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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Secret Garden @ The Noble Farmhouse | Wicker Park
Studio, 2 beds, 1 private bathroom
26 Sept – 1 Oct
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4.96 out of 5 average rating, 394 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
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.93 out of 5 average rating, 106 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
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
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
26–31 Dec
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
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
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
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
Flat in Skokie
Skokie Serenity - 3 queen beds
4.67 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
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
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
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
Home in Chicago
Charming 3-BED in Lincoln Park/ Old Town & Parking
4.95 out of 5 average rating, 187 reviews, 3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
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
Top guest favourite
Flat in Chicago
Cozy & Spacious Sunny 2 bedroom apartment.
4.98 out of 5 average rating, 108 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Oct
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
Flat in Chicago
Fulton House #1 (2bd/ 1ba)
4.95 out of 5 average rating, 112 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
4.95 out of 5 average rating, 21 reviews, 2 bedrooms, 2 bathrooms
20–25 Sept