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Chicago, Il Packages

18 Itineraries
  • View of Chicago Getaway

    Chicago Getaway

    4 to 6+ nights from

    This packages is recommended for 4 to 6+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    $479*

    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. What Makes Tripmasters Vacation Packages Different?Unique, fully custom approach to vacation planningChoose your pre ...

  • View of Chicago and Milwaukee Getaway by Train

    Chicago and Milwaukee Getaway by Train

    5 to 7+ nights from

    This packages is recommended for 5 to 7+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    $513*

    So let's bask in the glow of Illinois and Wisconsin best cities!. An adventurous train ride from Chicago (The wind city will blow you away with its steely skyscrapers, museums and rocking festivals) and Milwaukee (with its acclaimed breweries, the Major League Brewers, and birthplace of the esteemed American motorcycle manufacturer, Harl ...

  • View of Milwaukee and Chicago Getaway by Train

    Milwaukee and Chicago Getaway by Train

    5 to 7+ nights from

    This packages is recommended for 5 to 7+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    $535*

    Let us appreciate the excellence of the top cities in Illinois and Wisconsin!. Embark on an exciting train journey from Milwaukee (with its acclaimed breweries, the Major League Brewers, and birthplace of the esteemed American motorcycle manufacturer, Harley-Davidson) to Chicago (The wind city will blow you away with its steely skyscraper ...

  • View of Detroit and Chicago Getaway by Train

    Detroit and Chicago Getaway by Train

    5 to 7+ nights from

    This packages is recommended for 5 to 7+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    $536*

    Travel by train trough Michigan and Illinois. Explore the wonders of Detroit (best known as the center of the U.S. automobile industry: General Motors, Ford, and Fiat Chrysler are all headquartered there. Its also the birthplace of Motown Records) and Chicago (The wind city will blow you away with its steely skyscrapers, museums and rocki ...

  • View of Chicago and Detroit Getaway by Train

    Chicago and Detroit Getaway by Train

    5 to 7+ nights from

    This packages is recommended for 5 to 7+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    $571*

    How about exploring the amazing cities in Ilinois and Michigan by train?. It's a fantastic opportunity to soak in the vibrant atmosphere and experience the unique charms of Chicago (The wind city will blow you away with its steely skyscrapers, museums and rocking festivals) and Detroit (best known as the center of the U.S. automobile indu ...

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  • View of Chicago and Indianapolis (Self Drive)

    Chicago and Indianapolis (Self Drive)

    6 to 9+ nights from

    This packages is recommended for 6 to 9+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    $780*

    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 (th ...

  • View of Chicago and St. Louis (Self Drive)

    Chicago and St. Louis (Self Drive)

    6 to 9+ nights from

    This packages is recommended for 6 to 9+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    $1,412*

    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 i ...

  • View of Chicago and Indiana Dunes State Park (Self Drive)

    Chicago and Indiana Dunes State Park (Self Drive)

    6 to 9+ nights from

    This packages is recommended for 6 to 9+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    $1,472*

    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 ...

  • View of Chicago and the Lake Michigan Shore (Self Drive)

    Chicago and the Lake Michigan Shore (Self Drive)

    7 to 11+ nights from

    This packages is recommended for 7 to 11+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    $1,519*

    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 ...

  • View of Chicago and Illinois State Beach (Self Drive)

    Chicago and Illinois State Beach (Self Drive)

    6 to 9+ nights from

    This packages is recommended for 6 to 9+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    $1,522*

    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 Harb ...

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

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

    7 to 11+ nights from

    This packages is recommended for 7 to 11+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    $1,691*

    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 ...

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

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

    8 to 12+ nights from

    This packages is recommended for 8 to 12+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    $1,835*

    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 interesti ...

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

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

    15 to 23+ nights from

    This packages is recommended for 15 to 23+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    $2,951*

    Explore iconic Route 66 on a long ride from east to west, venturing through Illinois, Missouri, Oklahoma, and Texas!. Combine Chicago (set on beautiful Lake Michigan, well regarded for interesting architecture - like the Sears Tower - and its cultural highlights from museums to theaters and more), Springfield, Illinois (home of President ...

  • View of Chicago and Rockford (Self Drive)

    Chicago and Rockford (Self Drive)

    4 to 6+ nights

    This packages is recommended for 4 to 6+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    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 Rockford ("The Forest City"; with ...

  • View of Chicago and Lake Peoria (Self Drive)

    Chicago and Lake Peoria (Self Drive)

    5 to 7+ nights

    This packages is recommended for 5 to 7+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    Venture through the fantastic Illinois with your own rental car. Visit Chicago (On Lake Michigan in Illinois, known for interesting architecture like the Sears Tower), then, continue to your next destination, the small city charm of Peoria (the county seat of Peoria County, Illinois, and the largest city on the Illinois River, giving its ...

  • View of Chicago and Naperville (Self Drive)

    Chicago and Naperville (Self Drive)

    5 to 7+ nights

    This packages is recommended for 5 to 7+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    Enjoy this Self-Drive Package to venture through the "Land of Lincoln'; Illinois, discovering these two charming cities. With a Rental Car, combine and visit; Chicago (renowned for its bold architecture, like the "Sears Tower", museums and festivals). After that, have a wonderful stay in Naperville; with an "expected beach surprise": The ...

  • View of Chicago and the Quad Cities (Self Drive)

    Chicago and the Quad Cities (Self Drive)

    5 to 7+ nights

    This packages is recommended for 5 to 7+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    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 southeaster ...

  • View of St. Louis and Chicago (Self Drive)

    St. Louis and Chicago (Self Drive)

    7 to 11+ nights

    This packages is recommended for 7 to 11+ nights.

    Customize it by selecting dates, No. of nights in each city and your departure city.

    Venture through these beautiful cities of Illinois and Missouri, exploring its natural landscapes and nightlife with a rental car. Combine St Louis (offering a 630 ft. Gateway Arch that pays homage to Thomas Jefferson and St. Louis`s position as the getaway to the West) and Chicago (the -Wind City- will blow you away with its steely skycr ...