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
$501
$167/night · 3n
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Hotel Lumière
9.2Excellent · 1,151 reviews
$532
$177/night · 3n
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The Opera House Hotel
8.8Very good · 1,246 reviews
$872
$291/night · 3n
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Celestine Suites
8.2Very good · 2,865 reviews
$892
$297/night · 3n
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Belveder Grand
9.5Excellent · 3,627 reviews
$918
$306/night · 3n
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The Meridian Royal
9.2Excellent · 3,722 reviews
$1,609
$536/night · 3n
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The Continental
9.9Excellent · 3,493 reviews
$1,639
$546/night · 3n
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The Whitmore
7.2Good · 2,008 reviews
$1,663
$554/night · 3n
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The Grand Palace
7.5Good · 484 reviews
$1,717
$572/night · 3n
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Azure Sky Hotel & Spa
8.5Very good · 1,341 reviews
$1,748
$583/night · 3n
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Riverside Luxury Collection
9.8Excellent · 2,103 reviews
$1,773
$591/night · 3n
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