Staypineapple, An Iconic Hotel, The Loop Chicago price comparison: 27 booking sites

Each site's price we recorded, low to high

Going rate: $417 a night all-in. The going rate is the price the largest number of listings that named a room or offered free cancellation agreed on (ties go to the lower price).

One snapshot on October 3, 2026 for Nov 7 to Nov 9, 2 adults, US market, USD. Prices change daily.

All-in means taxes and fees included, as each site reported them to Google Hotels. Each row is that site's lowest listing. Hotel's own site is the seller Google Hotels lists under the hotel's name. The snapshot kept up to 28 listings per hotel, so sites priced above these may be missing.

What we measured at Staypineapple, An Iconic Hotel, The Loop Chicago

Google Hotels listed Staypineapple, An Iconic Hotel, The Loop Chicago as a 4-star hotel. Its all-in going rate, $417 a night, was the 7th lowest of the 14 hotels with an all-in going rate on our Chicago page (they ranged from $153 to $742), and the 4th lowest of the 9 there listed as 4-star. Taxes and fees, as the booking sites reported them to Google Hotels, added $67 (19%) to its before-tax going rate of $350, the highest share of the 14 hotels with both prices on our Chicago page (they ranged from 14% to 19%); our data does not split it into taxes and fees. 11 of the 27 booking sites listed exactly the going rate. The highest, $426 on Long Stay Discounts, was 24% above the lowest. 5 of the 27 sites named a room on their lowest listing: the hotel's own site, Expedia.com, Hotels.com, Travelocity.com and Booking.com. 2 of the 27 sites showed free cancellation on their lowest listing; the lowest of those was $370 a night all-in on Billabook.com, $26 above the lowest price.

Questions about Staypineapple, An Iconic Hotel, The Loop Chicago prices