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Search results; Over 1,000 homes in Chicago

Superhost
Flat in Chicago
Spectacular 2BR Penthouse in the Loop | Roof Deck
2 bedrooms, 3 beds, 2 private bathrooms
30 Aug – 4 Sept
,
4.82 out of 5 average rating, 348 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
4–9 Oct
4.93 out of 5 average rating, 27 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
2–7 Aug
4.93 out of 5 average rating, 107 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
19–24 Dec
4.95 out of 5 average rating, 126 reviews
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
21–26 Aug
New place to stay
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds
8–13 Aug
New place to stay
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
15–20 Nov
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Flat in Chicago
Best City Views • Rooftop Nights • EV Garage Free
2 bedrooms, 6 beds
2–7 Aug
4.98 out of 5 average rating, 88 reviews
Top guest favourite
Room in Chicago
Spacious & serene in hip spot. Sleeps 4.
1 queen bed
16–21 Aug
4.92 out of 5 average rating, 525 reviews
Top guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds
25–30 Oct
4.94 out of 5 average rating, 252 reviews
Guest favourite
Room in Bridgeview
Comfortable Private Room with Easy Chicago Access
1 queen bed
16–21 Aug
5.0 out of 5 average rating, 18 reviews
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds
16–21 Aug
New place to stay
Top guest favourite
Flat in Chicago
Cozy & Spacious Sunny 2 bedroom apartment.
2 bedrooms, 2 beds
19–24 Oct
4.98 out of 5 average rating, 108 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed
10–15 Nov
4.96 out of 5 average rating, 319 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 305 reviews
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms, 4 beds
11–16 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Chicago
An elegant Chicago Northside Getaway
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 374 reviews
Flat in Chicago
The Clubhouse at Wrigley | Sleeps 10
4 bedrooms, 6 beds
24–29 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
3–8 Dec
4.99 out of 5 average rating, 108 reviews