Avg. for October
Select dates to see prices and availability
Avg. for October
Nightly prices at Staypineapple, An Iconic Hotel, The Loop average $105 in January, the cheapest month, and $344 in September, the most expensive, based on the last 12 months.
| Month | Average price |
|---|---|
| January | $105 |
| February | $116 |
| March | $133 |
| April | $172 |
| May | $277 |
| June | $317 |
| July | $282 |
| August | $305 |
| September | $344 |
| October | $250 |
| November | $158 |
| December | $130 |
Most expensive: September (~$344)
Cheapest: January (~$105)
Parking
Non-Smoking Rooms
Valet Parking
Housekeeping
Banquet Facilities
Bicycle Rental
State Street (0.1 miles)
Daley Plaza (0.1 miles)
Chicago Theatre (0.2 miles)
James M. Nederlander Theatre (0.2 miles)
Michigan Avenue (0.2 miles)
Goodman Theater (0.2 miles)
5
Room details
Sleeps 2
4
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Sleeps 2
5
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Sleeps 4
7
Room details
Sleeps 4
5
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Sleeps 4
5
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Sleeps 4
5
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Sleeps 4
5
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Sleeps 2
4
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Sleeps 2
4
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Sleeps 4
Based on 1,185 verified reviews
AI-generated summary based on recent guest reviews
At Staypineapple, An Iconic Hotel, The Loop, guests repeatedly highlight the central Loop location, friendly staff, historic charm, and exceptionally comfortable beds, with many also noting clean rooms, nice city views, and convenient touches like refillable water bottles.
Read moreWas this helpful?
Susan
4 weeks ago
·
Stayed 4 nights
Vickie
4 weeks ago
·
Stayed 4 nights
Wan Ting
4 weeks ago
·
Stayed 1 night
Jacob
4 weeks ago
·
Stayed 1 night
Edith
Sep 10, 2026
·
Stayed 1 night
Valet parking is available at the property for a fee of USD 75 per night. No reservation is required for parking.
Pets are allowed at the property with a fee of USD 29.95 per accommodation, per night. Service animals are exempt from fees.
Check-in is at 16:00 and check-out is at 12:00. Early or late check-in/check-out may be available upon request, but additional charges may apply.
The property has limited wheelchair accessibility, including features like step-free entrances and accessible public areas. However, specific details about room accessibility are not provided.
The hotel is centrally located in Chicago, just a 5-minute walk from the Chicago Cultural Center and City Hall. It is 0.4 miles from the Chicago Riverwalk and 0.5 miles from the Art Institute of Chicago.
Children are allowed at the property, and there is no specified minimum age for kids to stay for free.
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Instant AI responses are based on hotel information
Over the next 60–90 days, room rates at Staypineapple, An Iconic Hotel, The Loop in Chicago typically land around $221 a night for two guests, ranging from $188 to $346 on peak dates.
Staypineapple, An Iconic Hotel, The Loop in Chicago undercuts 17 of 20 comparable hotels nearby, while similar properties typically run around $279 a night. The hotel’s downtown Cook County location — a short walk from Michigan Avenue and Millennium Park — and its appeal to couples and business travellers help explain why it sits below the neighborhood median.
January is the cheapest month to stay at Staypineapple, An Iconic Hotel, The Loop in Chicago, averaging $150 a night; June is the priciest month, averaging $402.
The current price at Staypineapple, An Iconic Hotel, The Loop in Chicago is $407 per night for 2 guests, which is high for this hotel: about 15% above its $358 average over the last 60 days. Most nights over that period fell between $195 and $877.
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Average nightly price across deals, with taxes & fees.
Prices in USD for 2 guests, updated daily.