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Chicago and St. Louis (Self Drive)
6 nights from
$1,400*
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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).
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Included:
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Chicago and Indiana Dunes State Park (Self Drive)
6 nights from
$1,540*
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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).
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Included:
- Flight into Chicago and out of South Bend
- 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
$1,704*
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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).
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Included:
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Route 66 - Illinois to Texas the Long Ride (Self Drive)
15 nights from
$3,286*
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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 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).
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Included:
- Flight into Chicago and out of Amarillo
- 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)
More details
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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.
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Included:
Close more details