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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Stone Mansion Sleeps 10-20 Free parking & TV
4 bedrooms, 9 beds, 2 private bathrooms
6–11 Sept
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4.92 out of 5 average rating, 286 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
12–17 Oct
4.95 out of 5 average rating, 120 reviews
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
27 Sept – 2 Oct
4.92 out of 5 average rating, 59 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
25–30 Oct
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 300 reviews
Top guest favourite
Flat in Chicago
Fully Furnished Apartment Wicker Park Free Parking
1 bedroom, 1 queen bed
4–9 Oct
4.98 out of 5 average rating, 617 reviews
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
15–20 Aug
4.96 out of 5 average rating, 161 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 19 reviews
Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds
9–14 Aug
4.93 out of 5 average rating, 235 reviews
Guest favourite
Flat in Chicago
Millennium Park 10 Min, Parking, Balcony, Sleeps 8
2 bedrooms, 4 beds
14–19 Jul
4.97 out of 5 average rating, 161 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
6–11 Dec
4.99 out of 5 average rating, 108 reviews
Guest favourite
Room in Chicago
Lovely Front Room #1 in a New Renovated Apartment
2 single beds
22–27 Sept
4.91 out of 5 average rating, 103 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds
23–28 Aug
4.95 out of 5 average rating, 22 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Chicago
Sun filled tranquil 2 br great part of Logan Sq.
2 bedrooms, 2 queen beds
16–21 Aug
4.77 out of 5 average rating, 568 reviews
Guest favourite
Home in Chicago
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds
15–20 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds
21–26 Sept
4.9 out of 5 average rating, 504 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 54 reviews