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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
Guest favourite
Flat in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bedroom, 1 bed
24–29 Oct
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Place to stay in Chicago
Spacious Sun-Lit Suite in Chicago
2 bedrooms, 2 beds
9–14 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Chicago
Historic oasis in the middle of everything.
3 bedrooms, 4 beds
21–26 Jun
4.96 out of 5 average rating, 312 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed
14–19 Mar
4.96 out of 5 average rating, 309 reviews
Guest favourite
Rooms in Chicago
Spacious Haven in North Park
3 bedrooms, 4 beds
21–26 Sept
4.9 out of 5 average rating, 61 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, 108 reviews
Top guest favourite
Flat in Chicago
Fun & cozy getaway w/POOL/game room/FREE parking
1 bedroom, 3 queen beds
21–26 Jun
4.98 out of 5 average rating, 155 reviews
Top guest favourite
Place to stay in Berwyn
room in family home
1 bedroom, 1 bed
1–6 Dec
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Chicago
Comfortable Vintage North Side Retreat for 8
3 bedrooms, 5 beds
23–28 Aug
4.92 out of 5 average rating, 246 reviews
Home in Chicago
The Dorchester | Steps to the Obama Center & Beach
5 bedrooms, 10 beds
27 Jun – 2 Jul
New place to stay
Flat in Chicago
Lake Shore Condo | Beach | North Chicago
2 bedrooms, 2 beds
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
14–19 Oct
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Oak Park
Spacious & Stylish Duplex Parking & Walkability
3 bedrooms, 5 beds
17–22 Aug
5.0 out of 5 average rating, 81 reviews
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
9–14 Aug
4.97 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Chicago
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds
23–28 Aug
4.95 out of 5 average rating, 258 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
16–21 Aug
4.96 out of 5 average rating, 79 reviews
Guest favourite
Room in Chicago
Accommodation for 2 people (basement)
1 queen bed
21–26 Jun
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Chicago
NW Chicago Garden Apartment
2 bedrooms, 2 beds
8–13 Sept
4.92 out of 5 average rating, 49 reviews