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Route 66 - Illinois to Oklahoma the Highlights (Self Drive)
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7 to 11+ Nights from $729*
This sample price: priced within the past 7 days for arrival on Saturday, January 30, 2021, departure from New York City (all Airports), NY. Choose your own departure city and dates.
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This is a suggested independent itinerary that you customize. Please select the best flights, hotels, trains, activities, transportation and number of nights in each destination to fit your needs.
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 (known for 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.

This 7 night sample itinerary includes:
  • Flight into Chicago and out of Oklahoma City
  • 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.


Price history for this itinerary (past 7 days):
no image From Amarillo AMA (TX), US for 7 nights
$789 * incl.tax
no image From New York City (all Airports), NY for 7 nights
$736 * incl.tax
no image From STEWART INTERNATIONAL for 7 nights
$742 * incl.tax
Related Cities:
St Louis, MO (11)   Oklahoma City, OK (8)   Springfield, MO (6)   Chicago, IL (13)  
Customize and Book
With Int'l Flight     Without Int'l Flight
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Cabin:
Destination no image
Arrival date
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1. Chicago, IL
   (145 hotels)
2. St Louis, MO
   (24 hotels)
3. Springfield, MO
   (29 hotels)
4. Oklahoma City, OK
   (106 hotels)
Guest:
Please contact us for any special arrangements such as more than three rooms and partial stays.
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Trip Summary
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3 nights in 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.

Recommended Stay: At least 2 nights
Must See`s:
Millenium Park, Willis Tower, Navy Pier, Shedd Aquarium, Grant Park, Cloud Gate, Field Museum, Chicago Riverwalk and much more.


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1 nights in 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.

Recommended Stay: At least 2 nights
Must See`s:
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.


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1 nights in 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.

Recommended Stay: At least 2 nights
Must See`s:
Doling Park, Fellows Lake, Lake Springfield, Sequiota Park, Smallin Civil War Cave, Springfield Conservation Nature Center, Ozark Park Trail, Fantastic Caverns and much more.


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2 nights in Oklahoma City, OK

Oklahoma City is the capital of the U.S. state 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.

Recommended Stay: At least 2 nights
Must See`s:
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.



Book This Package
Flexible Itinerary
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Chicago, IL
Day 1
Arrive to Chicago, IL
Overnight in Chicago, IL   145 hotels offered
Optional  154 Things to do
Day 2
Overnight in Chicago, IL   145 hotels offered
Optional  154 Things to do
Day 3
Overnight in Chicago, IL   145 hotels offered
Optional  154 Things to do
Day 4
Departing from Chicago, IL
Transportation to next city by: Regional Air
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St Louis, MO
Day 4
Arrive to St Louis, MO
Overnight in St Louis, MO   24 hotels offered
Optional  3 Things to do
Day 5
Departing from St Louis, MO
Transportation to next city by: Regional Air
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Springfield, MO
Day 5
Arrive to Springfield, MO
Overnight in Springfield, MO   29 hotels offered
Day 6
Departing from Springfield, MO
Transportation to next city by: Regional Air
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Oklahoma City, OK
Day 6
Arrive to Oklahoma City, OK
Overnight in Oklahoma City, OK   106 hotels offered
Day 7
Overnight in Oklahoma City, OK   106 hotels offered
Day 8
Departing from Oklahoma City, OK

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Chicago, IL Hotels (145 total)
 
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St Louis, MO Hotels (24 total)
 
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Springfield, MO Hotels (29 total)
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Oklahoma City, OK Hotels (106 total)
 

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Tours in Chicago, IL (154 total)
 
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Tours in St Louis, MO (3 total)
 

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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 Night selected. You can change details after selectig your travel date.

Price history for this itinerary (past 7 days):

Your Preferred Major Airport:

*Sample prices on display include ALL taxes & fuel surcharges... read more
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Route 66 - Illinois to Oklahoma the Highlights (Self Drive)
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Photos
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Map
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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.

Recommended Stay: At least 2 nights
Must See`s:
Millenium Park, Willis Tower, Navy Pier, Shedd Aquarium, Grant Park, Cloud Gate, Field Museum, Chicago Riverwalk and much more.
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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.

Recommended Stay: At least 2 nights
Must See`s:
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.
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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.

Recommended Stay: At least 2 nights
Must See`s:
Doling Park, Fellows Lake, Lake Springfield, Sequiota Park, Smallin Civil War Cave, Springfield Conservation Nature Center, Ozark Park Trail, Fantastic Caverns and much more.
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Oklahoma City, OK
Oklahoma City is the capital of the U.S. state 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.

Recommended Stay: At least 2 nights
Must See`s:
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.

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* Sample prices displayed include international and domestic airline tickets as per itinerary and ALL airline-related taxes and fuel surcharges and are per person, based on double occupancy, and are dynamic in nature. Prices do not include insurance or delivery charges which are optional and customizable by the traveler. The airfare portion of the itinerary price is based on economy class, midweek departure. Prices do not include fees for carry on or checked baggage which can add additional fees per ticket on a roundtrip flight based on carrier charges. It also does not include any entrance fees or visa fees that may be charged at international airports. Some cities may charge local taxes that can only be collected by hotel at destination.
Prices were accurate at the time we posted them. Sample prices were for a specific travel date and specific departure airport, as indicated. Your prices will vary according to departure cities and travel dates. We do not control prices (airlines and hotel reservation systems do). Prices may change dynamically and at times significantly numerous times during any given day.

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Important: Many destinations may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories before you book any destination.

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Page, AZ, Lake Superior Shore, MN, Lake Tahoe, CA, Lake Winnebago, WI, Lancaster, PA, Las Cruces, NM, Lawton, OK, Leavenworth, WA, Lenox, MA, Lewis and Clark Wine Valley, ID, Lexington, KY, Lincoln City, OR, Lincoln, NE, Lincoln, NH, Little Rock, AR, Long Beach, CA, Los Alamos, NM, Louisville, KY, Ludlow, VT, Lynchburg, VA, Mackinac Straits, MI, Macon, GA, Madison, WI, Mammoth Lakes, CA, Manchester, NH, Manchester, VT, Mankato, MN, Marblehead, MA, Marietta, GA, Martha`s Vineyard, MA, Mason City, IA, Memphis, TN, Mendocino County, CA, Middlesex County, CT, Milwaukee, WI, Minneapolis-Saint Paul, MN, Minot, ND, Missoula, MT, Mobile, AL, Monterey, CA, Montgomery, AL, Monument Valley, UT, Morgantown, WV, Morro Bay, CA, Mount Pleasant, SC, Mt. Rushmore (Keystone), SD, Murfreesboro, TN, Myrtle Beach, SC, Mystic, CT, Nantucket, MA, Napa Valley, CA, Naperville, IL, Naples, FL, Nashville, TN, Natchez, MS, Nevada City, CA, New Bedford, MA, New Castle, DE, New Haven, CT, New London, CT, New Orleans, LA, Newark, DE, Newark, NJ, Newburyport, MA, Newport Beach, CA, Newport News, VA, Newport, OR, Newport, RI, Niagara Falls, NY, Norfolk, VA, North Conway, NH, North Platte, NE, Northampton, MA, Oakland, CA, Ocean City, MD, Ojai, CA, Oklahoma City, OK, Okoboji Lake, IA, Olympia, WA, Olympic National Park, WA, Omaha, NE, Orlando, FL, Ouray, CO, Outer Banks, NC, Oxford, MS, Palm Desert, CA, Palm Springs, CA, Panama City Beach, FL, Paso Robles, CA, Penn Yan, NY, Pensacola, FL, Peoria, IL, Petrified Forest National Park, AZ, Philadelphia, PA, Phoenix, AZ, Pigeon Forge, TN, Pismo Beach, CA, Pittsburgh, PA, Pittsfield, MA, Plymouth, MA, Pocono Mountains, PA, Point of Rocks, WY, Port Angeles, WA, Port Townsend, WA, Portland, ME, Portland, OR, Portsmouth, NH, Portsmouth, VA, Poughkeepsie, NY, Providence, RI, Provincetown, MA, Pueblo, CO, Quad Cities, IL, Raleigh, NC, Rapid City, SD, Raton Pass, NM, Rehoboth Beach, DE, Reno, NV, Richmond, VA, Roanoke, VA, Rochester, MN, Rochester, NY, Rockford, IL, Rockport, MA, Ruidoso, NM, Sacramento, CA, Salem, MA, Salem, OR, Salt Lake City, UT, San Antonio, TX, San Bernardino Mountains, CA, San Clemente, CA, San Diego, CA, San Jose, CA, San Juan, PR, San Luis Obispo, CA, San Simeon, CA, Sandusky Bay, OH, Sanibel Island, FL, Santa Barbara, CA, Santa Catalina Island, CA, Santa Cruz, CA, Santa Fe, NM, Santa Maria, CA, Santa Rosa, CA, Santa Ynez, CA, Sarasota, FL, Saratoga Springs, NY, Sausalito, CA, Savannah, GA, Scottsdale, AZ, Scranton, PA, Seattle, WA, Sedona, AZ, Seneca Falls, NY, Sequim, WA, Sequoia and Kings Canyon National Park, CA, Shakopee, MN, Sheffield, MA, Sioux City, IA, Sioux Falls, SD, Sisters, OR, Skaneateles, NY, Solana Beach, CA, Solvang, CA, Sonoma Valley, CA, South Bend, IN, Spokane, WA, Springfield, IL, Springfield, MA, Springfield, MO, St Augustine, FL, St Louis, MO, St Petersburg, FL, Steamboat Springs, CO, Stockbridge, MA, Stowe, VT, Syracuse, NY, Table Rock Lake, MO, Tacoma, WA, Tallahassee, FL, Tampa, FL, Tannersville, NY, Taos, NM, Telluride, CO, Temecula, CA, Terre Haute, IN, Teton Village, WY, The Adirondack Mountains, NY, The Berkshires, MA, The Catskills, NY, The Dalles, OR, The Hamptons, NY, Titusville, FL, Toledo, OH, Topeka, KS, Traverse City, MI, Trinidad, CA, Trumansburg, NY, Tucson, AZ, Tulsa, OK, Tuscaloosa, AL, Twin Falls, ID, Umatilla National Forest, OR, Vail, CO, Ventura, CA, Vicksburg, MS, Vienna, VA, Vieques Island, PR, Virginia Beach, VA, Washington, DC, Watkins Glen, NY, West Chester, PA, West Palm Beach, FL, West Yellowstone, MT, White Mountain National Park, NH, Wichita, KS, Williamsburg, VA, Williston, ND, Wilmington, DE, Wilmington, NC, Winston-Salem, NC, Winter Park, CO, Wisconsin Dells, WI, Woodstock, VT, Worcester, MA, Yachats, OR, York, PA, Yosemite National Park, CA | Vietnam Vacations: Ho Chi Minh City (Saigon), Hanoi, Hue, Halong bay, Dalat, Danang, Hoi An, Nha Trang, Phu Quoc Island | Zimbabwe Vacations:
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