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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
1
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
June 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1
$293
2
$392
3
$437
4
$417
5
$391
6
$367
7
$416
8
$405
9
$298
10
$415
11
$402
12
$317
13
$554
14
$394
15
$409
16
$282
17
$293
18
$476
19
$570
20
$555
21
Low
$241
22
$413
23
$330
24
$322
25
$442
26
$568
27
$506
28
$248
29
30
Cheapest day
Cheaper
Mid
Priciest
Hotels for Sun, Jun 21
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Cheapest first
Top rated
Most reviewed
Azure Sky Hotel & Spa
8.5
Very good · 1,341 reviews
$241
$241/night · 1n
Book
The Continental
9.9
Excellent · 3,493 reviews
$275
$275/night · 1n
Book
The Whitmore
7.2
Good · 2,008 reviews
$434
$434/night · 1n
Book
The Grand Palace
7.5
Good · 484 reviews
$495
$495/night · 1n
Book
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