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
$665
$133/night · 5n
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The Opera House Hotel
8.8Very good · 1,246 reviews
$1,186
$237/night · 5n
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Belveder Grand
9.5Excellent · 3,627 reviews
$1,191
$238/night · 5n
Book
The Meridian Royal
9.2Excellent · 3,722 reviews
$1,984
$397/night · 5n
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Riverside Luxury Collection
9.8Excellent · 2,103 reviews
$2,014
$403/night · 5n
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The Continental
9.9Excellent · 3,493 reviews
$2,033
$407/night · 5n
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