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Search results; Over 1,000 homes in Chicago

Guest favourite
Guest suite in Portage Park
Tropical Bungalow Getaway in Quiet Neighborhood
1 bedroom, 2 beds, 1 private bathroom
4–9 Aug
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4.89 out of 5 average rating, 116 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
4–9 Jul
4.98 out of 5 average rating, 80 reviews
Superhost
Home in Ukrainian Village
Cozy Luxury Escape Amazing location private home
3 bedrooms, 3 beds
3–8 Jul
New place to stay
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
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Superhost
Flat in West Side
10 Min to Downtown | 3BR 2BA Spacious Home
3 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 3 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
Flat in Wicker Park
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds
16–21 Aug
4.95 out of 5 average rating, 107 reviews
Top guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 17 reviews
Home in West Town
Comfortable welcoming stay for business or leisure
3 bedrooms, 4 beds
3–8 Jul
New place to stay
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 17 beds
3–8 Jul
4.95 out of 5 average rating, 41 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, 7 reviews
Luxe
Flat in Chicago Loop
Luxury Downtown 4BR | Exclusive Design PH
4 bedrooms, 5 beds
3–8 Jul
4.97 out of 5 average rating, 39 reviews
Home in South Side
Modern 3BR Near Obama Center, UChicago & McCormick
3 bedrooms, 3 queen beds
14–19 Jul
New place to stay
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, 7 reviews
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
9–14 Aug
New place to stay
Top guest favourite
Flat in Lake View
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds
5–10 Jul
4.99 out of 5 average rating, 346 reviews