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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Logan Square
Best in Chicago, private, amazing garden space
2 bedrooms, 3 beds, 1 private bathroom
9–14 Aug
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4.95 out of 5 average rating, 749 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
4.97 out of 5 average rating, 76 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Jul
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Room in Irving Park
Cozy Room for One In The Company of Cats -Blueline
4.94 out of 5 average rating, 140 reviews, 1 single bed, 1 bathroom
5–10 Jul
Top guest favourite
Flat in West Side
Easy Downtown Access from The Pilsen Haven
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 1 bathroom
4–9 Jul
Top guest favourite
Room in South Side
Private BR;Parking by UofC/HydePark
4.93 out of 5 average rating, 181 reviews, 1 double bed, 1 bathroom
7–12 Sept
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
3–8 Jul
Guest favourite
Apartment in South Side
The Langley Luxe modern style unit
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Top guest favourite
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
5.0 out of 5 average rating, 17 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
4–9 Jul
Luxe
Flat in Chicago Loop
Luxury Downtown 4BR | Exclusive Design PH
4.97 out of 5 average rating, 39 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
2–7 Jul
Guest favourite
Room in Norwood Park
Private Room in Norwood Park
4.98 out of 5 average rating, 41 reviews, 1 bed, 1 bathroom
5–10 Jul
Top guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
5.0 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Hotel in Downtown Chicago
Perfect Destination! Onsite Bar and Restaurant!
1 bedroom, 1 bathroom
5–10 Jul
Guest favourite
Apartment in South Side
The Modern Woodlawn 2 Bed 2 Bath
4.96 out of 5 average rating, 80 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
Home in West Town
Comfortable welcoming stay for business or leisure
New place to stay, 3 bedrooms, 4 beds, 1 bathroom
1–6 Jul
Top guest favourite
Room in Roscoe Village
Spacious garden level suite
4.96 out of 5 average rating, 311 reviews, 1 queen bed, 1 bathroom
1–6 Nov
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 52 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
Top guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul