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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Modern+Spacious Inn Little Italy Near W Loop W/PKG
4 bedrooms, 4 beds, 2 private bathrooms
7–12 Nov
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4.99 out of 5 average rating, 338 reviews
Home in Chicago
House in Chicago
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
27 Dec – 1 Jan
4.95 out of 5 average rating, 126 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
7–12 Aug
New place to stay
Top guest favourite
Home in Chicago
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 Chicago
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
Home in Chicago
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
Flat in Chicago
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 Chicago
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
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.88 out of 5 average rating, 439 reviews
Top guest favourite
Flat in Chicago
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
Guest favourite
Flat in Chicago
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 Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 76 reviews
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Chicago
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
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
4–9 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 Chicago
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
Flat in Chicago
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