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

Hotel Lumière
9.2Excellent · 1,151 reviews
$83
$83/night · 1n
Book
The Ambassador
9.9Excellent · 3,532 reviews
$136
$136/night · 1n
Book
Celestine Suites
8.2Very good · 2,865 reviews
$224
$224/night · 1n
Book
Belveder Grand
9.5Excellent · 3,627 reviews
$264
$264/night · 1n
Book
The Continental
9.9Excellent · 3,493 reviews
$327
$327/night · 1n
Book
Riverside Luxury Collection
9.8Excellent · 2,103 reviews
$338
$338/night · 1n
Book
The Whitmore
7.2Good · 2,008 reviews
$402
$402/night · 1n
Book
Azure Sky Hotel & Spa
8.5Very good · 1,341 reviews
$449
$449/night · 1n
Book
The Meridian Royal
9.2Excellent · 3,722 reviews
$459
$459/night · 1n
Book
The Grand Palace
7.5Good · 484 reviews
$476
$476/night · 1n
Book