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

Sun

Mon

Tue

Wed

Thu

Fri

Sat

Cheapest dayCheaperMidPriciest

Sort

The Ambassador
9.9Excellent · 3,532 reviews
$1,000
$143/night · 7n
Book
Hotel Lumière
9.2Excellent · 1,151 reviews
$1,028
$147/night · 7n
Book
The Opera House Hotel
8.8Very good · 1,246 reviews
$1,781
$254/night · 7n
Book
Belveder Grand
9.5Excellent · 3,627 reviews
$1,805
$258/night · 7n
Book
Celestine Suites
8.2Very good · 2,865 reviews
$1,821
$260/night · 7n
Book
Azure Sky Hotel & Spa
8.5Very good · 1,341 reviews
$3,083
$440/night · 7n
Book
The Meridian Royal
9.2Excellent · 3,722 reviews
$3,204
$458/night · 7n
Book
The Whitmore
7.2Good · 2,008 reviews
$3,306
$472/night · 7n
Book
The Grand Palace
7.5Good · 484 reviews
$3,319
$474/night · 7n
Book
Riverside Luxury Collection
9.8Excellent · 2,103 reviews
$3,339
$477/night · 7n
Book
The Continental
9.9Excellent · 3,493 reviews
$3,446
$492/night · 7n
Book