filters

Search results; Over 1,000 homes in Chicago

Descriptions are based on details hosts provide
Top guest favourite
Apartment in Chicago
Private rooftop | Breathtaking skyline view
2 bedrooms, 3 beds, 2 private bathrooms
10–15 Aug
,
5.0 out of 5 average rating, 60 reviews
Guest favourite
Home in Chicago
Spa tub and a private backyard fireplace
4.91 out of 5 average rating, 23 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.97 out of 5 average rating, 93 reviews, 1 bedroom, 1 bed, 1 bathroom
22–27 Jul
Home in Franklin Park
Newly remodeled with backyard and gazebo
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 1 bathroom
22–27 Aug
Flat in Skokie
Skokie Serenity - 3 queen beds
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Brookfield
Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
4.94 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Flat in Chicago
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
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 121 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
Top guest favourite
Rooms in Chicago
Historic North Park home
4.97 out of 5 average rating, 113 reviews, 3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
4.93 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Superhost
Home in Chicago
Renovated Mayfair retreat with a fire pit
6 bedrooms, 11 beds, 3 bathrooms
26–31 Jul
Place to stay in Chicago
Central spot near downtown with workspace
New place to stay, 1 bedroom, 1 bed, 2 bathrooms
13–18 Aug
Guest favourite
Place to stay in Chicago
x3 Private room with bath Hyde Park UChicago
5.0 out of 5 average rating, 16 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Aug
Top guest favourite
Room in Chicago
Near UofC with patio and free parking
4.93 out of 5 average rating, 182 reviews, 1 double bed, 1 bathroom
7–12 Sept
Place to stay in Chicago
Near McCormick Place and train station
New place to stay, 1 bedroom, 1 bed, 2 bathrooms
4–9 Aug
Guest favourite
Apartment in Chicago
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
Top guest favourite
Flat in Chicago
Sun filled tranquil 2 br great part of Logan Sq.
4.77 out of 5 average rating, 569 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Chicago
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
Flat in Chicago
Rooftop city views near McCormick Place
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 2 beds, 1 bathroom
3–8 Aug