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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Private Lincoln Square one bed+bath studio apt.
1 bedroom, 1 bed, 1 private bathroom
1–6 Nov
,
4.99 out of 5 average rating, 427 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.98 out of 5 average rating, 87 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
4.94 out of 5 average rating, 141 reviews, 1 single bed, 1 bathroom
19–24 Sept
Superhost
Place to stay in Chicago
Woodlawn Beauty: Room 2
4.4 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
4.96 out of 5 average rating, 81 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
5.0 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Room in Chicago
Comfortable bed with Smart stand
5.0 out of 5 average rating, 5 reviews, 1 queen bed, 1 bathroom
18–23 Jul
Flat in Chicago
2BR/1BA Apt w/ Modern Amenities Rogers Park
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Home in Franklin Park
Full, fun cozy house!
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Top guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
4.93 out of 5 average rating, 233 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Superhost
Flat in Chicago
Modern 4BR West Town Duplex | Best for LongStays
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
13–18 Jul
Top guest favourite
Rooms in Chicago
Historic North Park home
4.97 out of 5 average rating, 113 reviews, 3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
Guest favourite
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 3 bathrooms
10–15 Aug
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
Guest favourite
Shipping container in Evanston
Container home. Walk to NWU and Central Street.
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul