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

7 to 10+ Nights from $1,209*
* This sample price: priced within the past 7 days for arrival on 7/16/2024, departure from New York City NYC (All Airports) (NY), US. Choose your own departure city and dates.

This 7 night sample itinerary includes:

  • Flight into Chicago and out of Oklahoma
  • 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.

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.

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Flexible Itinerary

  • Chicago, IL

  • St Louis, MO

  • Springfield, MO

  • Oklahoma City, OK

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Price Guidance

The package rates displayed are your total price per person based on Double Occupancy and your Arrival Date and Number of Nights selected. You can change details after selecting your travel date.

Price history for this itinerary (past 7 days):

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Chicago, IL
St Louis, MO
Springfield, MO
Oklahoma City, OK
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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.

  • 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.

  • 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.