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Cheapest dates for beachfront 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
May 29 to Aug 29 · Any length
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More filters
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Vibe and amenities
Boutique
Beachfront
Waterfront
Pet-friendly
Adults-only
Spa
Romantic
Pool
Family-friendly
Minimum guest rating
Any rating
8.0+ Very good
9.0+ Excellent
Cheapest stays in the next 3 months
1 night
from Sun, Jun 21 · $241/night
$241
February 2027
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1
$297
2
$300
3
$238
4
$264
5
$409
6
$411
7
$349
8
$343
9
$251
10
$328
11
$248
12
$307
13
$311
14
$285
15
Low
$195
16
$265
17
$317
18
$288
19
$398
20
$420
21
$341
22
$305
23
$239
24
$227
25
$256
26
$411
27
$284
28
$253
Cheapest day
Cheaper
Mid
Priciest
Hotels for Mon, Feb 15
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Cheapest first
Top rated
Most reviewed
The Grand Palace
7.5
Good · 484 reviews
$195
$195/night · 1n
Book
Azure Sky Hotel & Spa
8.5
Very good · 1,341 reviews
$340
$340/night · 1n
Book
The Continental
9.9
Excellent · 3,493 reviews
$368
$368/night · 1n
Book
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