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Search results; Over 1,000 homes in Chicago

Top guest favourite
Bungalow in Chicago
Chicago Bootlegger House Sleeps 10-20
6 bedrooms, 10 beds, 2 private bathrooms
2–7 Oct
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4.96 out of 5 average rating, 164 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
New place to stay
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 312 reviews
Guest favourite
Flat in Chicago
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 271 reviews
Top guest favourite
Flat in Chicago
Spacious 1-bedroom South Loop Loft I Sleep 5
1 bedroom, 4 beds, 1 bathroom
1–6 Nov
4.94 out of 5 average rating, 246 reviews
Top guest favourite
Flat in Chicago
Chic & Cozy Boho Vibe in Heart of Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
28 Nov – 3 Dec
4.96 out of 5 average rating, 82 reviews
Top guest favourite
Flat in Chicago
Your Logan Square Oasis with Lush Outdoor Haven!
2 bedrooms, 2 king beds, 1.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Flat in Forest Park
Sunny 1 bedroom apartment 1 block from restaurants
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 224 reviews
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 bathroom
26–31 Oct
4.92 out of 5 average rating, 72 reviews
Top guest favourite
Apartment in Chicago
Bright and Sunny 2 BR Condo - Wrigley/Lincoln Park
2 bedrooms, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.99 out of 5 average rating, 170 reviews
Superhost
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds, 3 bathrooms
1–6 Nov
4.9 out of 5 average rating, 124 reviews
Superhost
Apartment in Chicago
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 4 reviews
Guest favourite
Townhouse in Oak Park
A Pleasant Stay in Oak Park
2 bedrooms, 2 beds, 1 bathroom
9–14 Nov
4.96 out of 5 average rating, 81 reviews
Top guest favourite
Guest house in Chicago
Cozy Coach House
1 queen bed, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 509 reviews
Guest favourite
Room in Chicago
near festivals & united center
1 bed, 1 bathroom
31 Oct – 5 Nov
4.95 out of 5 average rating, 122 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 122 reviews
Superhost
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Apartment in Chicago
Welcoming 2BR in Chicago's Best Neighborhood!
2 bedrooms, 2 beds, 1 bathroom
17–22 Oct
4.85 out of 5 average rating, 362 reviews
Top guest favourite
Flat in Chicago
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 65 reviews