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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in West Town
Private rooftop | Breathtaking skyline view
2 bedrooms, 3 beds, 2 private bathrooms
28 Sept – 3 Oct
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5.0 out of 5 average rating, 68 reviews
Featured hotel
Room in Downtown Chicago
Level studio suite
1 bathroom
21–26 Oct
Featured hotel
Rooms in Downtown Chicago
Junior two bedroom suite
2 bedrooms, 1 bathroom
18–23 Oct
Top guest favourite
Flat in Logan Square
Chic & Cozy Boho Vibe in Heart of Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Jan
4.96 out of 5 average rating, 85 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
11–16 Jan
4.95 out of 5 average rating, 132 reviews
Featured hotel
Hotel in West Loop
Deluxe double
1 bedroom, 2 double beds, 1 bathroom
23–28 Sept
4.92 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
16–21 Nov
5.0 out of 5 average rating, 60 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.98 out of 5 average rating, 41 reviews
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 bathroom
2–7 Nov
4.92 out of 5 average rating, 75 reviews
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 15 reviews
Guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 74 reviews
Top guest favourite
Guest house in Little Italy
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Dec
4.99 out of 5 average rating, 962 reviews
Superhost
Flat in West Side
Pilsen Stay | Primary King | Mins to downtown
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
New place to stay
Top guest favourite
Flat in Logan Square
Paradise on the Boulevard!
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 109 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Logan Square
Prime Logan Square apartment
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
28 Nov – 3 Dec
4.96 out of 5 average rating, 315 reviews
Guest favourite
Flat in West Town
Spacious & New Industrial Condo Close to Downtown
3 bedrooms, 4 queen beds, 2 bathrooms
4–9 Oct
4.9 out of 5 average rating, 302 reviews