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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
August 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1
$580
2
$233
3
$237
4
$373
5
$373
6
$233
7
$237
8
Low
$227
9
$233
10
$233
11
$237
12
$233
13
$237
14
$233
15
$255
16
$253
17
$237
18
$227
19
$237
20
$233
21
$254
22
$233
23
$237
24
$233
25
$237
26
$233
27
$237
28
$250
29
$252
30
$257
31
$252
Cheapest day
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Hotels for Sat, Aug 8
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Top rated
Most reviewed
Sofitel Chicago Magnificent Mile
4.6
Pleasant · 4,063 reviews
$227
$227/night · 1n
Book
JW Marriott Chicago
4.5
Pleasant · 3,169 reviews
$276
$276/night · 1n
Book
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