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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
January 2027
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1
$212
2
$212
3
Low
$194
4
$194
5
$194
6
$194
7
$194
8
$194
9
$194
10
$194
11
$195
12
$194
13
$194
14
$194
15
$194
16
$195
17
$194
18
$194
19
$194
20
$194
21
$194
22
$194
23
$350
24
$426
25
$523
26
$576
27
$194
28
$194
29
$194
30
$203
31
$194
Cheapest day
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Hotels for Sun, Jan 3
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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
$317
$317/night · 1n
Book
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