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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in West Loop
Fulton Market Loft | Rooftop Fire Pit | Parking
3 bedrooms, 3 beds, 2.5 private bathrooms
22–27 Aug
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4.96 out of 5 average rating, 282 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 121 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.91 out of 5 average rating, 23 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
4.95 out of 5 average rating, 41 reviews, 5 bedrooms, 18 beds, 3.5 bathrooms
2–7 Aug
Guest favourite
Flat in Portage Park
NW Chicago Garden Apartment
4.92 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Guest favourite
Apartment in South Side
The Modern Woodlawn 2 Bed 2 Bath
4.96 out of 5 average rating, 81 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
Apartment in Wicker Park
Ukrainian Village 2 Bd/2ba - Steps from Division!
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Guest favourite
Flat in South Side
Modern Soul Retreat: 3BR in Bronzeville/HydePark
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Flat in Downtown Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
10–15 Aug
Home in South Side
Modern 3BR Near Obama Center, UChicago & McCormick
New place to stay, 3 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
Superhost
Flat in Chicago
Luxurious 5BD/2BA Duplex+Free Wine & Parking
New place to stay, 5 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 54 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Nov
Top guest favourite
Flat in South Side
Roomy and Comfortable Apartment with everything UN
5.0 out of 5 average rating, 31 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Guest favourite
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
4.94 out of 5 average rating, 66 reviews, 2 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 65 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
Guest favourite
Apartment in Bronzeville
Ultimate Group Experience Entire Building Chicago
4.8 out of 5 average rating, 10 reviews, 9 bedrooms, 15 beds, 6 bathrooms
20–25 Sept