Compare luxury hotels in Chicago by location, guest rating signals, room rules, amenities, cancellation flexibility, and total stay cost before you book.
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Luxury in Chicago is decided by location and service level, not by the star number on the listing — The Loop is where the trip works on foot. Compare suite options and what the rate includes rather than the rating alone.
Rates, availability and fees change by date. Confirm them in live search for your own dates.
location, star rating, guest rating volume, suite options, dining, spa, and service level
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Rated 7.5+ out of 10 by guests across 100+ reviews, most-reviewed first. Open a hotel to see rooms and prices for your dates.
On average, the cheapest month to stay in Chicago is February 2027 at $236 a night, and the most expensive is June 2027 at $592 a night. Across the months shown, the average is $410 a night.
| Check-in month | Average per night | Average per night |
|---|---|---|
| October 2026 | $491 | |
| November 2026 | $329 | |
| December 2026 | $254 | |
| January 2027 | $241 | |
| February 2027Cheapest | $236 |
9.0/10 · 2,699 guest reviews
500 South Dearborn Street
| March 2027 | $292 |
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| April 2027 | $397 |
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| May 2027 | $485 |
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| June 2027Most expensive | $592 |
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| July 2027 | $553 |
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| August 2027 | $524 |
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| September 2027 | $547 |
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Average nightly room price across up to 1,000 hotels in the city for each check-in date in the next 12 months, in US dollars, as quoted to Fly2Any on October 13, 2026. A planning guide, not a fare: search your dates for live prices.
