, An Iconic Hotel, the Loop Chicago from the nearest airport?
The nearest airport is Midway International Airport, located about 23 mins from hotel by car (18.0 km) away.
What’s the cancellation policy at Staypineapple, An Iconic Hotel, the Loop Chicago?
The cancellation policy at Staypineapple, An Iconic Hotel, the Loop Chicago depends on your room type and booking terms.
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Hotel prices for: July - August 2026 calendar
The average hotel price this month is 428 USD The best time to book is July 28, with rates starting from 331 USD
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