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Search results showing properties in Chicago, IL, United States of America (CHI-All Airports). May 21, 2024 through May 26, 2024

Google map showing 430 properties

Chicago is popular!

Only 11% of properties are available on our site for your dates.

Photo gallery for Country Guesthouse at Wind Ridge Herb Farm

Front view of the guesthouse from the garden.
Premier Host
House

Country Guesthouse at Wind Ridge Herb Farm

Sleeps 6 · 3 bedrooms · 1 bathroom
9.8 out of 10 Exceptional (58 reviews)
The price is $137
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Photo gallery for Beautiful Spa Like Suite on the North side!

Image of Beautiful Spa Like Suite on the North side!
Condo · Within North Center

Beautiful Spa Like Suite on the North side!

Sleeps 2 · 1 bedroom · 1 bathroom
9.0 out of 10 Wonderful (8 reviews)
The price is $229
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Photo gallery for Sonder Market Hall | Studio Apartment w/ City View

Room
Premier Host
Apartment · Within Downtown Chicago

Sonder Market Hall | Studio Apartment w/ City View

Sleeps 2 · 1 bathroom
Free cancellation until May 18
8.4 out of 10 Very Good (15 reviews)
The price is $279
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House

Sanctuary Woodland Guest House, located next to the conservation area!

Sleeps 4 · 2 bedrooms · 1 bathroom
10 out of 10 Exceptional (10 reviews)
The price is $130
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House · 4 min walk to Lee Street Beach

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

Sleeps 3 · 1 bedroom · 1 bathroom
10 out of 10 Exceptional (13 reviews)
The price is $239
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House · 12 min walk to Oak Street Beach

Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!

Sleeps 3 · 1 bedroom · 1 bathroom
10 out of 10 Exceptional (2 reviews)
The price is $254
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House · Within Riverwoods

Master qtr close to nature & easy urban facilities

Sleeps 3 · 1 bedroom · 1 bathroom
9.8 out of 10 Exceptional (41 reviews)
The price is $171
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Apartment · Within Downtown Chicago

Sonder Greektown | One-Bedroom Apartment

Sleeps 4 · 1 bedroom · 1 bathroom
Free cancellation until May 18
9.8 out of 10 Exceptional (9 reviews)
The price is $357
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Apartment · 8 min drive to the beach

The Logan Square Guest House - Classic Vintage Comfort With Free Parking!

Sleeps 5 · 2 bedrooms · 1 bathroom
10 out of 10 Exceptional (7 reviews)
The price is $295
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Apartment · Within Lakeview

Cozy & Modish 1BR Apartment

Sleeps 2 · 1 bedroom · 1 bathroom
7.0 out of 10 Good (11 reviews)
The price is $158
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Condo · 7 min drive to the beach

Quaint Chicago Condo: Near Lincoln Park & DePaul!

Sleeps 3 · 1 bedroom · 1 bathroom
The price is $253
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Apartment · 6 min drive to the beach

Exquisite Rogers Park 1bd/1bath Apt. Near Evanston

Sleeps 3 · 1 bedroom · 1 bathroom
9.6 out of 10 Exceptional (15 reviews)
The price is $149
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Cottage · 0.9 mi (1.4 km) to Chemung center

Peaceful Harvard Vacation Rental: 3 Mi to Town!

Sleeps 3 · 1 bedroom · 1 bathroom
10 out of 10 Exceptional (4 reviews)
The price is $109
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Apartment · 0.6 mi (0.9 km) to Pecatonica center

Quite- relaxing country living with pool/hot tub and sauna!

Sleeps 2 · 1 bedroom · 1 bathroom
10 out of 10 Exceptional (13 reviews)
The price is $175
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Apartment · 10 min drive to the beach

Found Chicago powered by Sonder | Queen Room

Sleeps 2 · 1 bathroom
Free cancellation until May 18
9.0 out of 10 Wonderful (7 reviews)
The price is $224
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Apartment · 6 min drive to the beach

"Bliss of Evanston" 180°view, 2BDR +2Bath UrbanLux

Sleeps 5 · 2 bedrooms · 2 bathrooms
10 out of 10 Exceptional (16 reviews)
The price is $317
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House · 2.4 mi (3.8 km) to Rockford center

Nicely Appointed Budget Stay in Rockford

Sleeps 4 · 2 bedrooms · 1 bathroom
10 out of 10 Exceptional (1 review)
The price is $90
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