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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest house in Chicago
The Roscoe Village Guesthouse
2 bedrooms, 2 beds, 1 private bathroom
2–7 Aug
,
4.91 out of 5 average rating, 205 reviews
Top guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
20–25 Sept
4.95 out of 5 average rating, 22 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Place to stay in Chicago
Guest room in Dunning, Chicago IL
1 bedroom, 1 queen bed
31 Aug – 5 Sept
New place to stay
Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds
12–17 Jul
4.91 out of 5 average rating, 106 reviews
Home in Franklin Park
Full, fun cozy house!
2 bedrooms, 4 beds
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Place to stay in Chicago
Woodlawn Beauty: Room 2
3 bedrooms, 3 queen beds
3–8 Aug
4.5 out of 5 average rating, 6 reviews
Guest favourite
Place to stay in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bedroom, 1 bed
2–7 Aug
4.89 out of 5 average rating, 46 reviews
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed
5–10 Nov
4.96 out of 5 average rating, 313 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
15–20 Jul
4.98 out of 5 average rating, 87 reviews
Guest favourite
Flat in Chicago
Modern 3BR Apartment Near North Ave Shops
3 bedrooms, 3 double beds
21–26 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
12–17 Oct
4.95 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Flat in Chicago
2BR/1BA Apt w/ Modern Amenities Rogers Park
2 bedrooms, 2 queen beds
26–31 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 54 reviews