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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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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
May 2026
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$493
31
Low
$418
Cheapest day
Cheaper
Mid
Priciest
Hotels for Sun, Feb 14
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Cheapest first
Top rated
Most reviewed
Azure Sky Hotel & Spa
8.5
Very good · 1,341 reviews
$285
$285/night · 1n
Book
The Grand Palace
7.5
Good · 484 reviews
$311
$311/night · 1n
Book
The Continental
9.9
Excellent · 3,493 reviews
$312
$312/night · 1n
Book
The Whitmore
7.2
Good · 2,008 reviews
$342
$342/night · 1n
Book
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