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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in South Side
Beautiful European Apartment
3 bedrooms, 4 beds, 1 private bathroom
4–9 Jul
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4.93 out of 5 average rating, 139 reviews
Top guest favourite
Flat in West Side
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 Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Flat in Lake View
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
Apartment in West Side
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.88 out of 5 average rating, 476 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 19 reviews
Flat in West Side
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
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 bathroom
12–17 Oct
4.91 out of 5 average rating, 56 reviews
Guest favourite
Room in South Loop
ChicagoChinatownCenterB
1 single bed, 1 bathroom
29 Aug – 3 Sept
4.93 out of 5 average rating, 55 reviews
Top guest favourite
Flat in North Side
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
4.93 out of 5 average rating, 337 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
4–9 Jul
4.97 out of 5 average rating, 79 reviews
Guest favourite
Flat in Wicker Park
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
Top guest favourite
Flat in Albany Park
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 Logan Square
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
Guest favourite
Flat in North Side
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 Logan Square
Fun & cozy getaway w/POOL/game room/FREE parking
1 bedroom, 3 queen beds, 1 bathroom
12–17 Jul
4.98 out of 5 average rating, 156 reviews
Guest favourite
Flat in Chicago Loop
Upscale High-Rise Apt · Rooftop Pool + Views
1 bedroom, 1 double bed, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 31 reviews
Guest favourite
Flat in South Side
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 Downtown 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