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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Edgewater
Andersonville Living
3 bedrooms, 5 beds, 1 private bathroom
30 Oct – 4 Nov
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4.94 out of 5 average rating, 491 reviews
Home in Edgewater
House in Chicago
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
New place to stay
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
27 Dec – 1 Jan
4.95 out of 5 average rating, 126 reviews
Home in Belmont Cragin
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 24 reviews
Apartment in Wicker Park
Ukrainian Village 2 Bd/2ba - Steps from Division!
2 bedrooms, 2 queen beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Room in Bridgeport
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
16–21 Aug
New place to stay
Guest favourite
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Bridgeport
Post-Punk & Industrial Museum Apt - 4BR Bridgeport
4 bedrooms, 5 beds, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 29 reviews
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 68 reviews
Top guest favourite
Flat in Irving Park
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds, 1 bathroom
27 Jan – 1 Feb
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
5–10 Aug
4.91 out of 5 average rating, 111 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 118 reviews
Top guest favourite
Flat in Hyde Park
Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!
5 bedrooms, 6 beds, 3 bathrooms
30 Aug – 4 Sept
4.94 out of 5 average rating, 577 reviews
Top guest favourite
Home in Chicago
Big house in the BEST Location!
3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Bridgeport
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.99 out of 5 average rating, 135 reviews
Top guest favourite
Flat in Downtown Chicago
Luxury Loft Collection COMBO 01/03 | Terrace
6 bedrooms, 15 beds, 6 bathrooms
1–6 Nov
5.0 out of 5 average rating, 17 reviews