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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
Apartment in Chicago
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
4.88 out of 5 average rating, 475 reviews, 2 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 64 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
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
Home in Chicago
Chicago Row House Garden Apartmt
4.95 out of 5 average rating, 55 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Oct
Guest favourite
Place to stay in Chicago
Large Brand New Room in Hyde Park Close toDowntown
4.95 out of 5 average rating, 21 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Oct
Flat in Chicago
Cozy Apartment in Pilsen | 2BR 2B | 15 Min to Town
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Room in Chicago
Lovely Front Room in a New Renovated Apartment
4.91 out of 5 average rating, 102 reviews, 2 single beds, 1 bathroom
22–27 Sept
Guest favourite
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Top guest favourite
Flat in Chicago
*Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
4.94 out of 5 average rating, 216 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
Top guest favourite
Flat in Forest Park
1 bedroom garden apartment in Forest Park
4.98 out of 5 average rating, 184 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Sept – 3 Oct
Superhost
Place to stay in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
4.89 out of 5 average rating, 45 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Oct
Top guest favourite
Room in Chicago
Spacious & serene in hip spot. Sleeps 4.
4.92 out of 5 average rating, 519 reviews, 1 queen bed, 1 bathroom
16–21 Aug
Top guest favourite
Rooms in Oak Park
Single bedroom with Asian decor in family home
4.94 out of 5 average rating, 382 reviews, 2 bedrooms, 1 double bed, 1 bathroom
17–22 Aug
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
4.94 out of 5 average rating, 140 reviews, 1 single bed, 1 bathroom
5–10 Jul
Top guest favourite
Flat in Chicago
Millennium Park 10 Min, Parking, Balcony, Sleeps 8
4.97 out of 5 average rating, 158 reviews, 2 bedrooms, 4 beds, 2 bathrooms
3–8 Jul
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 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