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

from Sat, Aug 15 · $134/night

May 2026

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Cheapest dayCheaperMidPriciest

Hotels for Sun, Mar 14

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The Ambassador
9.9Excellent · 3,532 reviews
$805
$115/night · 7n
Book
The Opera House Hotel
8.8Very good · 1,246 reviews
$1,564
$223/night · 7n
Book
The Meridian Royal
9.2Excellent · 3,722 reviews
$2,664
$381/night · 7n
Book
The Continental
9.9Excellent · 3,493 reviews
$2,708
$387/night · 7n
Book
The Whitmore
7.2Good · 2,008 reviews
$2,807
$401/night · 7n
Book

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