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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Large Remodeled Home in Lincoln Park, Sleeps 12!
4 bedrooms, 5 beds, 3 private bathrooms
9–14 Aug
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4.97 out of 5 average rating, 139 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.97 out of 5 average rating, 76 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Jul
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Superhost
Apartment in Chicago
Elegant Historic Duplex | Old Town • Lincoln Park
New place to stay, 2 bedrooms, 3 beds, 2.5 bathrooms
23–28 Aug
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Flat in Chicago
Northside Chicago Apartment
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
Home in Chicago
Comfortable welcoming stay for business or leisure
New place to stay, 3 bedrooms, 4 beds, 1 bathroom
1–6 Jul
Top guest favourite
Guest house in Evanston
Welcome to Serenity.
5.0 out of 5 average rating, 21 reviews, 1 bedroom, 1 bed, 1 bathroom
29 Aug – 3 Sept
Guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
4.91 out of 5 average rating, 188 reviews, 3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Room in Chicago
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
4.95 out of 5 average rating, 678 reviews, 3 beds, 1 bathroom
25–30 Oct
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Top guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Top guest favourite
Flat in Chicago
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
4.98 out of 5 average rating, 129 reviews, 2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
Home in Chicago
Designer Home | Steps to the Obama Center & Beach
New place to stay, 5 bedrooms, 10 beds, 3.5 bathrooms
1–6 Jul
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
4.93 out of 5 average rating, 337 reviews, 2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
Place to stay in Chicago
Happy Homes U&I – Quiet Basement Retreat
New place to stay, 1 bedroom, 1 bed, 2 bathrooms
1–6 Jul
Top guest favourite
Apartment in Chicago
CHIC DOWNTOWN PENTHOUSE w/ private roof +parking
4.93 out of 5 average rating, 214 reviews, 2 bedrooms, 3 beds, 2 bathrooms
4–9 Jul