Chicago, IL Vacation Packages

Name: Chicago, IL Vacation
Brand: Tripmasters Latin America
SKU: Chicago, IL
Rating: 4.7 (1 reviews)

Chicago, on Lake Michigan in Illinois, is the third-largest city in the United States and the largest city in the Midwest region. Famed for its bold architecture, it has a skyline punctuated by skyscrapers such as the iconic John Hancock Center, 1,451-ft. Willis Tower (formerly the Sears Tower) and the neo-Gothic Tribune Tower. A must-visit place for tourists is ritzy Michigan Avenue, part of which is the famed `Magnificent Mile`. Chicago is renowned for its museums, including the Art Institute of Chicago, which sits between Grant Park and the beginning of historic Route 66.

Best Chicago, IL Vacation Packages:

Chicago and the Lake Michigan Shore (Self Drive)

7 nights from $1,351*

This self-drive, independent vacation package will introduce you to Illinois and Wisconsin. Visit Chicago, on Lake Michigan in also called `The wind city ‘and it will blow you away with its steely skyscrapers, museums and rocking festivals, then, drive to Illinois State Beach and Lake Michigan Shore South (sprawling waterfront of activity and beauty, Traveling the towns throughout the Shore you will find shopping destinations, to world-class golf courses, to family-friendly attractions and casinos). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

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Other Chicago, IL Vacation Packages:

Chicago and Illinois State Beach (Self Drive)

6 nights from $1,278*

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From Lake Erie to Lake Michigan (Cleveland - Toledo - Indiana Dunes - Chicago - Self Drive)

8 nights from $654*

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Chicago Getaway

4 nights from $176*

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Chicago and Indianapolis (Self Drive)

6 nights from $481*

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This self-drive, independent vacation package will introduce you to these beautiful cities through Illinois. Combine Chicago (The wind city will blow you away with its steely skyscrapers, museums and rocking festivals) and Illinois Beach State Park (part of the Illinois state park system and is located along Lake Michigan in Winthrop Harbor, Zion, Beach Park and unincorporated Benton Township in northeast Illinois); with a Rental Car. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Included:

Rental Car for 7 days

Hotel for 3 nights in Chicago, IL

Hotel for 3 nights in Illinois Beach State Park, IL

Driving Time
Chicago, IL- Illinois Beach State Park, IL: 1 hr 12 mins. approx.

6 nights from $1,278*

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Discover Ohio, Indiana and Illinois with this unique Self-Drive Package. Start in Cleveland (Known as "The Forest City", is the largest city on the shores of Lake Erie and the largest metropolitan economy and population in Ohio). After that, drive to Toledo and Indiana Dunes. Then Chicago (On Lake Michigan in Illinois, known for interesting architecture like the Sears Tower). This is a flexible vacation package. Select your number of nights in each city, desired hotel, and activities.

Included:

Rental Car for 9 days

Hotel for 2 nights in Cleveland, OH

Hotel for 2 nights in Toledo, OH

Hotel for 2 nights in Indiana Dunes, IN

Hotel for 2 nights in Chicago, IL

Driving Time
Cleveland - Toledo: 1 hr 48 mins. approx.
Toledo – Indiana Dunes: 3 hr. 6 mins. approx.
Indiana Dunes - Chicago: 54 mins. approx.

8 nights from $654*

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This self-drive, independent vacation package will introduce you Illinois. Visit Chicago, on Lake Michigan in also called `The wind city ‘and it will blow you away with its steely skyscrapers, museums and rocking festivals. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Included:

Rental Car for 5 days

Hotel for 4 nights in Aspen

4 nights from $176*

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Take the Midwest States of Illinois and Indiana into your own hands, travelling between these charming cities with a Rental Car. Start this trip in the sophisticated "Wind City"; Chicago (with its steely skyscrapers, museums and rocking festivals). Then, drive to Indiana and ends this trip, with a pleasant stay in "Indy" Indianapolis (the state capital, with its speeding race cars, plenty of green space, glistening waterways and remarkable memorials). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Included:

Rental Car for 4 days

Hotel for 3 nights in Chicago

Hotel for 3 nights in Indianapolis

Driving Time
Chicago - Indianapolis: 3 hrs. approx.

6 nights from $481*

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Chicago, IL

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Hotels and Activities

SUGGESTED Chicago, IL VACATION PACKAGES:

Chicago and St. Louis (Self Drive)

6 nights from $594*

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Take Illinois and Missouri into your own hands, travelling between this popular cities with a rental car. Visit Chicago (Famed for its bold architecture and renowned for its museums and many loyal sports fans) and St Louis (a major city in Missouri along the Mississippi River, known for the Gateway Arch, the tallest monument constructed in the United States). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Included:

Rental Car for 7 days
Hotel for 3 nights in Chicago
Hotel for 3 nights in St Louis
Driving Time
Chicago - St Louis: 4hr 35mn approx.

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Chicago and Indiana Dunes State Park (Self Drive)

6 nights from $1,319*

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Cosmopolitan city, open green spaces and music await you with this Self-Drive Package in these two cities in Illinois State. Start this trip with a visit to "The Windy City"; Chicago (famed for its bold architecture, with the Sears Tower; with its museums and many loyal sports fans). After that, drive to Indiana Dunes State Park (natural sand dunes occurring at the southern end of Lake Michigan in the American State of Indiana. They are known for their ecological significance). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Included:

Rental Car for 7 days
Hotel for 3 nights in Chicago, IL
Hotel for 3 nights in Indiana Dunes State Park, IN
Driving Time
Chicago, IL - Indiana Dunes State Park, IN: 53 mins. approx.
Indiana Dunes State Park, IN- South Bend: 54 mins. approx.

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Route 66 - Illinois to Oklahoma the Highlights (Self Drive)

7 nights from $569*

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Venture from east to west along the iconic Route 66, the most famous U.S. Highway System. Popular sights for families, adventurers, and lovers of small town Americana, beckon visitors to explore the heart of the country. Start in Illinois, with a stay in -The Windy City- Chicago (famed for its bold architecture and renowned for its museums and many loyal sports fans), then journey to Missouri (known as the -Show Me State- while exploring St. Louis (the Gateway Arch, the tallest monument constructed in the U.S.) and Springfield (the -Queen City of the Ozarks- which offers beautiful and scenic outdoor recreational activities). Before ending this whirlwind trip, your next stop is in Oklahoma, with a pleasant stay in its capital city; Oklahoma City (known for its cowboy culture and capital complex, surrounded by working oil wells). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Included:

Rental Car for 8 days
Hotel for 3 nights in Chicago
Hotel for 1 night in St. Louis
Hotel for 1 night in Springfield
Hotel for 2 nights in Oklahoma City
Driving Time
Chicago - St. Louis: 5 hrs 25 mins approx.
St. Louis - Springfield: 3 hrs 20 mins approx.
Springfield - Oklahoma City: 4 hrs 15 mins approx.

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Route 66 - Illinois to Texas the Long Ride (Self Drive)

15 nights from $2,593*

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Explore iconic Route 66 on a long ride from east to west, venturing through Illinois, Missouri, Oklahoma, and Texas - with nearly endless opportunities to experience culture, excitement, and beauty. Combine Chicago (set on beautiful Lake Michigan the city is well regarded for interesting architecture - like the Sears Tower - and its cultural highlights from museums to theaters and more), Springfield, Illinois (home of President Abraham Lincoln as well as his Presidential Library), St. Louis (whose beautiful and famous Gateway Arch welcomes visitors to this city on the Mississippi River), Springfield, Missouri (an Ozark city with lots of Route 66 history), Tulsa (Oklahoma`s vibrant second-largest city, with a sizable arts scene), Oklahoma City (the capital of Oklahoma and home to the National Cowboy and Western Heritage Museum and the Oklahoma City Memorial) and finally Amarillo (nicknamed -The Yellow Rose of Texas-, boasts a great food scene, historic districts, and easy access to Palo Duro Canyon). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Included:

Rental Car for 13 days
Hotel for 3 nights in Chicago
Hotel for 2 nights in Springfield, IL
Hotel for 2 nights in St. Louis
Hotel for 2 nights in Springfield, MO
Hotel for 2 nights in Tulsa
Hotel for 2 nights in Oklahoma City
Hotel for 2 nights in Amarillo
Driving Time
Chicago– Springfield, IL: 3 hrs. 14mins. approx.
Springfield, IL- St. Louis: 1 hr. 28 mins. approx.
St. Louis- Springfield, MO: 3 hrs. 22 mins. approx.
Springfield, MO- Tulsa: 3 hrs approx.
Tulsa - Oklahoma City: 1 hr 34 mins. approx.
Oklahoma City - Amarillo: 4 hrs. approx.

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Chicago and the Quad Cities (Self Drive)

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This self-drive, independent vacation package will introduce you to these beautiful cities through Illinois. Combine Chicago (The wind city will blow you away with its steely skyscrapers, museums and rocking festivals) and Quad Cities (a region of five cities in the U.S. states of Iowa and Illinois: Davenport and Bettendorf in southeastern Iowa, and Rock Island, Moline, and East Moline in northwestern Illinois); with a Rental Car. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Included:

Rental Car for 6 days
Hotel for 3 nights in Chicago
Hotel for 2 nights in Quad Cities
Driving Time
Chicago - Quad Cities: 2 hrs. 51 mins. approx.

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Chicago, IL Vacation Packages

Best Chicago, IL Vacation Packages:

Chicago and the Lake Michigan Shore (Self Drive)

7 nights from $1,351*

Other Chicago, IL Vacation Packages:

Chicago

Hotels and Activities

SUGGESTED Chicago, IL VACATION PACKAGES:

CUSTOMER REVIEWS

Cities in United States