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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Whole Flat in Private Club. Walk to L, Dining & Shows
1 bedroom, 1 bed, 1 shared bathroom
10–15 Aug
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4.91 out of 5 average rating, 591 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 64 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
5–10 Jul
4.98 out of 5 average rating, 81 reviews
Top guest favourite
Room in Chicago
Spacious & serene in hip spot. Sleeps 4.
1 queen bed, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 520 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Rooms in Oak Park
Single bedroom with Asian decor in family home
2 bedrooms, 1 double bed, 1 bathroom
17–22 Aug
4.94 out of 5 average rating, 383 reviews
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
1 single bed, 1 bathroom
5–10 Jul
4.94 out of 5 average rating, 140 reviews
Guest favourite
Room in Chicago
Lovely Front Room in a New Renovated Apartment
2 single beds, 1 bathroom
22–27 Sept
4.91 out of 5 average rating, 103 reviews
Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.99 out of 5 average rating, 346 reviews
Guest favourite
Place to stay in Chicago
Large Brand New Room in Hyde Park Close toDowntown
1 bedroom, 1 queen bed, 1 bathroom
23–28 Oct
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Chicago
Sun filled tranquil 2 br great part of Logan Sq.
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.77 out of 5 average rating, 567 reviews
Top guest favourite
Flat in Chicago
Beautiful 2BR Apartment in Old Town
2 bedrooms, 3 beds, 1 bathroom
6–11 Jul
4.89 out of 5 average rating, 298 reviews
Top guest favourite
Flat in Forest Park
1 bedroom garden apartment in Forest Park
1 bedroom, 2 beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 184 reviews
Top guest favourite
Flat in Chicago
NorthSide Chicago duplex 5-BD,2King size-free park
5 bedrooms, 6 beds, 2 bathrooms
8–13 Nov
4.97 out of 5 average rating, 198 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 52 reviews
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
4.95 out of 5 average rating, 64 reviews
Superhost
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
4.96 out of 5 average rating, 159 reviews