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Search results; Over 1,000 homes in Chicago

Superhost
Flat in Chicago Loop
Spectacular 2BR Penthouse in the Loop | Roof Deck
2 bedrooms, 3 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.82 out of 5 average rating, 348 reviews
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
Home in South Side
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
Apartment in South Side
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
Home in Bridgeport
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
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
Top guest favourite
Flat in Ukrainian Village
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
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
Top guest favourite
Room in Roscoe Village
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 South Side
Modern Soul Retreat: 3BR in Bronzeville/HydePark
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
4.95 out of 5 average rating, 104 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Flat in West Town
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 West Rogers Park
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
3–8 Dec
Top guest favourite
Flat in Edgewater
Modern 1 BR Near the L, Beach - Bright and Sunny!
5.0 out of 5 average rating, 15 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Nov
Flat in South Side
Apartment near McCormick w/ gym & workspace
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 Aug
Guest favourite
Home in Lincoln Park
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
Flat in Downtown Chicago
Kasa Lake Shore Chicago | Studio Queen
New place to stay, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Room in Belmont Cragin
Private RM 1st FLR BDRM|12”Memory Queen BD|TV|Fan
4.94 out of 5 average rating, 51 reviews, 1 queen bed, 1.5 bathrooms
28 Sept – 3 Oct
Home in Belmont Cragin
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
New place to stay, 4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Aug