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Vacation Rentals in Chicago

See all Vacation Rentals in Chicago
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

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 ...

Sunny Studio in Gold Coast by Sonder

Sunny Studio in Gold Coast by Sonder

East Bellevue Place and N Rush St, Chicago
3.0 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 ...

Chicago Guest House on Lakewood Avenue

Chicago Guest House on Lakewood Avenue

3715 N. Lakewood Avenue, Chicago
4.0 out of 5.0

Located in Wrigleyville, this apartment is within 1 mi (2 km) of Vic Theatre and Wrigley Field. Lincoln Park and Lincoln Park Zoo are also within 3 mi (5 ...

Spacious 3BR in Lincoln Park by Sonder

Spacious 3BR in Lincoln Park by Sonder

West Fullerton Avenue and Ashland Avenue, Chicago
4.0 out of 5.0

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 ...

Hip 3BR in Wicker Park by Sonder

Hip 3BR in Wicker Park by Sonder

West Division Street and Leavitt Street, Chicago
3.5 out of 5.0

Located in West Town, this apartment is 1.1 mi (1.8 km) from Humboldt Park and within 3 mi (5 km) of United Center and Merchandise Mart. Steppenwolf Theatre ...

Chicago Guest House on Newport Avenue

Chicago Guest House on Newport Avenue

1216 W Newport Avenue, Chicago
4.0 out of 5.0

Located in Lakeview, this apartment is within 1 mi (2 km) of Vic Theatre and Wrigley Field. Lincoln Park and Lincoln Park Zoo are also within 3 mi (5 km).

Classic 3BR in Lake View by Sonder

Classic 3BR in Lake View by Sonder

North Seminary Avenue and W School St, Chicago
3.5 out of 5.0

Located in Lakeview, this apartment is within a 15-minute walk of Vic Theatre and Wrigley Field. Lincoln Park and Lincoln Park Zoo are also within 3 mi (5 ...

Lovely 3BR in Lake View by Sonder

Lovely 3BR in Lake View by Sonder

North Seminary Avenue and W School St, Chicago
3.5 out of 5.0

Located in Lakeview, this apartment is within a 15-minute walk of Vic Theatre and Wrigley Field. Lincoln Park and Lincoln Park Zoo are also within 3 mi (5 ...

Available! 3BR Penthouse Downtown River North! Walk Everywhere Like Mag Mile!

Available! 3BR Penthouse Downtown River North! Walk Everywhere Like Mag Mile!

469 W Huron St, Chicago

Located in Near North Side, this apartment is within 1 mi (2 km) of Holy Name Cathedral, John Hancock Center, and Merchandise Mart. Chicago Water Tower and Tribune ...

Hip 2BR in Lincoln Park by Sonder

Hip 2BR in Lincoln Park by Sonder

North Halsted Street and W Schubert, Chicago
3.5 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 ...

Contemporary 2BR in Lincoln Park by Sonder

Contemporary 2BR in Lincoln Park by Sonder

West Fullerton Avenue and Greenview, Chicago
3.5 out of 5.0

Located in Lincoln Park, this apartment is 0.9 mi (1.4 km) from Lincoln Hall and within 3 mi (5 km) of Wrigley Field and Lincoln Park Zoo. Lincoln Park is 2.9 ...

Bright 2BR in Bucktown by Sonder

Bright 2BR in Bucktown by Sonder

North Damen Avenue and W Willow St, Chicago
4.0 out of 5.0

Located in West Town, this apartment is within 3 mi (5 km) of Humboldt Park, United Center, and Lincoln Park Zoo. Merchandise Mart is 3 mi (4.9 km) away.

Bright 2BR in Lincoln Park by Sonder

Bright 2BR in Lincoln Park by Sonder

West Fullerton Avenue and N Ashland Ave, Chicago
3.5 out of 5.0

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 ...

Loop Suites

Loop Suites

65 E Washington Street, Chicago
3.5 out of 5.0

Located in The Loop, this aparthotel is steps from Chicago Cultural Center and Millennium Park. Art Institute of Chicago and Chicago Theatre are also within ...

$49

$49
Pittsfield Apartments + Suites

Pittsfield Apartments + Suites

55 E Washington St., Chicago
3.0 out of 5.0
2.2 out of 5 (5 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 ...

$35

$35
Ginosi Plymouth Apartel

Ginosi Plymouth Apartel

417 South Dearborn Street, Chicago
3.5 out of 5.0

Located in The Loop, this aparthotel is within a 10-minute walk of Chicago Board of Trade Building, Willis Tower, and Skydeck Ledge. Art Institute of Chicago ...

$67

$67
Upper Wacker Drive Condo #226398 by RedAwning

Upper Wacker Drive Condo #226398 by RedAwning

71 E Upper Wacker Dr, Chicago
3.5 out of 5.0

Located in The Loop, this condo is within a 10-minute walk of Chicago Theatre, Millennium Park, and Chicago Cultural Center. Ford Center for the Performing Arts ...

Upper Wacker Drive Condo #228874 by RedAwning

Upper Wacker Drive Condo #228874 by RedAwning

71 E Upper Wacker Dr, Chicago
3.5 out of 5.0

Located in The Loop, this condo is within a 10-minute walk of Chicago Theatre, Millennium Park, and Chicago Cultural Center. Ford Center for the Performing Arts ...

Comfort Suites Michigan Avenue Loop

Comfort Suites Michigan Avenue Loop

320 N. Michigan Avenue, Chicago
3.0 out of 5.0
4.5 out of 5 (33 reviews)

Located in The Loop, this aparthotel is within a 10-minute walk of Wrigley Building, Millennium Park, and Tribune Tower. Chicago Theatre and Chicago Cultural ...

$99

$99
Luxury 3bdrm 2 Bath Condo Downtown Chicago 2000sqft

Luxury 3bdrm 2 Bath Condo Downtown Chicago 2000sqft

901 plymouth ct, Chicago

Located in the heart of Chicago, this property is within walking distance of Columbia College Chicago, Grant Park, and Buckingham Fountain. Also nearby are Art ...

$399

$399
Map

Chicago is a city with many nicknames. The Windy City’s impressive skyline glitters across Lake Michigan, inspiring Carl Sandburg to dub it the City of Big Shoulders when it became the birthplace of the skyscraper. As the home of a rich Blues music tradition, Chicago has also been called Toddlin’ Town and Sweet Home Chicago by voices such as Frank Sinatra and Robert Johnson. Get to know the many names of faces of this great city like a local from our Chicago vacation rentals.

The Local Life

Locals know that exploring Chicago’s best kept secrets is about digging deeper. Sure, try the obligatory Chicago dog, but then head to that corner gourmet dog store for something completely unique, like a chicken, apple, and cranberry dog. Go ahead, wolf it down. We won’t judge.

Enjoy views of famous buildings such as the John Hancock Center, Tribune Tower, and Chicago Water Tower, or be part of the skyline at Embassy Suites Chicago Downtown Magnificent Mile. Locals love the area because it’s so close to the Chicago Riverwalk and the famous Millennium Park.

The Chicago Institute of Art draws admirers from around the world, but the Museum of Contemporary Photography and the Chicago Cultural Center provide inspiration for those who are willing to venture off the beaten path. Luckily, the Ginosi Basics Loop Apartel is close by and features a classy lobby that’s photogenic enough for your own photography exhibit on social media. You can call that shot Untitled #4, or simply #Chicagovacation.

See a side of Chicago most visitors miss, then relax in one of Travelocity’s vacation rentals, where it feels like Sweet Home Chicago.

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