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Search results; Over 1,000 homes in Chicago

Top guest favourite
Home in Chicago
The Grand Kimball Lodge, Logan Square, Sleeps 15
4 bedrooms, 10 beds, 3 private bathrooms
30 Sept – 5 Oct
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4.96 out of 5 average rating, 173 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
16–21 Jul
4.97 out of 5 average rating, 93 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
20–25 Sept
4.95 out of 5 average rating, 22 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
12–17 Oct
4.95 out of 5 average rating, 121 reviews
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
2 bedrooms, 3 beds
6–11 Aug
New place to stay
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
6–11 Dec
4.99 out of 5 average rating, 108 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
23–28 Aug
4.92 out of 5 average rating, 13 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 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, 20 reviews
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
2 bedrooms, 2 queen beds
22–27 Aug
New place to stay
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, 12 reviews
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds
16–21 Aug
4.88 out of 5 average rating, 434 reviews
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds
9–14 Aug
5.0 out of 5 average rating, 10 reviews
Place to stay in Chicago
Guest room in Dunning, Chicago IL
1 bedroom, 1 queen bed
19–24 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Chic 3BR Sun-Filled Oasis: Wicker & Logan Square
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Brookfield
Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
4 bedrooms, 4 beds
26–31 Jul
4.94 out of 5 average rating, 16 reviews
Guest favourite
Flat in Chicago
Luxury Designer Loft 302 | River North
3 bedrooms, 3 queen beds
9–14 Aug
4.89 out of 5 average rating, 9 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms
20–25 Sept
4.95 out of 5 average rating, 19 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, 81 reviews