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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
18–23 Oct
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4.96 out of 5 average rating, 176 reviews
Guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds
1–6 Nov
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Apartment in Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds
1–6 Nov
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 60 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 62 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 34 reviews
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 15 reviews
Guest favourite
Flat in Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds
3–8 Nov
4.95 out of 5 average rating, 111 reviews
Top guest favourite
Apartment in Chicago
Private rooftop | Breathtaking skyline view
2 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 68 reviews
Top guest favourite
Guest house in Chicago
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 queen beds
6–11 Dec
4.99 out of 5 average rating, 962 reviews
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
15–20 Nov
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Flat in Oak Park
Space & Style Near Downtown Parking+Walk To It All
3 bedrooms, 5 beds
11–16 Nov
5.0 out of 5 average rating, 101 reviews
Top guest favourite
Flat in Chicago
Modern & Spacious Condo Minutes from the Loop
3 bedrooms, 3 queen beds
28 Nov – 3 Dec
4.97 out of 5 average rating, 95 reviews
Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 361 reviews
Top guest favourite
Apartment in Chicago
Great location. Free parking.
1 bedroom, 1 queen bed
29 Nov – 4 Dec
4.97 out of 5 average rating, 925 reviews
Guest favourite
Flat in Chicago
Gold Coast Luxury: 2BR with Sweeping City Vistas
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 126 reviews
Guest favourite
Flat in Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds
25–30 Oct
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
25–30 Oct
4.98 out of 5 average rating, 170 reviews