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
$668
$134/night · 5n
Book
Belveder Grand
9.5Excellent · 3,627 reviews
$1,158
$232/night · 5n
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Riverside Luxury Collection
9.8Excellent · 2,103 reviews
$2,037
$407/night · 5n
Book
The Continental
9.9Excellent · 3,493 reviews
$2,072
$414/night · 5n
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The Whitmore
7.2Good · 2,008 reviews
$2,075
$415/night · 5n
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The Grand Palace
7.5Good · 484 reviews
$2,169
$434/night · 5n
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