Staypineapple, An Iconic Hotel, The Loop is at 1 West Washington, Chicago. Guests rate it 9.0 out of 10 across 1,658 reviews. It is 0.1 miles from Chicago Theatre (State Street Theatre marquee). Check-in is from 04:00 PM, check-out by 12:00 PM.
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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!
Summarised from guest reviews. Scores out of 10.
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.
The cheapest month to stay at Staypineapple, An Iconic Hotel, The Loop is February 2027, averaging $200 a night; the most expensive is June 2027 at $562. On average it runs 17% below the Chicago hotel average.
| Check-in month | Average per night | Average per night |
|---|---|---|
| October 2026 | $487 | |
| November 2026 | $292 | |
| December 2026 | $214 | |
| January 2027 | $201 | |
| February 2027Cheapest | $200 | |
| March 2027 | $216 | |
| April 2027 | $334 | |
| May 2027 | $429 | |
| June 2027Most expensive | $562 | |
| July 2027 | $532 | |
| August 2027 | $317 |
Average nightly room price at this hotel for each check-in date in the next 12 months, in US dollars, as quoted to Fly2Any on October 12, 2026. A planning guide, not a fare: search your dates for live prices.
Check-in at Staypineapple, An Iconic Hotel, The Loop is from 04:00 PM and check-out is by 12:00 PM.
Yes. Chicago Theatre (State Street Theatre marquee) is 0.1 miles from Staypineapple, An Iconic Hotel, The Loop in a straight line.
Guests rate Staypineapple, An Iconic Hotel, The Loop 9.0 out of 10 across 1,658 reviews. They most often mention excellent location and friendly staff.
Yes. Staypineapple, An Iconic Hotel, The Loop lists free wifi among its amenities. Confirm details with the property for your dates.
Yes. Staypineapple, An Iconic Hotel, The Loop lists a fitness center among its amenities. Confirm details with the property for your dates.
The cheapest month to stay at Staypineapple, An Iconic Hotel, The Loop is February 2027, averaging $200 a night; the most expensive is June 2027 at $562. On average it runs 17% below the Chicago hotel average.
