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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
The South Loop Reserve I Sleep 6 I Top Rated
2 bedrooms, 2 beds, 2 private bathrooms
3–9 Aug
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4.93 out of 5 average rating, 258 reviews
Flat in Chicago
Northside Chicago Apartment
2 bedrooms, 2 beds
7–12 Sept
New place to stay
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
3–8 Jul
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds
12–17 Jul
4.93 out of 5 average rating, 137 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 12 beds
1–6 Jul
4.95 out of 5 average rating, 41 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
9–14 Aug
New place to stay
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
16–21 Aug
4.96 out of 5 average rating, 80 reviews
Guest favourite
Home in Norridge
Modern Ranch | 5 Min to O'Hare, 25 to Chicago
3 bedrooms, 3 beds
18–23 Jul
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 21 reviews
Superhost
Flat in Chicago
Cozy Urban View Retreat Near Downtown - Sleeps 7
2 bedrooms, 4 beds
10–15 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Evanston
NEW Fam-Frndly 3 bd 1 bth w/ EZ Parking near NU
3 bedrooms
3–8 Jul
4.94 out of 5 average rating, 163 reviews
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
23–28 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms, 4 beds
5–10 Jul
4.91 out of 5 average rating, 188 reviews
Guest favourite
Place to stay in Chicago
Large Brand New Room in Hyde Park Close toDowntown
1 bedroom, 1 queen bed
23–28 Oct
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Chicago
Easy Downtown Access from The Pilsen Haven
3 bedrooms, 3 beds
4–9 Jul
5.0 out of 5 average rating, 26 reviews
Guest favourite
Apartment in Chicago
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds
5–10 Jul
4.88 out of 5 average rating, 474 reviews