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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Chicago
The Upscale Getaway Near Downtown
2 bedrooms, 3 beds, 2 private bathrooms
12–17 Aug
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4.93 out of 5 average rating, 291 reviews
Top guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
24–29 Jun
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Oct
4.95 out of 5 average rating, 115 reviews
Flat in Chicago
Retro Logan Square Retreat • Blue Line
1 bedroom, 1 bunk bed
22–27 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms, 4 beds
5–10 Jul
5.0 out of 5 average rating, 14 reviews
Home in Chicago
The Dorchester | Steps to the Obama Center & Beach
5 bedrooms, 10 beds
27 Jun – 2 Jul
New place to stay
Top guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds
25–30 Jun
4.96 out of 5 average rating, 101 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
Place to stay in Chicago
The Native Garden at the City's Edge
1 bedroom, 1 queen bed
4–9 Aug
5.0 out of 5 average rating, 6 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
Flat in Chicago
Bright 1BR unit w/ elevator & Wifi
1 bedroom, 1 queen bed
5–10 Jul
5.0 out of 5 average rating, 6 reviews
Superhost
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
27 Jun – 2 Jul
4.96 out of 5 average rating, 156 reviews
Superhost
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds
19–24 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest house in Chicago
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds
28 Jun – 3 Jul
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Chicago
Boho City Escape | Parking + Balcony
2 bedrooms, 3 beds
3–8 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Apartment in Chicago
Stylish Chicago Firefighter 3 bed Retreat-Sleeps 7
3 bedrooms, 4 beds
23–28 Aug
4.97 out of 5 average rating, 75 reviews
Flat in Chicago
Luxury South Loop Apt
2 beds
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Chicago
Wrigleyville Inn. Historic Greystone, Free Parking
3 bedrooms, 3 queen beds
4–9 Oct
4.99 out of 5 average rating, 114 reviews
Guest favourite
Flat in Lockport
Bright Lockport Farmhouse: King Bed + Yard View
1 bedroom, 1 bed
20–25 Jun
4.98 out of 5 average rating, 43 reviews