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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Chicago
Can't Beat This 2min Walk to Wrigley!
2 bedrooms, 5 beds, 2 private bathrooms
29 Sept – 4 Oct
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4.81 out of 5 average rating, 278 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 12 beds
1–6 Jul
4.95 out of 5 average rating, 41 reviews
Superhost
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds
12–17 Jul
4.93 out of 5 average rating, 137 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
5–10 Jul
5.0 out of 5 average rating, 52 reviews
Home in Chicago
Designer Home | Steps to the Obama Center & Beach
5 bedrooms, 10 beds
1–6 Jul
New place to stay
Flat in Chicago
Northside Chicago Apartment
2 bedrooms, 2 beds
7–12 Sept
New place to stay
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Chicago
Best City Views • Rooftop Nights • EV Garage Free
2 bedrooms, 6 beds
1–6 Jul
4.98 out of 5 average rating, 84 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
9–14 Aug
New place to stay
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
Flat in Chicago
Easy Downtown Access from The Pilsen Haven
3 bedrooms, 3 beds
4–9 Jul
5.0 out of 5 average rating, 26 reviews
Guest favourite
Apartment in Chicago
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds
5–10 Jul
4.88 out of 5 average rating, 475 reviews
Top guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Chicago
Millennium Park 10 Min, Parking, Balcony, Sleeps 8
2 bedrooms, 4 beds
3–8 Jul
4.97 out of 5 average rating, 158 reviews
Guest favourite
Home in Norridge
Modern Ranch | 5 Min to O'Hare, 25 to Chicago
3 bedrooms, 3 beds
18–23 Jul
4.92 out of 5 average rating, 13 reviews
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds
2–7 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
1–6 Jul
4.97 out of 5 average rating, 76 reviews
Guest favourite
Flat in Chicago
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 favourite
Flat in Chicago
Bright Wrigleyville Stay | Near Transit & Parks
3 bedrooms, 4 beds
5–10 Jul
4.94 out of 5 average rating, 16 reviews