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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Chicago
52nd Floor MagMile Penthouse Views Fireplace Pool
1 bedroom, 2 beds, 1 private bath
Sep 4–9
,
4.81 out of 5 average rating, 79 reviews
Guest favourite
Apartment in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bath
Aug 12–17
4.9 out of 5 average rating, 126 reviews
Guest favourite
Apartment in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 baths
Dec 27–Jan 1
4.95 out of 5 average rating, 127 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed, 1 bath
Sep 20–25
New place to stay
Top guest favourite
Guesthouse in Chicago
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds, 1 bath
Sep 27–Oct 2
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bath
Nov 11–16
4.96 out of 5 average rating, 309 reviews
Top guest favourite
Apartment in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bath
Nov 1–6
4.97 out of 5 average rating, 34 reviews
Guest favourite
Apartment in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds, 2 baths
Aug 15–20
4.87 out of 5 average rating, 15 reviews
Top guest favourite
Apartment in Chicago
Modern Luxe Retreat in Pilsen’s Colorful Center
2 bedrooms, 2 queen beds, 1 bath
Nov 1–6
4.98 out of 5 average rating, 51 reviews
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 queen bed, 1 bath
Sep 6–11
New place to stay
Top guest favourite
Room in Oak Forest
Cozy Cove on Chestnut
2 beds, 1 bath
Aug 29–Sep 3
4.97 out of 5 average rating, 324 reviews
Guest favourite
Apartment in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 baths
Sep 27–Oct 2
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed, 1 bath
Nov 10–15
4.96 out of 5 average rating, 320 reviews
Guest favourite
Guest suite in Chicago
Peaceful Portage Park Apartment
2 bedrooms, 2 beds, 1 bath
Nov 1–6
4.94 out of 5 average rating, 474 reviews
Top guest favourite
Apartment in Chicago
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds, 1 bath
Nov 1–6
4.99 out of 5 average rating, 137 reviews
Guest favourite
Apartment in Chicago
3 bed Bucktown Duplex, next to the 606 bike trail
3 bedrooms, 4 beds, 1 bath
Aug 28–Sep 2
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Apartment in Chicago
Modern 1 BR Near the L, Beach - Bright and Sunny!
1 bedroom, 2 beds, 1 bath
Nov 2–7
5.0 out of 5 average rating, 16 reviews
Guest favourite
Apartment in Chicago
Beautiful, sunny 2nd floor 3BR/1BA w free parking
3 bedrooms, 4 beds, 1 bath
Oct 24–29
4.92 out of 5 average rating, 171 reviews
Top guest favourite
Apartment in Chicago
Music-Inspired 2BR Garden Flat in Historic Uptown
2 bedrooms, 2 beds, 1 bath
Dec 1–6
5.0 out of 5 average rating, 22 reviews