filters

Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Ravenswood
Private Lincoln Square one bed+bath studio apt.
1 bedroom, 1 bed, 1 private bathroom
1–6 Nov
,
4.99 out of 5 average rating, 427 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
15–20 Jul
4.98 out of 5 average rating, 87 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Bridgeport
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 233 reviews
Top guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Jefferson Park
Lovely 6 Bd Retreat w/ Game Room, Back Deck & Bar
6 bedrooms, 9 beds, 3 bathrooms
12–17 Jul
4.98 out of 5 average rating, 81 reviews
Top guest favourite
Room in Irving Park
Cozy Room for One In The Company of Cats -Blueline
1 single bed, 1 bathroom
19–24 Sept
4.94 out of 5 average rating, 141 reviews
Top guest favourite
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 19 reviews
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 65 reviews
Luxe
Flat in Chicago Loop
Luxury Downtown 4BR | Exclusive Design PH
4 bedrooms, 5 beds, 3.5 bathrooms
8–13 Jul
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Top guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Apartment in South Side
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
4.96 out of 5 average rating, 81 reviews
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Room in Roscoe Village
Spacious garden level suite
1 queen bed, 1 bathroom
5–10 Nov
4.96 out of 5 average rating, 312 reviews
Top guest favourite
Flat in Lake View
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 348 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Flat in Ukrainian Village
iKlektik House Chicago/Cardinal
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.91 out of 5 average rating, 488 reviews