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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in West Town
The Penthouse Gallery at OHC
3 bedrooms, 3 beds, 2 private bathrooms
5–10 Jul
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4.92 out of 5 average rating, 541 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
1–6 Jul
4.97 out of 5 average rating, 76 reviews
Top guest favourite
Room in Roscoe Village
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
3 beds, 1 bathroom
25–30 Oct
4.95 out of 5 average rating, 678 reviews
Top guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 9 reviews
Flat in West Rogers Park
Northside Chicago Apartment
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
New place to stay
Flat in Belmont Cragin
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 5 reviews
Flat in Rogers Park Township
Lake Shore Condo | Beach | North Chicago
2 bedrooms, 2 beds, 1.5 bathrooms
26–31 Jul
4.67 out of 5 average rating, 3 reviews
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 14 reviews
Home in West Town
Comfortable welcoming stay for business or leisure
3 bedrooms, 4 beds, 1 bathroom
1–6 Jul
New place to stay
Top guest favourite
Flat in North Side
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
4.93 out of 5 average rating, 336 reviews
Guest favourite
Apartment in South Side
The Langley Luxe modern style unit
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Flat in Bridgeport
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.98 out of 5 average rating, 128 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 110 reviews
Superhost
Apartment in Lincoln Park
Elegant Historic Duplex | Old Town • Lincoln Park
2 bedrooms, 3 beds, 2.5 bathrooms
23–28 Aug
New place to stay
Top guest favourite
Flat in North Side
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Ravenswood
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 54 reviews