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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Cheapest dayCheaperMidPriciest

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The Grand Palace
7.5Good · 484 reviews
$322
$322/night · 1n
Book
The Continental
9.9Excellent · 3,493 reviews
$345
$345/night · 1n
Book
The Whitmore
7.2Good · 2,008 reviews
$376
$376/night · 1n
Book
Azure Sky Hotel & Spa
8.5Very good · 1,341 reviews
$402
$402/night · 1n
Book
Riverside Luxury Collection
9.8Excellent · 2,103 reviews
$417
$417/night · 1n
Book