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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Chicago
River North | Private Deck With In&Out Parking
3 bedrooms, 4 beds, 2 private bathrooms
2–7 Oct
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4.9 out of 5 average rating, 82 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
Guest favourite
Flat in Chicago
Modern 6BR Suite with Pool-table near McCormick
6 bedrooms, 6 king beds
20–25 Sept
4.92 out of 5 average rating, 38 reviews
Guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 21 reviews
Guest favourite
Flat in Chicago
Spacious 3bd/3ba Apt in West Town - Next to Kasama
3 bedrooms, 3 beds
21–26 Sept
4.9 out of 5 average rating, 30 reviews
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 166 reviews
Guest favourite
Home in Chicago
Home in Bucktown | Park for Free | Walk to Train
5 bedrooms, 5 king beds
24–29 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
6–11 Sept
5.0 out of 5 average rating, 57 reviews
Guest favourite
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
20–25 Sept
4.91 out of 5 average rating, 11 reviews
Guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
7–12 Sept
4.95 out of 5 average rating, 44 reviews
Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
9 bedrooms, 15 beds
20–25 Sept
4.8 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Chicago
Stylish & Spacious Multi-Level Apt in Wicker Park
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 35 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 130 reviews
Flat in Chicago
Rooftop, West Loop Chicago
3 bedrooms, 3 beds
14–19 Oct
New place to stay
Guest favourite
Townhouse in Chicago
Walk to United Center 9 mins-Downtown Free Parking
3 bedrooms, 3 beds
26 Sept – 1 Oct
4.89 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds
7–12 Sept
4.91 out of 5 average rating, 79 reviews
Guest favourite
Home in Chicago
Maison Blanc Noir ~ Chicago Mansion w/ King Beds
5 bedrooms, 8 beds
7–12 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Chicago
Explore Chicago • Private Parking • Museum Access
2 bedrooms, 4 beds
28 Sept – 3 Oct
4.96 out of 5 average rating, 25 reviews