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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Chicago
Peaceful River West, free parking
2 bedrooms, 2 beds, 1 private bathroom
5–10 Aug
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4.97 out of 5 average rating, 454 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.92 out of 5 average rating, 26 reviews, 4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
New place to stay, 4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Aug
Top guest favourite
Rooms in Chicago
Historic North Park home
4.97 out of 5 average rating, 117 reviews, 3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
4.95 out of 5 average rating, 84 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Room in Chicago
Spacious garden level suite
4.96 out of 5 average rating, 317 reviews, 1 queen bed, 1 bathroom
10–15 Nov
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 126 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Home in Chicago
Big house in the BEST Location!
4.98 out of 5 average rating, 62 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
Flat in Chicago
Duplex in Bucktown
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
4.99 out of 5 average rating, 108 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Nov
Top guest favourite
Guest house in Chicago
Pilsen Gem Near the Loop & Chinatown
5.0 out of 5 average rating, 20 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 56 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Nov
Flat in Skokie
Skokie Serenity - 3 queen beds
4.67 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
15–20 Aug
Top guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
4.94 out of 5 average rating, 252 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
New place to stay, 3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Flat in Chicago
Apartment near McCormick w/ gym & workspace
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 Aug
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
4.96 out of 5 average rating, 305 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
Guest favourite
Room in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
4.9 out of 5 average rating, 49 reviews, 1 bed, 1 bathroom
24–29 Oct