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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Best in Chicago, private, amazing garden space
2 bedrooms, 3 beds, 1 private bathroom
9–14 Aug
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4.95 out of 5 average rating, 749 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 12 beds, 3.5 bathrooms
1–6 Jul
4.95 out of 5 average rating, 41 reviews
Superhost
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds, 1 bathroom
12–17 Jul
4.93 out of 5 average rating, 137 reviews
Flat in Chicago
Northside Chicago Apartment
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
New place to stay
Home in Chicago
Designer Home | Steps to the Obama Center & Beach
5 bedrooms, 10 beds, 3.5 bathrooms
1–6 Jul
New place to stay
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Guest favourite
Flat in Chicago
Best City Views • Rooftop Nights • EV Garage Free
2 bedrooms, 6 beds, 2 bathrooms
1–6 Jul
4.98 out of 5 average rating, 84 reviews
Top guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Chicago
Easy Downtown Access from The Pilsen Haven
3 bedrooms, 3 beds, 1 bathroom
4–9 Jul
5.0 out of 5 average rating, 26 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
New place to stay
Guest favourite
Flat in Chicago
Millennium Park 10 Min, Parking, Balcony, Sleeps 8
2 bedrooms, 4 beds, 2 bathrooms
3–8 Jul
4.97 out of 5 average rating, 158 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 21 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, 475 reviews
Superhost
Flat in Chicago
10 Min to Downtown | 3BR 2BA Spacious Home
3 bedrooms, 3 beds, 2 bathrooms
1–6 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Chicago
Bright Wrigleyville Stay | Near Transit & Parks
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.94 out of 5 average rating, 16 reviews
Guest favourite
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, 8 reviews
Flat in Berwyn
Spacious 2BD w/Game Table for 7 near City+Airport
2 bedrooms, 4 beds, 1 bathroom
21–26 Jul
New place to stay