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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Fulton Market Loft | Rooftop Fire Pit | Parking
3 bedrooms, 3 beds, 2.5 private bathrooms
18–23 Jul
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4.96 out of 5 average rating, 280 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
4.95 out of 5 average rating, 41 reviews, 5 bedrooms, 12 beds, 3.5 bathrooms
2–7 Jul
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Superhost
Home in Chicago
Beautiful Chicago Greystone
4.94 out of 5 average rating, 140 reviews, 4 bedrooms, 4 beds, 1 bathroom
12–17 Jul
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
New place to stay, 5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.97 out of 5 average rating, 77 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Jul
Guest favourite
Flat in Chicago
Modern 6BR Suite with Pool-table near McCormick
4.96 out of 5 average rating, 27 reviews, 6 bedrooms, 6 beds, 2 bathrooms
6–11 Jul
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Home in Chicago
Blonde Beauty Cozy Home Near Downtown Attractions
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
Flat in Berwyn
Spacious 2BD w/Game Table for 7 near City+Airport
New place to stay, 2 bedrooms, 4 beds, 1 bathroom
21–26 Jul
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
4.93 out of 5 average rating, 337 reviews, 2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
Top guest favourite
Flat in Chicago
Easy Downtown Access from The Pilsen Haven
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 1 bathroom
21–26 Jul
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
Home in Chicago
3BR Home Near Airport | Patio | Free Parking
4.5 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Jul
Guest favourite
Flat in Chicago
PerfectChicagoStay/3Bedrooms/NearTrain&Dowtown
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 4 beds, 1 bathroom
2–7 Jul
Guest favourite
Flat in Chicago
NW Chicago Garden Apartment
4.92 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept