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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Lake View
Wrigleyville/Boystown/Entire Private Floor!
1 bedroom, 3 beds, 1 private bathroom
22–27 Sept
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4.85 out of 5 average rating, 282 reviews
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
4.95 out of 5 average rating, 41 reviews, 5 bedrooms, 12 beds, 3.5 bathrooms
1–6 Jul
Superhost
Home in West Side
Beautiful Chicago Greystone
4.93 out of 5 average rating, 137 reviews, 4 bedrooms, 4 beds, 1 bathroom
12–17 Jul
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
4.97 out of 5 average rating, 76 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Jul
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
3–8 Jul
Guest favourite
Apartment in South Side
The Langley Luxe modern style unit
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Guest favourite
Apartment in West Side
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
4.88 out of 5 average rating, 475 reviews, 2 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
Home in West Town
Comfortable welcoming stay for business or leisure
New place to stay, 3 bedrooms, 4 beds, 1 bathroom
1–6 Jul
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 52 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
Top guest favourite
Flat in West Side
Easy Downtown Access from The Pilsen Haven
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 1 bathroom
4–9 Jul
Top guest favourite
Flat in South Side
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
Rooms in Chicago
Historic North Park home
4.97 out of 5 average rating, 112 reviews, 3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
Guest favourite
Home in Humboldt Park
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
Guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Home in South Side
Designer Home | Steps to the Obama Center & Beach
New place to stay, 5 bedrooms, 10 beds, 3.5 bathrooms
12–17 Jul
Home in Chicago
3BR Home Near Airport | Patio | Free Parking
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 1 bathroom
1–6 Jul
Flat in West Rogers Park
Northside Chicago Apartment
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
New place to stay, 5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug