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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
2 King Beds /Easy Downtown / Free Str Parking-Read
2 bedrooms, 4 beds, 1 private bathroom
18–23 Aug
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4.88 out of 5 average rating, 281 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
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 48 reviews
Flat in Chicago
Cozy Apartment in Pilsen | 2BR 2B | 15 Min to Town
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed, 1 bathroom
1–6 Nov
4.96 out of 5 average rating, 312 reviews
Guest favourite
Room in Chicago
ChicagoChinatownCenterB
1 single bed, 1 bathroom
29 Aug – 3 Sept
4.93 out of 5 average rating, 55 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
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
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 52 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
Top guest favourite
Flat in Chicago
Modern & Spacious Condo Minutes from the Loop
3 bedrooms, 3 queen beds, 2 bathrooms
6–11 Sept
4.97 out of 5 average rating, 77 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
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms, 2 bathrooms
14–19 Aug
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 7 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
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 64 reviews
Guest favourite
Flat in Chicago
Spacious 1-bedroom South Loop Loft I Sleep 5
1 bedroom, 4 beds, 1 bathroom
9–14 Aug
4.94 out of 5 average rating, 232 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, 160 reviews