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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago Loop
Lavish 2BR/2BA Loft I Next to Grant Park & Museums
2 bedrooms, 2 beds, 2 private bathrooms
21–26 Aug
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4.95 out of 5 average rating, 250 reviews
Top guest favourite
Flat in West Side
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 Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
1–6 Jul
4.97 out of 5 average rating, 76 reviews
Home in South Side
Designer Home | Steps to the Obama Center & Beach
5 bedrooms, 10 beds
1–6 Jul
New place to stay
Guest favourite
Flat in Belmont Cragin
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
5–10 Jul
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms, 4 beds
11–16 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Room in Roscoe Village
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
3 beds
25–30 Oct
4.95 out of 5 average rating, 678 reviews
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
3–8 Jul
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
23–28 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in West Side
Millennium Park 10 Min, Parking, Balcony, Sleeps 8
2 bedrooms, 4 beds
3–8 Jul
4.97 out of 5 average rating, 158 reviews
Flat in West Rogers Park
Northside Chicago Apartment
2 bedrooms, 2 beds
7–12 Sept
New place to stay
Home in West Town
Comfortable welcoming stay for business or leisure
3 bedrooms, 4 beds
1–6 Jul
New place to stay
Guest favourite
Flat in Wicker Park
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Guest house in West Town
Upscale Wicker Park Retreat
4 bedrooms, 8 beds
12–17 Jul
New place to stay
Top guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds
5–10 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Bridgeport
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds
21–26 Sept
4.98 out of 5 average rating, 129 reviews
Top guest favourite
Flat in North Side
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds
5–10 Jul
4.93 out of 5 average rating, 336 reviews
Superhost
Flat in West Town
Modern 4BR West Town Duplex | Best for LongStays
4 bedrooms, 6 beds
1–6 Jul
5.0 out of 5 average rating, 7 reviews