Cheapest dates for 5-star 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 Continental
9.9Excellent · 3,493 reviews
$263
$263/night · 1n
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The Meridian Royal
9.2Excellent · 3,722 reviews
$374
$374/night · 1n
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The Whitmore
7.2Good · 2,008 reviews
$376
$376/night · 1n
Book
Riverside Luxury Collection
9.8Excellent · 2,103 reviews
$385
$385/night · 1n
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Azure Sky Hotel & Spa
8.5Very good · 1,341 reviews
$389
$389/night · 1n
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The Grand Palace
7.5Good · 484 reviews
$408
$408/night · 1n
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