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Staypineapple, An Iconic Hotel, The Loop
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Loop · Chicago · United States

Staypineapple, An Iconic Hotel, The Loop

From US$205 a night — varies by your dates

1 West WashingtonView on map
Exceptional
1,658 reviews
9.0
1 / 33
Facilities for disabled guestsWheelchair accessibleFitness facilitiesParkingPets allowed
Stay1 night

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About this hotel

Staypineapple, An Iconic Hotel, The Loop is a 4-star hotel in Chicago, United States.

Historic Architecture and Luxury Design Experience the grandeur of historic Chicago architecture at Staypineapple, An Iconic Hotel, The Loop. Designed by renowned architect Daniel Burnham, the hotel boasts mosaic floors and marble ceilings, offering a luxurious stay in the heart of Chicago's Loop. Modern Amenities and Stunning Views Indulge in the perfect blend of classic elegance and modern comfort in our rooms. Enjoy white and gray decor with mahogany furnishings, flat-screen TVs, and plush bedding. Upgrade to a suite for breathtaking views of Millennium Park and Lake Michigan. Convenient Location and Special Amenities Explore Chicago's top attractions with ease - from shopping on Michigan Avenue to visiting Millennium Park. Take advantage of our fitness center, bicycle rental service, and special perks for your furry friends. Don't miss out on experiencing Navy Pier and other nearby entertainment venues during your stay. Book now for an unforgettable stay at Staypineapple, An Iconic Hotel, The Loop!

Guest reviews

9.0
Exceptional
1,658 reviews

Timeline — click any square to jump to that review

Aug 2026Aug 2026
Showing 5 of 1,658 reviews
Katarzyna🇵🇱
25 Aug 2026
9.0

Very nice stay! I can recommend this hotel to all travelers.

Pros: Beautiful room with nice view and coffee machine. Excellent, helpful staff. Cons: There was a problem with the room at the beginning. But the staff solved that problem immediately - I got another excellent room with beautiful view. Thank you! It's a pity that the hotel doesn't serve breakfast.

Jeff🇺🇸
25 Aug 2026
9.0

Good location, nice historic building with large windows and high ceilings, cool in-room coffee system.

Big windows cool coffee pot

Tamara🇺🇸
23 Aug 2026
9.0

Great Stay!

Pros: The beds were so comfortable, the staff was amazing, and the location was excellent. The little extras were so sweet. I also loved the shampoo, which I rarely say! Cons: I would have liked an option for a quick snack, but there were plenty of places close by.

CJ_F3891CI🌐
20 Aug 2026
4.0

Know what you're getting

If you are looking for a 2-star hotel, this is a great stay. If you are expecting 4-star, you will be deeply disappointed, at best. Great staff - so friendly, accommodating, and efficient. For a 2-star hotel, they seek to add some fun, appreciated touches (the wine and cookies at arrival were a godsend after a long travel day). I appreciated the robe, charging station at the desk, and that the heat worked well. For a 4-star, however, tougher experience. The $25 amenity fee is for a the glass of wine and afternoon cookies, bike rental which I bet few ever use, a single water bottle that you the

Carol🇺🇸
18 Aug 2026
10.0

A nice experience! Well positioned, great breakfast lovely rooms and nicely appointed

Pros: Location iconic beautifully presented Cons: One of the lights didn't work and it would have been nice if there were two drinking flasks instead of one.

Typical weather

October here averages 12°C, with around 99 mm of rain across the month.

Climate data: NASA POWER

Twenty-year averages for this area, not a forecast.

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