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Search results; Over 1,000 homes in Chicago

Guest favourite
Guest suite in Chicago
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
LIVN Millennium Park Downtown Chicago 1 BR
4.97 out of 5 average rating, 79 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Jul
Superhost
Home in Chicago
Cozy Luxury Escape Amazing location private home
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Jul
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
5.0 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Home in Chicago
Comfortable welcoming stay for business or leisure
New place to stay, 3 bedrooms, 4 beds, 1 bathroom
3–8 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
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
Guest favourite
Flat in Chicago
Luxury Loft Collection 03 - Terrace - River North
4.95 out of 5 average rating, 107 reviews, 3 bedrooms, 7 beds, 3 bathrooms
16–21 Aug
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
Home in Chicago
Modern 3BR Near Obama Center, UChicago & McCormick
New place to stay, 3 bedrooms, 3 beds, 1 bathroom
14–19 Jul
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
4.95 out of 5 average rating, 41 reviews, 5 bedrooms, 17 beds, 3.5 bathrooms
3–8 Jul
Guest favourite
Flat in Evanston
NEW Fam-Frndly 3 bd 1 bth w/ EZ Parking near NU
4.94 out of 5 average rating, 163 reviews, 3 bedrooms, 1 bathroom
24–29 Jul
Guest favourite
Apartment in Chicago
12 Min Downtown, Free Parking, Rooftop, Sleeps 11
4.91 out of 5 average rating, 32 reviews, 2 bedrooms, 8 beds, 2 bathrooms
5–10 Jul
Luxe
Flat in Chicago
Luxury Downtown 4BR | Exclusive Design PH
4.97 out of 5 average rating, 39 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
3–8 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
Top guest favourite
Flat in Chicago
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
4.98 out of 5 average rating, 129 reviews, 2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
Top guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
4.9 out of 5 average rating, 39 reviews, 5 bedrooms, 5 beds, 2 bathrooms
16–21 Aug