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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Chicago
Edgewater escape, charming 2 BR, Rooftop Solar
2 bedrooms, 2 beds, 1 private bathroom
23–28 Aug
,
4.89 out of 5 average rating, 387 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
27 Jan – 1 Feb
5.0 out of 5 average rating, 38 reviews
Flat in Skokie
Skokie Serenity - 3 queen beds
3 bedrooms, 3 queen beds
17–22 Sept
New place to stay
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
4–9 Oct
4.92 out of 5 average rating, 25 reviews
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds
8–13 Aug
New place to stay
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds
16–21 Aug
New place to stay
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
3–8 Dec
4.99 out of 5 average rating, 108 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, 305 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed
10–15 Nov
4.96 out of 5 average rating, 317 reviews
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds
16–21 Aug
4.93 out of 5 average rating, 342 reviews
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
28 Sept – 3 Oct
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
15–20 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms
20–25 Sept
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
21–26 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Chicago
Fulton House #1 (2bd/ 1ba)
2 bedrooms, 2 queen beds
2–7 Aug
4.95 out of 5 average rating, 111 reviews
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
30 Aug – 4 Sept
4.98 out of 5 average rating, 162 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
21–26 Sept
4.96 out of 5 average rating, 68 reviews
Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds
15–20 Aug
4.91 out of 5 average rating, 111 reviews