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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest house in Chicago
The Roscoe Village Guesthouse
2 bedrooms, 2 beds, 1 private bathroom
2–7 Aug
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4.91 out of 5 average rating, 205 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.98 out of 5 average rating, 87 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
Top guest favourite
Flat in Chicago
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
Home in Chicago
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
Top guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
4.93 out of 5 average rating, 233 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Guest favourite
Home in Chicago
Lovely 6 Bd Retreat w/ Game Room, Back Deck & Bar
4.98 out of 5 average rating, 81 reviews, 6 bedrooms, 9 beds, 3 bathrooms
12–17 Jul
Top guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
5.0 out of 5 average rating, 19 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
4.94 out of 5 average rating, 141 reviews, 1 single bed, 1 bathroom
19–24 Sept
Luxe
Flat in Chicago
Luxury Downtown 4BR | Exclusive Design PH
4.98 out of 5 average rating, 40 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
8–13 Jul
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
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
4.96 out of 5 average rating, 81 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
Guest house in Chicago
Upscale Wicker Park Retreat
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 8 beds, 3 bathrooms
12–17 Jul
Guest favourite
Place to stay in Bridgeview
Comfortable Private Room with Easy Chicago Access
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
4.99 out of 5 average rating, 348 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Room in Chicago
Spacious garden level suite
4.96 out of 5 average rating, 312 reviews, 1 queen bed, 1 bathroom
5–10 Nov
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 3 bathrooms
10–15 Aug