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
$646
$129/night · 5n
Book
Belveder Grand
9.5Excellent · 3,627 reviews
$1,150
$230/night · 5n
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Celestine Suites
8.2Very good · 2,865 reviews
$1,218
$244/night · 5n
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Azure Sky Hotel & Spa
8.5Very good · 1,341 reviews
$1,916
$383/night · 5n
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The Grand Palace
7.5Good · 484 reviews
$1,978
$396/night · 5n
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Riverside Luxury Collection
9.8Excellent · 2,103 reviews
$2,008
$402/night · 5n
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