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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Bridgeport
Prime Bridgeport – McGuane Park
2 bedrooms, 3 beds, 1 private bathroom
9–14 Aug
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4.94 out of 5 average rating, 126 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
4.97 out of 5 average rating, 76 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Jul
Home in South Side
Designer Home | Steps to the Obama Center & Beach
New place to stay, 5 bedrooms, 10 beds, 3.5 bathrooms
1–6 Jul
Guest favourite
Flat in Belmont Cragin
Modern 2 BR Retreat Steps From Family Park
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 52 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
5.0 out of 5 average rating, 15 reviews, 4 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 2 bathrooms
3–8 Jul
Top guest favourite
Room in Roscoe Village
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
4.95 out of 5 average rating, 678 reviews, 3 beds, 1 bathroom
25–30 Oct
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Guest favourite
Flat in West Side
Millennium Park 10 Min, Parking, Balcony, Sleeps 8
4.97 out of 5 average rating, 158 reviews, 2 bedrooms, 4 beds, 2 bathrooms
3–8 Jul
Flat in West Rogers Park
Northside Chicago Apartment
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
Home in West Town
Comfortable welcoming stay for business or leisure
New place to stay, 3 bedrooms, 4 beds, 1 bathroom
1–6 Jul
Guest favourite
Flat in Wicker Park
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Guest house in West Town
Upscale Wicker Park Retreat
New place to stay, 4 bedrooms, 8 beds, 3 bathrooms
12–17 Jul
Guest favourite
Apartment in South Side
The Langley Luxe modern style unit
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Top guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Flat in Bridgeport
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
4.98 out of 5 average rating, 129 reviews, 2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
Top guest favourite
Flat in North Side
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
4.93 out of 5 average rating, 336 reviews, 2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
Superhost
Flat in West Town
Modern 4BR West Town Duplex | Best for LongStays
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
1–6 Jul