filters

Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
11–16 Jan
4.95 out of 5 average rating, 132 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
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
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
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
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
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
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, 41 reviews
Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 109 reviews
Top guest favourite
Flat in Chicago
Coach House in Historic Old Town Chicago
1 bedroom, 2 beds
26–31 Oct
4.96 out of 5 average rating, 143 reviews
Guest favourite
Flat in Chicago
Spacious & New Industrial Condo Close to Downtown
3 bedrooms, 4 queen beds
4–9 Oct
4.9 out of 5 average rating, 302 reviews
Top guest favourite
Flat in Chicago
Chic retreat near the best of Lakeview & Wrigley
1 bedroom, 1 queen bed
25–30 Oct
4.93 out of 5 average rating, 195 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, 125 reviews
Top guest favourite
Flat in Chicago
Chic & Cozy Boho Vibe in Heart of Logan Square
2 bedrooms, 2 queen beds
2–7 Jan
4.96 out of 5 average rating, 85 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
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