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

15 to 22+ Nights from $2,945*
* This sample price: priced within the past 7 days for arrival on 8/31/2024. Choose your own arrival dates.

Customize and Book

This 15 night sample itinerary includes:

  • 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.

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.

Flexible Itinerary

  • Chicago, IL

  • Springfield, IL

  • St Louis, MO

  • Springfield, MO

  • Tulsa, OK

  • Oklahoma City, OK

  • Amarillo, TX

Customer Reviews

Trip Summary

  • Chicago, IL

    Chicago, on Lake Michigan in Illinois, is among the largest cities in the U.S. 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. The city is also renowned for its museums, including the Art Institute of Chicago with its noted Impressionist and Post-Impressionist works.

    Explore the Millenium Park, Willis Tower, Navy Pier, Shedd Aquarium, Grant Park, Cloud Gate, Field Museum, Chicago Riverwalk and much more.

  • Springfield, IL

    Springfield is the state capital of Illinois. Downtown, the interior of Illinois State Capitol's large dome is decorated with stained glass and statues of historical figures. The 1904 Dana-Thomas House was designed by Frank Lloyd Wright. The Abraham Lincoln Presidential Library and Museum traces the life of the 16th U.S. president. Lincoln's restored home is nearby. North, the Lincoln Tomb lies in Oak Ridge Cemetery.

    Explore the Lincoln Home, Illinois State Museum, Dana Thomas House, Old State Capitol, Henson Robinson Zoo, Knights Action Park, Abraham Lincoln Presidential Library and Museum and much more.

  • St Louis, MO

    St. Louis is a major city in Missouri along the Mississippi River. Its iconic, 630-ft. Gateway Arch, built in the 1960s, honors the early 19th-century explorations of Lewis and Clark and America's westward expansion in general. Replica paddlewheelers ply the river, offering views of the arch. The Soulard district is home to barbecue restaurants and clubs playing blues music.

    Explore The Gateway Arch, Missouri Botanical Garden, Forest Park, Saint Louis Zoo, Saint Louis Science Center, Cahokia Mounds State Historic Site, Tower Grove Park and much more.

  • Springfield, MO

    Springfield is a city in southwestern Missouri. The Discovery Center of Springfield has interactive science exhibits on topics from DNA to dinosaurs. To the north, Dickerson Park Zoo features animals from around the world, plus train rides. Trams run through a cave filled with stalagmites and flowstones at Fantastic Caverns. The Nathanael Greene/Close Memorial Park has trails and botanical gardens.

    Explore the Doling Park, Fellows Lake, Lake Springfield, Sequiota Park, Smallin Civil War Cave, Springfield Conservation Nature Center, Ozark Park Trail, Fantastic Caverns and much more.

  • Tulsa, OK

    Tulsa is a city on the Arkansas River, in the state of Oklahoma. It’s known for its art deco architecture, mostly in the central Deco District. Landmarks like the Philcade and Philtower buildings reflect a 20th-century construction boom fueled by the prosperous local oil industry. The Philbrook Museum of Art is housed in an Italianate villa that was once the home of a local oil magnate.

    Explore the Philbrook Museum of Art, Gilcrease Museum, Oklahoma Aquarium, Tulsa Zoo, Blue Whale of Catoosa, Gathering Place, Oxley Nature Center, Woody Guthrie Center and much more.

  • Oklahoma City, OK

    Oklahoma City is the capital of Oklahoma. It's known for its cowboy culture and capitol complex, surrounded by working oil wells. The reflecting pool and empty glass and bronze chairs of the Oklahoma City National Memorial recall the victims of the 1995 bombing of the Alfred P. Murrah Federal Building. The Survivor Tree, an American elm nearly destroyed in the attack, is also part of the memorial.

    Explore the Oklahoma City Zoo, Myriad Gardens, Bricktown, Frontier City Theme Park, Oklahoma City National Memorial and Museum, National Cowboy and Western Heritage Museum and much more.

  • Amarillo, TX

    Amarillo, nicknamed The Yellow Rose of Texas, is the largest city in the Texas Panhandle. Known as the place to absorb the cowboy and longhorn cattle culture Texas is so famous for. Boasting a great food scene, historic districts and buildings, and eclectic attractions such as the Cadillac Ranch. It is also a great base for exploring Palo Duro Canyon, the second-largest canyon in the United States. Events in town celebrate the life and legend of the cowboy, such as the Tri-State Fair & Rodeo, in operation since 1921, which brings cowboys from all over the United States. Amarillo is fairly low-key and nondescript at first glance, but it is a pleasant, inexpensive spot for an overnight stay.

    Visit the Cadillac Ranch, Palo Duro Canyon State Park, Wonderland Amusement Park, American Quarter Horse Hall of Fame, Panhandle-Plains Historical Museum, Amarillo Zoo, Amarillo Botanical Gardens, Texas Air & Space Museum, Kwahadi Museum of the American Indian, and so much more!

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