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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Chicago
The Urban Oasis | Outdoor Lounge • Sleeps 10+
4 bedrooms, 7 beds, 2.5 private bathrooms
26–31 Jul
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4.93 out of 5 average rating, 169 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
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, 1 bathroom
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, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Chicago
Fully Furnished Apartment Wicker Park Free Parking
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 617 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 19 reviews
Guest favourite
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, 161 reviews
Top guest favourite
Flat in Chicago
Modern Luxe Retreat in Pilsen’s Colorful Center
2 bedrooms, 2 queen beds, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
29 Aug – 3 Sept
4.96 out of 5 average rating, 300 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
6–11 Dec
4.99 out of 5 average rating, 108 reviews
Guest favourite
Flat in Chicago
Millennium Park 10 Min, Parking, Balcony, Sleeps 8
2 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
4.97 out of 5 average rating, 161 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Guest favourite
Room in Chicago
Lovely Front Room #1 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 802| Gold Coast/Old Town
2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.95 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, 1 bathroom
16–21 Aug
4.77 out of 5 average rating, 568 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
Top guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
4.9 out of 5 average rating, 504 reviews
Guest favourite
Home in Chicago
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 12 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, 54 reviews