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
$621
$124/night · 5n
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Belveder Grand
9.5Excellent · 3,627 reviews
$1,074
$215/night · 5n
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Celestine Suites
8.2Very good · 2,865 reviews
$1,151
$230/night · 5n
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Azure Sky Hotel & Spa
8.5Very good · 1,341 reviews
$1,977
$395/night · 5n
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The Continental
9.9Excellent · 3,493 reviews
$1,994
$399/night · 5n
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Riverside Luxury Collection
9.8Excellent · 2,103 reviews
$2,088
$418/night · 5n
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