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Search results; Over 1,000 homes in Chicago

Guest favourite
Guest suite in Chicago
Cozy Home Living, Dogs, Kids, Free Parking, 420 OK
3 bedrooms, 4 beds, 1 private bathroom
7–12 Sept
,
4.94 out of 5 average rating, 196 reviews
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, 26 reviews
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds
8–13 Aug
New place to stay
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 117 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
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
9–14 Aug
4.95 out of 5 average rating, 84 reviews
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
21–26 Aug
New place to stay
Top guest favourite
Home in Chicago
Big house in the BEST Location!
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
9–14 Nov
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
15–20 Nov
5.0 out of 5 average rating, 56 reviews
Flat in Skokie
Skokie Serenity - 3 queen beds
3 bedrooms, 3 queen beds
17–22 Sept
4.67 out of 5 average rating, 3 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 126 reviews
Flat in Chicago
Apartment near McCormick w/ gym & workspace
1 bedroom, 2 beds
15–20 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds
25–30 Oct
4.94 out of 5 average rating, 252 reviews
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds
30 Aug – 4 Sept
4.88 out of 5 average rating, 437 reviews
Top guest favourite
Room in Chicago
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
3 beds
27 Nov – 2 Dec
4.95 out of 5 average rating, 685 reviews
Top guest favourite
Flat in Chicago
Cozy & Spacious Sunny 2 bedroom apartment.
2 bedrooms, 2 beds
19–24 Oct
4.98 out of 5 average rating, 108 reviews
Guest favourite
Room in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bed
24–29 Oct
4.9 out of 5 average rating, 49 reviews
Guest favourite
Home in Chicago
Charming 3-BED in Lincoln Park/ Old Town & Parking
3 bedrooms, 3 beds
4–9 Oct
4.95 out of 5 average rating, 187 reviews