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Search results; Over 1,000 homes in Chicago

Top guest favourite
Home in Chicago
Spacious 3 Level Home with 5 BDR/3 BA & 2 Kitchens
5 bedrooms, 5 beds, 3 private bathrooms
9–14 Sept
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4.98 out of 5 average rating, 94 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
Top guest favourite
Flat in Forest Park
Sunny 1 bedroom apartment 1 block from restaurants
1 bedroom, 1 queen bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 224 reviews
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds
25–30 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Guest house in Chicago
Horner Park Coach House
1 bedroom, 1 bed
27 Oct – 1 Nov
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Apartment in Chicago
Great location. Free parking.
1 bedroom, 1 queen bed
8–13 Nov
4.97 out of 5 average rating, 919 reviews
Top guest favourite
Room in Chicago
The Native Garden at the City's Edge
1 queen bed
1–6 Nov
5.0 out of 5 average rating, 24 reviews
Guest favourite
Flat in Chicago
Guest Favorite Newly Renovated 1BR Near Lakeview
1 bedroom, 1 queen bed
22–27 Sept
4.95 out of 5 average rating, 96 reviews
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
2–7 Nov
4.95 out of 5 average rating, 170 reviews
Top guest favourite
Room in Chicago
En Suite Private Queen Bedroom/Bathroom
1 queen bed
21–26 Sept
4.88 out of 5 average rating, 272 reviews
Guest favourite
Room in Glenview
Northside home near O’hare &Downtown
2 beds
20–25 Sept
4.95 out of 5 average rating, 64 reviews
Place to stay in Chicago
#7 Historic Chicago Home - Bunk Bedroom(Twin&Full)
1 bedroom, 1 bunk bed
15–20 Nov
4.81 out of 5 average rating, 180 reviews
Top guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds
28 Sept – 3 Oct
4.93 out of 5 average rating, 243 reviews
Top guest favourite
Flat in Forest Park
Cheerful Remodel Prime Location
1 bedroom, 1 queen bed
1–6 Nov
4.92 out of 5 average rating, 151 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 122 reviews
Top guest favourite
Flat in Chicago
Your Logan Square Oasis with Lush Outdoor Haven!
2 bedrooms, 2 king beds
1–6 Nov
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Guest house in Chicago
Cozy Coach House
1 queen bed
6–11 Sept
4.96 out of 5 average rating, 509 reviews
Top guest favourite
Home in Chicago
Explore Chicago • Private Parking • Museum Access
2 bedrooms, 4 beds
28 Sept – 3 Oct
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Oak Park
Big & Bright Treetop Oasis Near Downtown w/Parking
2 bedrooms, 4 beds
1–6 Nov
4.98 out of 5 average rating, 96 reviews