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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Eddy Street Upstairs Apartment
1 bedroom, 1 bed, 1 shared bathroom
8–13 Sept
,
4.95 out of 5 average rating, 169 reviews
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
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Flat in Chicago
Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 64 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.98 out of 5 average rating, 81 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
4.91 out of 5 average rating, 56 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Oct
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Room in Chicago
Spacious & serene in hip spot. Sleeps 4.
4.92 out of 5 average rating, 520 reviews, 1 queen bed, 1 bathroom
16–21 Aug
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
27 Sept – 2 Oct
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Rooms in Oak Park
Single bedroom with Asian decor in family home
4.94 out of 5 average rating, 383 reviews, 2 bedrooms, 1 double bed, 1 bathroom
17–22 Aug
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
4.95 out of 5 average rating, 64 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
4.99 out of 5 average rating, 346 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Top guest favourite
Room in Chicago
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
Guest favourite
Room in Chicago
Lovely Front Room in a New Renovated Apartment
4.91 out of 5 average rating, 103 reviews, 2 single beds, 1 bathroom
22–27 Sept
Guest favourite
Place to stay in Chicago
Large Brand New Room in Hyde Park Close toDowntown
4.95 out of 5 average rating, 21 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Oct
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Flat in Chicago
Sun filled tranquil 2 br great part of Logan Sq.
4.77 out of 5 average rating, 567 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
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Flat in Forest Park
1 bedroom garden apartment in Forest Park
4.98 out of 5 average rating, 184 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Sept – 3 Oct
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Flat in Chicago
Beautiful 2BR Apartment in Old Town
4.89 out of 5 average rating, 298 reviews, 2 bedrooms, 3 beds, 1 bathroom
6–11 Jul
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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
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Flat in Chicago
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 Chicago
NorthSide Chicago duplex 5-BD,2King size-free park
4.97 out of 5 average rating, 198 reviews, 5 bedrooms, 6 beds, 2 bathrooms
8–13 Nov