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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
2BR Retreat with a Fireplace in Gold Coast
2 bedrooms, 2 beds, 2.5 private bathrooms
30 Aug – 4 Sept
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4.96 out of 5 average rating, 210 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
3–8 Jul
4.97 out of 5 average rating, 77 reviews
Superhost
Home in Chicago
Cozy Luxury Escape Amazing location private home
3 bedrooms, 3 beds, 2 bathrooms
2–7 Jul
New place to stay
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
1 single bed, 1 bathroom
19–24 Sept
4.94 out of 5 average rating, 140 reviews
Place to stay in Palatine
Private King Room A | Private Bathroom
1 bedroom, 1 king bed, 1 bathroom
14–19 Jul
New place to stay
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 52 reviews
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, 11 reviews
Top guest favourite
Home in Evanston
1/2 mile to NU, 5min walk to Lake, Swim Spa Pool
5 bedrooms, 7 beds, 3.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds, 1 bathroom
14–19 Jul
5.0 out of 5 average rating, 6 reviews
Superhost
Place to stay in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bedroom, 1 bed, 1 bathroom
24–29 Oct
4.89 out of 5 average rating, 45 reviews
Room in Chicago
Comfortable bed with Smart stand
1 queen bed, 1 bathroom
18–23 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
4.93 out of 5 average rating, 337 reviews
Superhost
Flat in Chicago
Modern 4BR West Town Duplex | Best for LongStays
4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Jul
5.0 out of 5 average rating, 7 reviews
Home in Chicago
Comfortable welcoming stay for business or leisure
3 bedrooms, 4 beds, 1 bathroom
2–7 Jul
New place to stay
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Luxe
Flat in Chicago
Luxury Downtown 4BR | Exclusive Design PH
4 bedrooms, 5 beds, 3.5 bathrooms
2–7 Jul
4.97 out of 5 average rating, 39 reviews