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
$607
$121/night · 5n
Book
Belveder Grand
9.5Excellent · 3,627 reviews
$1,074
$215/night · 5n
Book
Celestine Suites
8.2Very good · 2,865 reviews
$1,114
$223/night · 5n
Book
Riverside Luxury Collection
9.8Excellent · 2,103 reviews
$1,997
$399/night · 5n
Book
The Grand Palace
7.5Good · 484 reviews
$2,112
$422/night · 5n
Book
The Whitmore
7.2Good · 2,008 reviews
$2,116
$423/night · 5n
Book