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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Chicago
Can't Beat This 2min Walk to Wrigley!
2 bedrooms, 5 beds, 2 private bathrooms
29 Sept – 4 Oct
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4.81 out of 5 average rating, 279 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
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
5–10 Jul
4.98 out of 5 average rating, 81 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
Flat in Chicago
Boho City Escape | Parking + Balcony
2 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
12–17 Oct
4.91 out of 5 average rating, 56 reviews
Top 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, 383 reviews
Guest favourite
Room in Chicago
Lovely Front Room in a New Renovated Apartment
2 single beds
22–27 Sept
4.91 out of 5 average rating, 103 reviews
Guest favourite
Place to stay in Chicago
Large Brand New Room in Hyde Park Close toDowntown
1 bedroom, 1 queen bed
23–28 Oct
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed
1–6 Nov
4.96 out of 5 average rating, 312 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Apartment in Chicago
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds
16–21 Aug
4.88 out of 5 average rating, 476 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
Sun filled tranquil 2 br great part of Logan Sq.
2 bedrooms, 2 queen beds
9–14 Aug
4.77 out of 5 average rating, 567 reviews
Top guest favourite
Flat in Chicago
NorthSide Chicago duplex 5-BD,2King size-free park
5 bedrooms, 6 beds
8–13 Nov
4.97 out of 5 average rating, 198 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Guest favourite
Flat in Chicago
Beautiful 2BR Apartment in Old Town
2 bedrooms, 3 beds
6–11 Jul
4.89 out of 5 average rating, 298 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
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
5.0 out of 5 average rating, 7 reviews