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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 · $166/night
$166
December 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1
$320
2
$311
3
$239
4
$239
5
$293
6
$239
7
$239
8
$239
9
$239
10
$239
11
$239
12
$239
13
Low
$194
14
$194
15
$203
16
$203
17
$194
18
$194
19
$203
20
$194
21
$194
22
$194
23
$194
24
$194
25
$194
26
$195
27
$194
28
$194
29
$194
30
$194
31
$347
Cheapest day
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Hotels for Sun, Dec 13
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Top rated
Most reviewed
Sofitel Chicago Magnificent Mile
4.6
Pleasant · 4,064 reviews
$194
$194/night · 1n
Book
JW Marriott Chicago
4.5
Pleasant · 3,169 reviews
$291
$291/night · 1n
Book
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