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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Lake View
Wrigleyville/Boystown/Entire Private Floor!
1 bedroom, 3 beds, 1 private bathroom
14–19 Oct
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4.85 out of 5 average rating, 282 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
7–12 Jul
4.98 out of 5 average rating, 82 reviews
Top guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 21 reviews
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
9–14 Aug
New place to stay
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds
16–21 Aug
4.95 out of 5 average rating, 107 reviews
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Apartment in Wicker Park
Luxury Oasis in the Heart of the City w Roof Deck
3 bedrooms, 3 beds
5–10 Jul
New place to stay
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms, 5 beds
10–15 Aug
Guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 64 reviews
Luxe
Flat in Chicago Loop
Luxury Downtown 4BR | Exclusive Design PH
4 bedrooms, 5 beds
6–11 Jul
4.98 out of 5 average rating, 40 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds
4–9 Aug
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Apartment in Wrigleyville
Wrigleyville Updated Condo with Free Parking
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 101 reviews
Guest favourite
Apartment in West Side
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds
16–21 Aug
4.88 out of 5 average rating, 476 reviews
Guest favourite
Home in Ukrainian Village
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds
15–20 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Humboldt Park
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Superhost
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
15–20 Aug
4.96 out of 5 average rating, 160 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Townhouse in West Loop
Spacious 3-Bed West Loop Townhouse, 1 Car Garage
3 bedrooms, 6 beds
12–17 Jul
4.97 out of 5 average rating, 36 reviews