Cheapest dates for 5-star 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 Grand Palace
7.5Good · 484 reviews
$293
$293/night · 1n
Book
Azure Sky Hotel & Spa
8.5Very good · 1,341 reviews
$323
$323/night · 1n
Book
The Meridian Royal
9.2Excellent · 3,722 reviews
$411
$411/night · 1n
Book
The Whitmore
7.2Good · 2,008 reviews
$418
$418/night · 1n
Book
Riverside Luxury Collection
9.8Excellent · 2,103 reviews
$426
$426/night · 1n
Book
The Continental
9.9Excellent · 3,493 reviews
$478
$478/night · 1n
Book