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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
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, 13 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, 7 reviews
Flat in Chicago
3BR Vintage Apt • Patio • Walk to McKinley Park
3 bedrooms, 3 queen beds, 1 bathroom
21–26 Jun
New place to stay
Superhost
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
24–29 Jun
4.98 out of 5 average rating, 59 reviews
Flat in Chicago
Garden Retreat Pilsen Chicago Apartment
2 bedrooms, 3 beds, 2 bathrooms
29 Jun – 4 Jul
5.0 out of 5 average rating, 4 reviews
Flat in Chicago
Retro Logan Square Retreat • Blue Line
1 bedroom, 1 bunk bed, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 3 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, 15 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
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
New place to stay
Superhost
Flat in Chicago
Stunning Apt, walk to NEU, “The Bernard”
4 bedrooms, 3 beds, 1 bathroom
26–31 Jul
Guest favourite
Room in Chicago
Private Room in Norwood Park
1 bed, 1 bathroom
28 Jun – 3 Jul
4.97 out of 5 average rating, 38 reviews
Home in Chicago
Steps to Lake & Beach! Multi-Level Oakland Haven
4 bedrooms, 5 beds, 4.5 bathrooms
29 Jun – 4 Jul
New place to stay
Flat in Chicago
Luxury South Loop Apt
2 beds, 1 bathroom
2–7 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
9–14 Aug
4.97 out of 5 average rating, 62 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
Guest favourite
Flat in Evanston
"Melody of Evanston 3bd, 2 Bath UrbanLux"
3 bedrooms, 6 beds, 2 bathrooms
20–25 Jun
4.94 out of 5 average rating, 36 reviews
Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
5–10 Jul
4.93 out of 5 average rating, 230 reviews