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Search results; Over 1,000 homes in Chicago

Apartment in Chicago
Modern Luxury In Old Town - Sleeps 4
2 bedrooms, 2 beds, 2 private bathrooms
5–10 Sept
,
4.77 out of 5 average rating, 269 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.91 out of 5 average rating, 23 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.97 out of 5 average rating, 95 reviews, 1 bedroom, 1 bed, 1 bathroom
22–27 Jul
Flat in Skokie
Skokie Serenity - 3 queen beds
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 121 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Flat in Forest Park
Walk to Dining & L Train • King Bed • Patio
4.98 out of 5 average rating, 40 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Rooms in Chicago
Historic North Park home
4.97 out of 5 average rating, 113 reviews, 3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
Guest favourite
Place to stay in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
4.9 out of 5 average rating, 49 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Oct
Guest favourite
Place to stay in Chicago
x3 Private room with bath Hyde Park UChicago
5.0 out of 5 average rating, 16 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Aug
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
17–22 Jul
Top guest favourite
Home in Brookfield
Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
4.94 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Flat in Chicago
Chic 3BR Sun-Filled Oasis: Wicker & Logan Square
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Oak Park
Stylish & Spacious Duplex Near Downtown w/Parking
5.0 out of 5 average rating, 86 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
Guest favourite
Place to stay in Bridgeview
Comfortable Private Room with Easy Chicago Access
5.0 out of 5 average rating, 11 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Place to stay in Chicago
Guest room in Dunning, Chicago IL
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Sept
Top guest favourite
Apartment in Chicago
Luxe Loft vibe | King Suite |4BR 3Ba
5.0 out of 5 average rating, 19 reviews, 4 bedrooms, 4 beds, 3 bathrooms
16–21 Aug
Top guest favourite
Room in Chicago
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
4.95 out of 5 average rating, 681 reviews, 3 beds, 1 bathroom
27 Nov – 2 Dec
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
4.96 out of 5 average rating, 161 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug