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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Portage Park
Eddy Street Upstairs Apartment
1 bedroom, 1 bed, 1 shared bathroom
8–13 Sept
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4.95 out of 5 average rating, 169 reviews
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 12 beds
1–6 Jul
4.95 out of 5 average rating, 41 reviews
Superhost
Home in West Side
Beautiful Chicago Greystone
4 bedrooms, 4 beds
12–17 Jul
4.93 out of 5 average rating, 137 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
1–6 Jul
4.97 out of 5 average rating, 76 reviews
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
3–8 Jul
5.0 out of 5 average rating, 12 reviews
Guest favourite
Apartment in South Side
The Langley Luxe modern style unit
2 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Apartment in West Side
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds
5–10 Jul
4.88 out of 5 average rating, 475 reviews
Home in West Town
Comfortable welcoming stay for business or leisure
3 bedrooms, 4 beds
1–6 Jul
New place to stay
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
5–10 Jul
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Flat in West Side
Easy Downtown Access from The Pilsen Haven
3 bedrooms, 3 beds
4–9 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Flat in South Side
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 Humboldt Park
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds
5–10 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
5.0 out of 5 average rating, 6 reviews
Home in South Side
Designer Home | Steps to the Obama Center & Beach
5 bedrooms, 10 beds
12–17 Jul
New place to stay
Home in Chicago
3BR Home Near Airport | Patio | Free Parking
3 bedrooms, 3 queen beds
1–6 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in North Side
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds
5–10 Jul
4.93 out of 5 average rating, 337 reviews
Flat in West Rogers Park
Northside Chicago Apartment
2 bedrooms, 2 beds
7–12 Sept
New place to stay
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
9–14 Aug
New place to stay