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
$138
$138/night · 1n
Book
The Ambassador
9.9Excellent · 3,532 reviews
$140
$140/night · 1n
Book
Celestine Suites
8.2Very good · 2,865 reviews
$192
$192/night · 1n
Book
Belveder Grand
9.5Excellent · 3,627 reviews
$245
$245/night · 1n
Book
The Opera House Hotel
8.8Very good · 1,246 reviews
$259
$259/night · 1n
Book
The Continental
9.9Excellent · 3,493 reviews
$437
$437/night · 1n
Book
The Whitmore
7.2Good · 2,008 reviews
$446
$446/night · 1n
Book
The Grand Palace
7.5Good · 484 reviews
$470
$470/night · 1n
Book
The Meridian Royal
9.2Excellent · 3,722 reviews
$475
$475/night · 1n
Book
Azure Sky Hotel & Spa
8.5Very good · 1,341 reviews
$487
$487/night · 1n
Book
Riverside Luxury Collection
9.8Excellent · 2,103 reviews
$497
$497/night · 1n
Book