Hotel
Dip
Luxury
Cheap
Guides
Sign in
Sign up free
Home
/ Chicago
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.
Destination
Hotel class
5-star (luxury)
4-star+
3-star+
Any class
When
Jun 1 to Sep 1 · Any length
Update
More filters
Cheapest stays in the next 3 months
1 night
from Tue, Jun 2 · $37/night
$37
June 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1
$39
2
Low
$37
3
$40
4
$38
5
$39
6
$56
7
$52
8
$54
9
$49
10
$49
11
$50
12
$53
13
$52
14
$52
15
$50
16
$49
17
$49
18
$50
19
$55
20
$51
21
$58
22
$55
23
$56
24
$55
25
$54
26
$60
27
$59
28
$50
29
$54
30
$50
Cheapest day
Cheaper
Mid
Priciest
Hotels for Sun, May 2
Sort
Cheapest first
Top rated
Most reviewed
Millennium Hotel Knickerbocker Chicago
3.9
Pleasant · 3,873 reviews
$145
$145/night · 1n
Book
Club Quarters Hotel Wacker at Michigan, Chicago
4.1
Pleasant · 1,363 reviews
$183
$183/night · 1n
Book
The Congress Plaza Hotel & Convention Center
3.7
Pleasant · 7,843 reviews
$322
$322/night · 1n
Book
More for Chicago
Best time to visit Chicago
Luxury in Chicago
5-star in Chicago
Cheap in Chicago
Beachfront in Chicago
Spa in Chicago
Pet-friendly in Chicago
