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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.
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 Sun, Jun 7 · $161/night
$161
June 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1
$580
2
$234
3
$232
4
$241
5
$484
6
7
Low
$161
8
$594
9
$929
10
$254
11
$256
12
$230
13
$257
14
$166
15
$919
16
$403
17
$336
18
$251
19
$427
20
$474
21
$167
22
$257
23
$335
24
$333
25
$252
26
$330
27
$339
28
$187
29
$184
30
$187
Cheapest day
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Mid
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Hotels for Fri, Jan 1
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Top rated
Most reviewed
Sofitel Chicago Magnificent Mile
4.6
Pleasant · 4,064 reviews
$212
$212/night · 1n
Book
JW Marriott Chicago
4.5
Pleasant · 3,169 reviews
$273
$273/night · 1n
Book
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