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Search results; Over 1,000 homes in Chicago

Top guest favourite
Bungalow in Chicago
Chicago Bootlegger House Sleeps 10-20
6 bedrooms, 10 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.96 out of 5 average rating, 158 reviews
Place to stay in Chicago
Twin Bed | Near Train Station | McCormick Pl
1 bedroom, 1 bed, 2 bathrooms
12–17 Jul
New place to stay
Guest favourite
Place to stay in Chicago
Large Brand New Room in Hyde Park Close toDowntown
1 bedroom, 1 queen bed, 1 bathroom
14–19 Oct
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Place to stay in Chicago
Spacious Sun-Lit Suite in Chicago
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Chicago
Fun & cozy getaway w/POOL/game room/FREE parking
1 bedroom, 3 queen beds, 1 bathroom
21–26 Jun
4.98 out of 5 average rating, 154 reviews
Top guest favourite
Place to stay in Berwyn
room in family home
1 bedroom, 1 bed, 1 bathroom
1–6 Dec
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 108 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed, 1 bathroom
14–19 Mar
4.96 out of 5 average rating, 309 reviews
Guest favourite
Flat in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bedroom, 1 bed, 1 bathroom
24–29 Oct
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Flat in Chicago
Historic oasis in the middle of everything.
3 bedrooms, 4 beds, 1 bathroom
21–26 Jun
4.96 out of 5 average rating, 312 reviews
Top guest favourite
Flat in Chicago
Comfortable Vintage North Side Retreat for 8
3 bedrooms, 5 beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 246 reviews
Top guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
25–30 Jun
4.96 out of 5 average rating, 101 reviews
Top guest favourite
Flat in Oak Park
Spacious & Stylish Duplex Parking & Walkability
3 bedrooms, 5 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 81 reviews
Top guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Chicago
NW Chicago Garden Apartment
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
4.92 out of 5 average rating, 49 reviews
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms, 4 beds, 3 bathrooms
5–10 Jul
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Chicago
Stylish 2BR stunner w/ unbeatable location
2 bedrooms, 3 beds, 1 bathroom
1–6 Jul
4.93 out of 5 average rating, 187 reviews
Top guest favourite
Home in Chicago
Chicago Life Apartment
3 bedrooms, 3 beds, 1 bathroom
21–26 Jun
5.0 out of 5 average rating, 47 reviews
Flat in Chicago
Chic 3BR Sun-Filled Oasis: Wicker & Logan Square
3 bedrooms, 3 beds, 1 bathroom
29 Jun – 4 Jul
New place to stay