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Cheapest dates for cheap 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
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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 Mon, May 24
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Cheapest first
Top rated
Most reviewed
The Chicago Hotel Collection Magnificent Mile Hotel & Suites
2.6
Pleasant · 1,222 reviews
$305
$305/night · 1n
Book
The Chicago Hotel Collection Wrigleyville
2.0
Pleasant · 284 reviews
$312
$312/night · 1n
Book
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