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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
September 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1
$259
2
$257
3
$254
4
$255
5
$255
6
$254
7
Low
$228
8
$259
9
$306
10
$298
11
$306
12
$416
13
$344
14
$686
15
$735
16
$739
17
$494
18
$412
19
$416
20
$306
21
$384
22
$384
23
$392
24
$384
25
$384
26
$381
27
$383
28
$384
29
$462
30
$693
Cheapest day
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Mid
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Hotels for Mon, Sep 7
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Top rated
Most reviewed
Sofitel Chicago Magnificent Mile
4.6
Pleasant · 4,063 reviews
$228
$228/night · 1n
Book
JW Marriott Chicago
4.5
Pleasant · 3,169 reviews
$257
$257/night · 1n
Book
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