filters

Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Downtown Chicago
Urban Chic Apartment by the Magnificent Mile
2 bedrooms, 2 beds, 1 private bathroom
26–31 Oct
,
4.94 out of 5 average rating, 290 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
7–12 Jul
4.98 out of 5 average rating, 82 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
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
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
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
9–14 Aug
New place to stay
Apartment in Wicker Park
Luxury Oasis in the Heart of the City w Roof Deck
3 bedrooms, 3 beds
5–10 Jul
New place to stay
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 64 reviews
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms, 5 beds
10–15 Aug
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
Guest favourite
Apartment in West Side
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds
16–21 Aug
4.88 out of 5 average rating, 476 reviews
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
Top guest favourite
Flat in Bridgeport
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds
21–26 Sept
4.98 out of 5 average rating, 129 reviews
Luxe
Flat in Chicago Loop
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 Ukrainian Village
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds
15–20 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Apartment in Wrigleyville
Wrigleyville Updated Condo with Free Parking
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 101 reviews
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
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