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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Large Remodeled Home in Lincoln Park, Sleeps 12!
4 bedrooms, 5 beds, 3 private bathrooms
13–18 Sept
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4.97 out of 5 average rating, 147 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
Top guest favourite
Flat in Chicago
Fully Furnished Apartment Wicker Park Free Parking
1 bedroom, 1 queen bed
9–14 Nov
4.97 out of 5 average rating, 628 reviews
Top guest favourite
Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
1 bedroom, 2 beds
13–18 Dec
4.96 out of 5 average rating, 597 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
1–6 Sept
4.88 out of 5 average rating, 141 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
2–7 Nov
4.96 out of 5 average rating, 310 reviews
Guest favourite
Flat in Chicago
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds
13–18 Sept
4.94 out of 5 average rating, 271 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 60 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
6–11 Jan
4.95 out of 5 average rating, 130 reviews
Top guest favourite
Apartment in Chicago
Bright and Sunny 2 BR Condo - Wrigley/Lincoln Park
2 bedrooms, 2 beds
29 Nov – 4 Dec
4.99 out of 5 average rating, 170 reviews
Superhost
Apartment in Chicago
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds
18–23 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Townhouse in Oak Park
A Pleasant Stay in Oak Park
2 bedrooms, 2 beds
9–14 Nov
4.96 out of 5 average rating, 81 reviews
Top guest favourite
Flat in Chicago
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds
1–6 Nov
5.0 out of 5 average rating, 63 reviews
Top guest favourite
Guest house in Chicago
Cozy Coach House
1 queen bed
6–11 Sept
4.96 out of 5 average rating, 509 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 121 reviews
Superhost
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chicago
Top Floor Escape | Modern Amenities | Lush Garden
2 bedrooms, 2 beds
15–20 Nov
4.97 out of 5 average rating, 497 reviews
Guest favourite
Guest suite in Chicago
Peaceful Portage Park Apartment
2 bedrooms, 2 beds
1–6 Nov
4.94 out of 5 average rating, 474 reviews
Guest favourite
Flat in Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds
6–11 Sept
4.95 out of 5 average rating, 110 reviews