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Search results; Over 1,000 homes in Chicago

Superhost
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds, 1 private bathroom
7–12 Sept
,
4.94 out of 5 average rating, 140 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 12 beds
2–7 Jul
4.95 out of 5 average rating, 41 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
9–14 Aug
New place to stay
Flat in Berwyn
Spacious 2BD w/Game Table for 7 near City+Airport
2 bedrooms, 4 beds
21–26 Jul
New place to stay
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
4–9 Jul
4.97 out of 5 average rating, 77 reviews
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms, 3 beds
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
5–10 Jul
5.0 out of 5 average rating, 52 reviews
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Home in Chicago
Blonde Beauty Cozy Home Near Downtown Attractions
4 bedrooms, 4 beds
12–17 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Easy Downtown Access from The Pilsen Haven
3 bedrooms, 3 beds
21–26 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds
5–10 Jul
4.93 out of 5 average rating, 337 reviews
Top guest favourite
Flat in Chicago
The Nest | Luxe Garden Unit Near Downtown
2 bedrooms, 2 beds
5–10 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds
5–10 Jul
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds
5–10 Jul
5.0 out of 5 average rating, 6 reviews
Flat in Chicago
Northside Chicago Apartment
2 bedrooms, 2 beds
7–12 Sept
New place to stay
Superhost
Flat in Chicago
Paradise Lounge South loop 3br W/ Balcony
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Chicago
NW Chicago Garden Apartment
2 bedrooms, 2 beds
8–13 Sept
4.92 out of 5 average rating, 51 reviews