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Staypineapple, An Iconic Hotel, The Loop

★★★★ 1 West Washington, Chicago, US

9 guest rating· 1658 reviews

Travelling with a dog

Dogs are welcome at Staypineapple, An Iconic Hotel, The Loop; it lists pets-allowed in its own facility data.

On top of the basics it offers Pet bowls and Pet basket.

About this hotel

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!

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Rooms & rates

Deluxe King Room

Sleeps 2 · 17 m² · Extra-large double bed (Super-king size)

  • Desk
  • Coffee/tea maker
  • Shower
  • Safety deposit box
  • Hair dryer

Deluxe Queen Room

Sleeps 2 · 16 m² · Queen bed

  • Desk
  • Coffee/tea maker
  • Shower
  • Safety deposit box
  • Hair dryer

Executive King Suite

Sleeps 4 · 37 m² · Extra-large double bed (Super-king size)

  • Desk
  • Coffee/tea maker
  • Safety deposit box
  • Hair dryer
  • Mini-fridge

Executive King Suite - Disability Access

Sleeps 4 · 37 m² · Extra-large double bed (Super-king size), Sofa bed

  • Desk
  • Coffee/tea maker
  • Safety deposit box
  • Hair dryer
  • Mini-fridge

Deluxe Queen Room with Two Queen Beds

Sleeps 4 · 16 m² · 2× Queen bed

  • Desk
  • Coffee/tea maker
  • Shower
  • Safety deposit box
  • Hair dryer

Deluxe Queen Mobility Accessible w/Tub

Sleeps 2 · 16 m² · Queen bed

  • Desk
  • Coffee/tea maker
  • Safety deposit box
  • Hair dryer
  • Mini-fridge

Deluxe Two Double Mobility Accessible w/ Roll-in Shower

Sleeps 4 · 16 m² · 2× Double bed

  • Desk
  • Coffee/tea maker
  • Shower
  • Safety deposit box
  • Hair dryer

Reliance King Suite

Sleeps 4 · King bed

  • Desk
  • Bathrobe
  • Private bathroom
  • Telephone
  • Hair dryer

Reliance King Suite Mobility Accessible w/Tub

Sleeps 4 · Sofa bed, King bed

  • Desk
  • Bathrobe
  • Private bathroom
  • Telephone
  • Hair dryer

Millennium Park King Suite

Sleeps 4 · 37 m² · Extra-large double bed (Super-king size)

  • Desk
  • Coffee/tea maker
  • Shower
  • Safety deposit box
  • Hair dryer

Amenities

  • Free WiFi
  • Fitness facilities
  • Private parking
  • Valet parking
  • Air conditioning
  • Pets allowed
  • Pet basket
  • Pet bowls
  • 24-hour front desk
  • Non-smoking rooms
  • Non-smoking throughout
  • Allergy-free room
  • Auditory guidance
  • Cashless payment available
Show all 37 amenities
  • Cleaning standards that are effective against Coronavirus
  • Daily housekeeping
  • Facilities for disabled guests
  • Fire extinguishers
  • First aid kit available
  • Guest rooms disinfected between stays
  • Guests can opt-out any cleaning services during stay
  • Hand sanitizer in guest room and key areas
  • Heating
  • Higher level toilet
  • Invoice provided
  • Key access
  • Laundry washed per local authority guidelines
  • Lift / Elevator
  • Lower bathroom sink
  • Luggage storage
  • Meeting/banquet facilities
  • Sanitized tableware & silverware
  • Smoke alarms
  • Staff adhere to local safety protocols
  • Toilet with grab rails
  • Visual aids: Braille
  • Wheelchair accessible

Location

What guests say91658 reviews

+ Excellent location+ Friendly staff+ Well-maintained hotelPrice concernsSmall room sizeMissing amenities
Cleanliness8.9
Service9.4
Location9.9
Room Quality8.8
Amenities8.4
Value for Money8.3

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

9.0

Big windows cool coffee pot

Jeff · US · 2026-08-25

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

9.0

Beautiful room with nice view and coffee machine. Excellent, helpful staff.

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.

Katarzyna · PL · 2026-08-25

Great Stay!

9.0

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!

I would have liked an option for a quick snack, but there were plenty of places close by.

Tamara · US · 2026-08-23

Know what you're getting

4.0

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 then can fill up with a tap downstairs, and a gym with broken equipment, a single dirty mat, and a weight set missing half its weights (including 20s and 25s). For that, you shouldn't list out that there are amenities, just include that in the total cost. The carpet feels dirty and is just right on top of a hard floor. The tub was in really poor shape. Multiple plugs didn't work or were pushed into the wall. The bed was sagging into a U and my bedding smelled of cigarette smoke. And I wish they were more clear on whether the blankets you get instead of a top sheet are laundered after ever guest. I also feel like the physical key with just a deadbolt is not the safest setup for a hotel room.. As I was leaving, the historic elevators had gone down, too - very grateful that was after my stay, but I feel stressed on behalf of the current guests and housekeeping staff. Great location and good vibes for 2-stars (I do want to give one more shout out to a great staff), but really not great for anything beyond that.

CJ_F3891CI · AUSTIN, TEXAS · 2026-08-20

PawFriendly Stays · questions

Does Staypineapple, An Iconic Hotel, The Loop allow dogs?
Yes, Staypineapple, An Iconic Hotel, The Loop is flagged pet-friendly in its listing. Fees and size limits are set by the hotel; ask at booking if they aren't shown.

Good to know

Reservations for 10 rooms or more need to be contracted as a Group with the hotel directly. Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.

A deposit may be required at the property.