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Vacation Rentals in Chicago

See all Vacation Rentals in Chicago
Pittsfield Apartments + Suites

Pittsfield Apartments + Suites

55 E Washington St., Chicago
3.0 out of 5.0
2.3 out of 5 (6 reviews)

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

$54

$54
Comfort Suites Michigan Avenue Loop

Comfort Suites Michigan Avenue Loop

320 N. Michigan Avenue, Chicago
3.5 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
Loop Suites

Loop Suites

55 E Washington Street, Chicago
4.0 out of 5.0

Located in The Loop, this aparthotel is steps from Chicago Cultural Center and Millennium Park.

$29

$29
Celeste Celebrity Suites

Celeste Celebrity Suites

68 E Cedar St, Chicago
4.0 out of 5.0
5.0 out of 5 (1 reviews)

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

$192

$192
Ginosi Plymouth Apartel

Ginosi Plymouth Apartel

417 South Dearborn Street, Chicago
4.0 out of 5.0

This aparthotel is located in Chicago (The Loop), close to Chicago Board of Trade Building, Art Institute of Chicago, and Willis Tower. Also nearby are Skydeck ...

$55

$55
Magnolia Coach House

Magnolia Coach House

5705 N Magnolia Ave, Chicago
4.0 out of 5.0
5.0 out of 5 (1 reviews)

Located in Edgewater, this apartment building is 1.1 mi (1.7 km) from Loyola University Chicago and within 3 mi (5 km) of Wrigley Field and Lincoln Park. Montrose ...

Furnished Suites Near Navy Pier

Furnished Suites Near Navy Pier

420 East Ohio Chicago, IL 60611, Chicago
4.0 out of 5.0
5.0 out of 5 (1 reviews)

Located in Near North Side, this apartment building is within a 10-minute walk of Navy Pier and Chicago Children's Museum. Tribune Tower and Wrigley Building ...

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
4.0 out of 5 (4 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 ...

$72

$72
Chicago Downtown Condo - Michigan Ave Suite ID #14-15

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

1255 S. Michigan Avenue, Chicago
3.0 out of 5.0

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

Spacious 3bdrm 2 Bath Condo Downtown Chicago 2000sqft

Spacious 3bdrm 2 Bath Condo Downtown Chicago 2000sqft

901 plymouth ct, Chicago

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

$199

$199
Extended Stay America Chicago - Romeoville

Extended Stay America Chicago - Romeoville

1225 Lakeview Dr, Romeoville
3.0 out of 5.0
4.0 out of 5 (2 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 Private Room in Condo off of Lake Michigan

Beautiful Private Room in Condo off of Lake Michigan

6166 N Sheridan Rd, Chicago

Situated in Chicago, this property is close to Loyola University Chicago, Aragon Ballroom, and Montrose Beach. Local attractions also include Swedish Covenant ...

$45

$45
The Downtown Chicago Loft With City View Roof Deck - Perfect for Large Groups!

The Downtown Chicago Loft With City View Roof Deck - Perfect for Large Groups!

1440 N Cleveland Ave, Chicago

This property is located in Chicago (Near North Side), close to Steppenwolf Theatre, John Hancock Center, and Lincoln Park Zoo. Also nearby are Chicago Water ...

$299

$299
South Loop Luxury Lofts

South Loop Luxury Lofts

2973 S Archer Ave, Chicago

This property is located in Chicago (Canalport), close to Guaranteed Rate Field, University of Illinois Chicago, and McCormick Place. Local attractions also ...

$150

$150
Stay Alfred Apartments on Wabash

Stay Alfred Apartments on Wabash

1333 S. Wabash Avenue, Chicago
4.5 out of 5.0

This apartment building is located in Chicago (Near South Side), close to Field Museum of Natural History, Soldier Field, and John G. Shedd Aquarium. Also nearby ...

$104

$104
Extended Stay America Chicago - Vernon Hills - Lake Forest

Extended Stay America Chicago - Vernon Hills - Lake Forest

215 N Milwaukee Ave, Vernon Hills
3.0 out of 5.0
3.2 out of 5 (5 reviews)

Situated in Vernon Hills, this aparthotel is 1.6 mi (2.6 km) from Cuneo Mansion and Gardens and within 6 mi (10 km) of Trinity International University and Lambs ...

$67

$67
Furnished Suites in South Loop Chicago

Furnished Suites in South Loop Chicago

1333 S Wabash Ave, Chicago
4.0 out of 5.0
3.0 out of 5 (1 reviews)

Located in Near South Side, this apartment building is within 1 mi (2 km) of Columbia College Chicago, Art Institute of Chicago, and McCormick Place. Grant Park ...

Stunning 3BR in Lake View by Sonder

Stunning 3BR in Lake View by Sonder

West Barry Avenue and N Lakewood Ave, Chicago
4.5 out of 5.0

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

The Four Story Wicker Park Dream Home With 9 King Beds and Panoramic City Views

The Four Story Wicker Park Dream Home With 9 King Beds and Panoramic City Views

1342 Greenview Ave, Chicago

This property is located in Chicago (West Town), close to Steppenwolf Theatre, Lincoln Hall, and Apollo Theater Chicago. Also nearby are Second City and Park ...

$199

$199
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 building is within a 10-minute walk of John Hancock Center and Chicago Water Tower. Tribune Tower and Wrigley Building ...

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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