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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Chicago
The Penthouse Gallery at OHC
3 bedrooms, 3 beds, 2 private bathrooms
27 Jul – 1 Aug
,
4.92 out of 5 average rating, 542 reviews
Top guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 21 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
12–17 Jul
4.98 out of 5 average rating, 85 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Chicago
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds
6–11 Jul
4.94 out of 5 average rating, 66 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms, 5 beds
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds
16–21 Aug
4.95 out of 5 average rating, 107 reviews
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
5.0 out of 5 average rating, 8 reviews
Superhost
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds
16–21 Aug
New place to stay
Luxe
Flat in Chicago
Luxury Downtown 4BR | Exclusive Design PH
4 bedrooms, 5 beds
6–11 Jul
4.98 out of 5 average rating, 40 reviews
Guest favourite
Home in Chicago
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds
15–20 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Norridge
Modern Ranch | 5 Min to O'Hare, 25 to Chicago
3 bedrooms, 3 beds
26–31 Jul
4.93 out of 5 average rating, 14 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
Apartment in Chicago
Luxury Oasis in the Heart of the City w Roof Deck
3 bedrooms, 3 beds
6–11 Jul
New place to stay
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
15–20 Aug
4.96 out of 5 average rating, 161 reviews
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 64 reviews