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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
April 2027
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1
$402
2
$349
3
$526
4
$225
5
$267
6
$252
7
$386
8
$400
9
$500
10
$507
11
$353
12
$230
13
$343
14
$361
15
$450
16
$347
17
$354
18
$354
19
Low
$225
20
$252
21
$363
22
$327
23
$447
24
$387
25
$284
26
$255
27
$351
28
$269
29
$404
30
$459
Cheapest day
Cheaper
Mid
Priciest
Hotels for Mon, Apr 19
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Cheapest first
Top rated
Most reviewed
The Whitmore
7.2
Good · 2,008 reviews
$225
$225/night · 1n
Book
The Grand Palace
7.5
Good · 484 reviews
$246
$246/night · 1n
Book
The Continental
9.9
Excellent · 3,493 reviews
$388
$388/night · 1n
Book
Azure Sky Hotel & Spa
8.5
Very good · 1,341 reviews
$418
$418/night · 1n
Book
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