492 Properties in Chicago, Illinois, United States of America. March 5, 2026 through March 6, 2026

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Chicago House Music Festival & ConferenceGrant Park Aug 27-31

Milwaukee Brewers vs Chicago CubsWrigley Field Aug 31-Sep 3

Chicago Jazz FestivalMillennium Park Sep 3-7

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eviivo NORAM

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Enjoy the season with activities like ice skating, snowmobiling, or sledding.

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300+ properties available in your date range

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A hotel entrance with a marquee, American flag, and a person standing in front.

Hilton Vacation Club Hotel Blake Chicago

The Loop

9.69.6 out of 10

Exceptionalexceptional

1,297 reviews(1,297 reviews)

$161 nightly

The current price is $191 total

$191 total

Total with taxes and fees

We have 6 left at this price

Tue, Sep 1 - Wed, Sep 2

Tue 1 of September 2026 to Wed 2 of September 2026

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A couple dining at a table with a city view, surrounded by chairs and a variety of dishes.

Hotel Riu Plaza Chicago

Chicago

Breakfast included

9.49.4 out of 10

Exceptionalexceptional

5,113 reviews(5,113 reviews)

$132 off

$179 nightly

The current price is $242 total

$242 total

Total with taxes and fees

We have 4 left at this price

Tue, Sep 1 - Wed, Sep 2

Tue 1 of September 2026 to Wed 2 of September 2026

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A man in a suit sitting by a window with a vase of red flowers.

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

River Hotel

The Loop

8.88.8 out of 10

Excellentexcellent

5,448 reviews(5,448 reviews)

$155 nightly

The current price is $185 total

$185 total

Total with taxes and fees

Mon, Aug 31 - Tue, Sep 1

Mon 31 of August 2026 to Tue 1 of September 2026

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Photo gallery for Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago

Photo gallery for Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Photo gallery for River Hotel

River Hotel