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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Downtown Chicago
2br/2ba, A+ location by Mag mile, views & spacious
2 bedrooms, 4 beds, 2 private bathrooms
23–28 Dec
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4.93 out of 5 average rating, 117 reviews
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
4–9 Jul
4.95 out of 5 average rating, 41 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
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 bathroom
5–10 Jul
4.98 out of 5 average rating, 81 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Apartment in South Side
The Langley Luxe modern style unit
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in West Side
Cozy Urban View Retreat Near Downtown - Sleeps 7
2 bedrooms, 4 beds, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Albany Park
NorthSide Chicago duplex 5-BD,2King size-free park
5 bedrooms, 6 beds, 2 bathrooms
8–13 Nov
4.97 out of 5 average rating, 198 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Flat in Portage Park
NW Chicago Garden Apartment
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
4.92 out of 5 average rating, 51 reviews
Flat in West Rogers Park
Northside Chicago Apartment
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
New place to stay
Guest favourite
Flat in Belmont Cragin
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds, 1 bathroom
17–22 Jul
5.0 out of 5 average rating, 6 reviews
Home in South Side
Modern 3BR Near Obama Center, UChicago & McCormick
3 bedrooms, 3 queen beds, 1 bathroom
14–19 Jul
New place to stay
Guest favourite
Home in Humboldt Park
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
New place to stay
Guest favourite
Flat in Wicker Park
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Downtown Chicago
Beautiful 2BR Apartment in Old Town
2 bedrooms, 3 beds, 1 bathroom
6–11 Jul
4.89 out of 5 average rating, 298 reviews
Superhost
Flat in West Side
10 Min to Downtown | 3BR 2BA Spacious Home
3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 3 reviews