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Vacation Rentals in Chicago

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Pittsfield Apartments + Suites

Pittsfield Apartments + Suites

55 E Washington St., Chicago
3.5 out of 5.0
Last booking: 21 hours ago
28 others viewing this property now
3.0 out of 5 (565 reviews)

Located in The Loop, this apartment is steps from Chicago Cultural Center and Millennium Park. Art Institute of Chicago and Ford Center for the Performing Arts ...

$45

$45
Stay Alfred Apartments on Illinois St.

Stay Alfred Apartments on Illinois St.

220 W Illinois St, Chicago
5.0 out of 5.0
Last booking: 5 days ago
4.3 out of 5 (3 reviews)

Located in Near North Side, this apartment is within a 15-minute walk of Merchandise Mart, Wrigley Building, and Tribune Tower. Willis Tower and Skydeck Ledge ...

$166

$166
Extended Stay America Chicago - Hillside

Extended Stay America Chicago - Hillside

4575 Frontage Rd, Hillside
3.0 out of 5.0
Last booking: 12 hours ago
2 others viewing this property now
3.3 out of 5 (415 reviews)

Situated in Hillside, this aparthotel is 2.1 mi (3.5 km) from Stevenson Park and within 6 mi (10 km) of Brookfield Zoo and Oak Brook Golf Course. Oakbrook Center ...

$67

$67
Extended Stay America Chicago - Skokie

Extended Stay America Chicago - Skokie

5211 Old Orchard Rd, Skokie
3.0 out of 5.0
Last booking: 17 hours ago
20 others viewing this property now
3.4 out of 5 (443 reviews)

Situated in Skokie, this aparthotel is 1.2 mi (2 km) from North Shore Center for the Performing Arts and within 3 mi (5 km) of Wagner Farm and Skokie Theatre. ...

$81

$81
Extended Stay America - Chicago- O'Hare - Allstate Arena

Extended Stay America - Chicago- O'Hare - Allstate Arena

1207 E Touhy Ave, Des Plaines
3.0 out of 5.0
Last booking: 16 hours ago
15 others viewing this property now
3.3 out of 5 (311 reviews)

Situated in Des Plaines, this aparthotel is 0.7 mi (1.1 km) from Allstate Arena and within 3 mi (5 km) of Rivers Casino and McDonald's Museum. Donald E. Stephens ...

$76

$76
Extended Stay America Chicago - Romeoville

Extended Stay America Chicago - Romeoville

1225 Lakeview Dr, Romeoville
2.5 out of 5.0
Last booking: 2 days ago
2 others viewing this property now
3.3 out of 5 (197 reviews)

Situated in Romeoville, this aparthotel is 2 mi (3.2 km) from Bolingbrook Golf Club and within 6 mi (10 km) of Naperbrook Golf Course and Mistwood Golf Club. ...

$63

$63
Beautiful Spa Like Suite on the North Side!

Beautiful Spa Like Suite on the North Side!

2415 West Belle Plaine Avenue, Chicago
1 others viewing this property now
4.8 out of 5 (35 reviews)

Located in North Center, this apartment is within 3 mi (5 km) of Swedish Covenant Hospital, Wrigley Field, and Lincoln Park. Vic Theatre and Apollo Theater Chicago ...

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Spacious Bronzeville Brownstone Gdn Level Near Downtown & University of Chicago

Spacious Bronzeville Brownstone Gdn Level Near Downtown & University of Chicago

4510 S Forrestville Ave, Chicago
Last booking: 2 days ago
5.0 out of 5 (2 reviews)

Located in Bronzeville, this bed & breakfast is within 3 mi (5 km) of Washington Park, University of Chicago, and McCormick Place. Guaranteed Rate Field and ...

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Vibrant Studio in Gold Coast by Sonder

Vibrant Studio in Gold Coast by Sonder

East Bellevue Place and N Rush St, Chicago
3.5 out of 5.0

Located in Gold Coast, this apartment is within a 10-minute walk of Newberry Library, John Hancock Center, and Chicago Water Tower. Tribune Tower and Wrigley ...

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Chicago Premier Suites

Chicago Premier Suites

540 N State Street, Chicago
4.5 out of 5.0
5.0 out of 5 (21 reviews)

Located in Near North Side, this apartment is within a 10-minute walk of Driehaus Museum, Tribune Tower, and Wrigley Building. John Hancock Center and Chicago ...

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Al Capone Unit In Beautiful Vintage Building In The Gold Coast!

Al Capone Unit In Beautiful Vintage Building In The Gold Coast!

67 East Cedar Street, Chicago
Last booking: 1 day ago
5.0 out of 5 (31 reviews)

Located in Gold Coast, this apartment is within a 10-minute walk of John Hancock Center and Chicago Water Tower. Tribune Tower and Wrigley Building are also ...

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Perfect Location! Perfect Price! Includes Breakfast and Parking, Perfect for all

Perfect Location! Perfect Price! Includes Breakfast and Parking, Perfect for all

2831 North 74th Avenue, Elmwood Park
4.8 out of 5 (31 reviews)

Located in Ellsworth, this apartment is within 6 mi (10 km) of Portage Park, Rosemont Theatre, and MB Financial Park at Rosemont. Brookfield Zoo and Humboldt ...

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Vibrant 2BR in Lincoln Park by Sonder

Vibrant 2BR in Lincoln Park by Sonder

North Halsted Street and W Schubert, Chicago
4.0 out of 5.0
4.7 out of 5 (6 reviews)

Located in Lincoln Park, this apartment is within 2 mi (3 km) of Kingston Mines, Wrigley Field, and Lincoln Park Zoo. John Hancock Center and Lincoln Park are ...

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Chicago Downtown Condo - Michigan Ave Suite ID #14-15

Chicago Downtown Condo - Michigan Ave Suite ID #14-15

1255 S. Michigan Avenue, Chicago
2.5 out of 5.0
Last booking: 5 days ago
1 others viewing this property now
3.0 out of 5 (4 reviews)

Located in Near South Side, this condo is within a 15-minute walk of Columbia College Chicago and Grant Park. Art Institute of Chicago and Millennium Park are ...

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Celeste Celebrity Suites Gold Coast!

Celeste Celebrity Suites Gold Coast!

68 East Cedar Street, Chicago
5.0 out of 5 (23 reviews)

Located in Gold Coast, this apartment is within a 10-minute walk of John Hancock Center and Chicago Water Tower. Tribune Tower and Wrigley Building are also ...

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Serene 4 Bedroom House In Lombard

Serene 4 Bedroom House In Lombard

1S060 Church Street, Lombard
5.0 out of 5 (1 reviews)

Situated in Lombard, this vacation home is within 3 mi (5 km) of Yorktown Shopping Center, Oakbrook Center Mall, and Drury Lane Theater. Lilacia Park and York ...

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Entire Trendy Unit- 15 min to Downtown Chicago! One Bedroom/ One Bathroom

Entire Trendy Unit- 15 min to Downtown Chicago! One Bedroom/ One Bathroom

4720 N Central Ave, Chicago

Located in Jefferson Park, this apartment is 1.2 mi (1.9 km) from Portage Park and within 6 mi (10 km) of Swedish Covenant Hospital and Skokie Theatre. Wrigley ...

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Mid-Century 2BR in Lincoln Park by Sonder

Mid-Century 2BR in Lincoln Park by Sonder

N Halsted St., Chicago
4.5 out of 5.0

Located in Lincoln Park, this apartment is within 2 mi (3 km) of Kingston Mines, Wrigley Field, and Lincoln Park Zoo. John Hancock Center and Lincoln Park are ...

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Posh 2BR in River West by Sonder

Posh 2BR in River West by Sonder

North Milwaukee Avenue and N Morgan St, Chicago
4.0 out of 5.0

Located in West Town, this apartment is within 2 mi (3 km) of Merchandise Mart, Willis Tower, and Skydeck Ledge. John Hancock Center and University of Illinois ...

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Sleek 3BR in Lincoln Park by Sonder

Sleek 3BR in Lincoln Park by Sonder

West Fullerton Avenue and N Ashland Ave, Chicago
4.0 out of 5.0
Last booking: 21 hours ago
5.0 out of 5 (2 reviews)

Located in Lincoln Park, this apartment is 1 mi (1.6 km) from Lincoln Hall and within 3 mi (5 km) of Wrigley Field and Lincoln Park Zoo. Lincoln Park is 3.1 ...

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Map

Choosing the perfect Chicago (and vicinity) rental

You've likely stayed at countless hotels. Maybe it's time to try a vacation rental to experience the area like a local. Stay in Chicago (and vicinity) at one of 26 vacation rentals now bookable on Expedia.com.

  • 22 apartments
  • 4 condos

Shoppers, art connoisseurs, and foodies are in for a treat, while all visitors will find something at this urban lakeside destination to delight in. Families won't want to miss the nearby concerts and theaters.

Dining in Chicago (and vicinity)

Ada Street, University Club of Chicago, and Maria's Packaged Goods and Community Bar are a few favorite spots to grab some food. Most vacation rentals come with full-size kitchens, so eating in is always an option, too.

Sightseeing around Chicago (and vicinity)

Some of the top sights in Chicago (and vicinity) include Millennium Park, Willis Tower, and Skydeck Ledge. If you're bringing the kiddos along, save a few hours for Six Flags Great America, Navy Pier, and John G. Shedd Aquarium. Culture aficionados will have plenty to take in at Chicago Cultural Center, Ford Center for the Performing Arts Oriental Theatre, and Chicago Theater. If your vacation agenda includes shopping, consider a trip to Chicago Premium Outlets and Shops at Northbridge. Outdoor enthusiasts will appreciate a jaunt through Grant Park and Lincoln Park.

Exploring the Chicago (and vicinity) area

For those arriving without a car, nearby metro stations like Monroe Station, Monroe Station, or Adams-Wabash Station provide a convenient transportation option. To travel outside the immediate area, consider taking a train from Millennium Station, Chicago Van Buren Street Station, or Chicago Union Station.

Packing for your Chicago (and vicinity) trip

Wondering what the weather will be like on your trip? Here are the seasonal average temperatures.

  • January–March: 31°F
  • April–June: 61°F
  • July–September: 72°F
  • October–December: 42°F

Booking your rental on Expedia

Expedia makes it easy and safe to book vacation rentals in Chicago (and vicinity). We can even help you contact the property owner to make special arrangements. You're sure to have a memorable trip with the convenience of a short-term rental.