Cheapest dates for Any class hotels in Chicago

Stay flexible and book the dip. Greener days are cheaper, so tap a day to see hotels.

Cheapest stays in the next 3 months

May 2026

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The Ambassador
9.9Excellent · 3,532 reviews
$444
$148/night · 3n
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Hotel Lumière
9.2Excellent · 1,151 reviews
$454
$151/night · 3n
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The Opera House Hotel
8.8Very good · 1,246 reviews
$844
$281/night · 3n
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Celestine Suites
8.2Very good · 2,865 reviews
$848
$283/night · 3n
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Belveder Grand
9.5Excellent · 3,627 reviews
$859
$286/night · 3n
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Azure Sky Hotel & Spa
8.5Very good · 1,341 reviews
$1,289
$430/night · 3n
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The Continental
9.9Excellent · 3,493 reviews
$1,301
$434/night · 3n
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Riverside Luxury Collection
9.8Excellent · 2,103 reviews
$1,385
$462/night · 3n
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The Whitmore
7.2Good · 2,008 reviews
$1,447
$482/night · 3n
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The Meridian Royal
9.2Excellent · 3,722 reviews
$1,509
$503/night · 3n
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The Grand Palace
7.5Good · 484 reviews
$1,545
$515/night · 3n
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