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Search results; Over 1,000 homes in Chicago

Guest favourite
Guest suite in Portage Park
Peaceful Portage Park Apartment
2 bedrooms, 2 beds, 1 private bathroom
29 Aug – 3 Sept
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4.94 out of 5 average rating, 466 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 64 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Lake View
A Whimsical Fairy-tale Loft in Ravenswood Chicago
4.99 out of 5 average rating, 346 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Flat in West Side
Cozy Apartment in Pilsen | 2BR 2B | 15 Min to Town
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Home in West Side
Chicago Row House Garden Apartmt
4.91 out of 5 average rating, 56 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Oct
Guest favourite
Apartment in West Side
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
4.88 out of 5 average rating, 476 reviews, 2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Guest favourite
Room in South Loop
ChicagoChinatownCenterB
4.93 out of 5 average rating, 55 reviews, 1 single bed, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Flat in North Side
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
4.93 out of 5 average rating, 337 reviews, 2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
4.97 out of 5 average rating, 77 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Jul
Guest favourite
Flat in Wicker Park
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Guest favourite
Flat in Chicago Loop
Upscale High-Rise Apt · Rooftop Pool + Views
4.97 out of 5 average rating, 31 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Flat in Albany Park
NorthSide Chicago duplex 5-BD,2King size-free park
4.97 out of 5 average rating, 198 reviews, 5 bedrooms, 6 beds, 2 bathrooms
8–13 Nov
Top guest favourite
Flat in Logan Square
Sun filled tranquil 2 br great part of Logan Sq.
4.77 out of 5 average rating, 567 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Downtown Chicago
Beautiful 2BR Apartment in Old Town
4.89 out of 5 average rating, 298 reviews, 2 bedrooms, 3 beds, 1 bathroom
6–11 Jul
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
4.95 out of 5 average rating, 64 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Top guest favourite
Flat in Logan Square
Fun & cozy getaway w/POOL/game room/FREE parking
4.98 out of 5 average rating, 156 reviews, 1 bedroom, 3 beds, 1 bathroom
12–17 Jul