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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
November 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1
$259
2
$306
3
$306
4
$306
5
$301
6
$346
7
$411
8
$259
9
$252
10
$259
11
$259
12
$252
13
$297
14
$299
15
$252
16
$259
17
$259
18
$301
19
$306
20
$223
21
$300
22
$189
23
$189
24
Low
$184
25
$189
26
$189
27
$276
28
$283
29
$249
30
$339
Cheapest day
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Mid
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Hotels for Tue, Nov 24
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Cheapest first
Top rated
Most reviewed
Sofitel Chicago Magnificent Mile
4.6
Pleasant · 4,063 reviews
$184
$184/night · 1n
Book
JW Marriott Chicago
4.5
Pleasant · 3,169 reviews
$331
$331/night · 1n
Book
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