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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
The Woodsman's Gallery at OHC
3 bedrooms, 4 beds, 2 private bathrooms
26–31 Jul
,
4.9 out of 5 average rating, 621 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
16–21 Aug
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
12–17 Oct
4.96 out of 5 average rating, 54 reviews
Guest favourite
Apartment in Chicago
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds
5–10 Jul
4.88 out of 5 average rating, 473 reviews
Flat in Chicago
Cozy Apartment in Pilsen | 2BR 2B | 15 Min to Town
2 bedrooms, 3 beds
27 Sept – 2 Oct
New place to stay
Top guest favourite
Guest suite in Chicago
2BR/1.5 Bath in Logan Square
2 bedrooms, 2 queen beds
28 Nov – 3 Dec
4.95 out of 5 average rating, 59 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed
14–19 Mar
4.96 out of 5 average rating, 309 reviews
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds
16–21 Aug
4.88 out of 5 average rating, 433 reviews
Guest favourite
Rooms in Chicago
Spacious Haven in North Park
3 bedrooms, 4 beds
4–9 Oct
4.89 out of 5 average rating, 64 reviews
Top guest favourite
Flat in Forest Park
1 bedroom garden apartment in Forest Park
1 bedroom, 2 beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 184 reviews
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds
5–10 Jul
4.93 out of 5 average rating, 336 reviews
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Rooms in Oak Park
Single bedroom with Asian decor in family home
2 bedrooms, 1 double bed
17–22 Aug
4.94 out of 5 average rating, 381 reviews
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
1 single bed
19–24 Sept
4.94 out of 5 average rating, 140 reviews
Top guest favourite
Room in Chicago
Al's Oasis Chicago
1 queen bed
5–10 Jul
4.96 out of 5 average rating, 228 reviews
Top guest favourite
Flat in Forest Park
Like a Treehouse!
1 bedroom, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 371 reviews
Guest favourite
Flat in Chicago
iKlektik House Chicago/Cardinal
1 bedroom, 1 king bed
5–10 Jul
4.91 out of 5 average rating, 487 reviews
Top guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds
29 Aug – 3 Sept
4.9 out of 5 average rating, 500 reviews