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Cheapest dates for luxury 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 · $166/night
$166
October 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1
$392
2
$311
3
$330
4
$306
5
$384
6
$384
7
$486
8
$394
9
$489
10
11
$478
12
$455
13
$431
14
$384
15
$314
16
$314
17
$455
18
$336
19
$602
20
$445
21
$455
22
$361
23
$306
24
$301
25
$306
26
$322
27
$345
28
$328
29
$337
30
$337
31
Low
$300
Cheapest day
Cheaper
Mid
Priciest
Hotels for Sat, Oct 31
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Cheapest first
Top rated
Most reviewed
JW Marriott Chicago
4.5
Pleasant · 3,169 reviews
$300
$300/night · 1n
Book
Sofitel Chicago Magnificent Mile
4.6
Pleasant · 4,063 reviews
$301
$301/night · 1n
Book
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