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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
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 62 reviews
Flat in Berwyn
Spacious 2BD w/Game Table for 7 near City+Airport
2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
New place to stay
Home in Chicago
Newly Renovated Home 4BD/3BTH with garage!
4 bedrooms, 5 beds, 3 bathrooms
4–9 Aug
New place to stay
Guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Apartment in Chicago
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.88 out of 5 average rating, 473 reviews
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 13 reviews
Flat in Chicago
Chic 3BR Sun-Filled Oasis: Wicker & Logan Square
3 bedrooms, 3 beds, 1 bathroom
12–17 Jul
New place to stay
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, 109 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
2–7 Aug
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
23–28 Oct
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
3–8 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Oak Park
Spacious & Stylish Duplex Prime Location & Parking
3 bedrooms, 5 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 81 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
8–13 Jul
4.96 out of 5 average rating, 101 reviews
Guest favourite
Place to stay in Chicago
The Native Garden at the City's Edge
1 bedroom, 1 queen bed, 1 bathroom
4–9 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Room in Des Plains
Peaceful Vintage Charm Retreat Min.from O'Hare
1 bed, 1 bathroom
4–9 Jul
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
6–11 Dec
4.99 out of 5 average rating, 107 reviews