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Search results; Over 1,000 homes in Chicago

Top guest favourite
Home in Logan Square
The Grand Kimball Lodge, Logan Square, Sleeps 15
4 bedrooms, 10 beds, 3 private bathrooms
30 Sept – 5 Oct
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4.96 out of 5 average rating, 173 reviews
Guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 117 reviews
Home in Belmont Cragin
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Aug
New place to stay
Guest favourite
Apartment in South Side
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
4.95 out of 5 average rating, 84 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.93 out of 5 average rating, 107 reviews
Guest favourite
Room in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bed, 1 bathroom
9–14 Aug
4.9 out of 5 average rating, 49 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 56 reviews
Flat in Logan Square
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
New place to stay
Top guest favourite
Home in Chicago
Big house in the BEST Location!
3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 62 reviews
Guest favourite
Flat in South Side
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Ukrainian Village
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 252 reviews
Top guest favourite
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in West Rogers Park
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
3–8 Dec
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Room in Roscoe Village
Spacious garden level suite
1 queen bed, 1 bathroom
10–15 Nov
4.96 out of 5 average rating, 317 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
19–24 Dec
4.95 out of 5 average rating, 126 reviews
Flat in South Side
Apartment near McCormick w/ gym & workspace
1 bedroom, 2 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
29 Aug – 3 Sept
4.96 out of 5 average rating, 305 reviews
Top guest favourite
Flat in Lake View
An elegant Chicago Northside Getaway
3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 374 reviews