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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Secret Garden @ The Noble Farmhouse | Wicker Park
Studio, 2 beds, 1 private bathroom
29 Aug – 3 Sept
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4.96 out of 5 average rating, 390 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
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
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
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
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
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
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
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
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
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
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
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
Place to stay in Chicago
Twin Bed | Near Train Station | McCormick Pl
New place to stay, 1 bedroom, 1 bed, 2 bathrooms
4–9 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
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug