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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Private rooftop | Breathtaking skyline view
2 bedrooms, 3 beds, 2 private bathrooms
10–15 Aug
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5.0 out of 5 average rating, 59 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
25–30 Oct
5.0 out of 5 average rating, 48 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
Room in Chicago
Spacious garden level suite
1 queen bed
1–6 Nov
4.96 out of 5 average rating, 312 reviews
Flat in Chicago
Cozy Apartment in Pilsen | 2BR 2B | 15 Min to Town
2 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Room in Chicago
Spacious & serene in hip spot. Sleeps 4.
1 queen bed
16–21 Aug
4.92 out of 5 average rating, 520 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
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
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
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
15–20 Aug
4.95 out of 5 average rating, 64 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 52 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
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
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms
14–19 Aug
4.95 out of 5 average rating, 19 reviews
Superhost
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
15–20 Aug
4.96 out of 5 average rating, 160 reviews
Top guest favourite
Flat in Chicago
Fun & cozy getaway w/POOL/game room/FREE parking
1 bedroom, 3 queen beds
12–17 Jul
4.98 out of 5 average rating, 156 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
Guest favourite
Room in Chicago
ChicagoChinatownCenterB
1 single bed
29 Aug – 3 Sept
4.93 out of 5 average rating, 55 reviews