
Cruisin’ Through Missouri – Chicago to Tulsa
From
£1,839pp
Cruisin’ Through Missouri – Chicago to Tulsa
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✓£49pp low deposit followed by 5 monthly Direct Debit payments of £358pp
✓Car hire included
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- Guests: 2 Adults
- Duration: 10 Nights
- Board: Various Board
- Departing: Selected UK Airports
- Offer Date: 1st November 2025
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Hit the open road for an exciting ten-night driving adventure along Route 66 from Chicago to Tulsa. This thrilling self-drive trip along one of the United States’ most famous roadways includes stays in Chicago, St Louis, Cuba, Lebanon, Springfield, Joplin, and Tulsa. You can also look forward to experiencing iconic sights and attractions, admiring beautiful scenery, tasting mouth-watering cuisine, and enjoying vibrant culture.
Day One: Chicago, Illinois
Fly into Chicago where your ten-night Route 66 adventure gets underway when you pick up your car at the airport and drive to Hilton Garden Inn Chicago Downtown Riverwalk for an overnight stay. You’ll have time to explore classic Route 66 sights including Route 66 "Begin" Sign, Lou Mitchell’s Diner (a traditional Route 66 send-off), and The Berghoff Restaurant (historic 66-era spot). You could even visit Willis Tower Skydeck to soak up the amazing citywide views.
Day Two: Chicago to St Louis, Missouri (300 miles, five hours)
Start your Route 66 journey towards St Louis. Suggested stops along the way, include Gemini Giant - classic roadside Muffler Man in Wilmington, Cozy Dog Drive-In - home of the original corn dog in Springfield, and Old Chain of Rocks Bridge - historic Route 66 Mississippi River crossing into St. Louis. Perhaps spend the evening visiting the iconic Gateway Arch and Ted Drewes Frozen Custard. Your home for the next two nights is Drury Inn St Louis at Union Station.
Day Three: St Louis, Missouri
Explore more of St. Louis today. Pay a visit to Missouri History Museum to view the Route 66 exhibits. Follow in the footsteps of famous St Louisans who have changed the city’s culture and history at the St Louis Walk of Fame. Enjoy a stroll in Forest Park or admire the artworks on display at St Louis Art Museum. Or why not get up close to the animals at St Louis Zoo or try the local ales at Anheuser-Busch Brewery?
Day Four: St Louis to Cuba, Missouri (85 miles, 1.5 hours)
Your adventure continues with a drive to Cuba in Missouri – famous for its Route 66 murals. En-route you can visit Route 66 State Park, explore Meramec Caverns - Jesse James’ hideout, and see Fanning 66 Outpost and a 42-foot tall Rocking Chair. Look forward to an overnight stay at the Super 8 by Wyndham in Cuba.
Day Five: Cuba to Lebanon, Missouri (80 miles, 1.5 hours)
Today’s road trip takes you to Lebanon in Missouri. En-route you’ll have time to visit one of Route 66’s oldest motels – Cuba’s Wagon Wheel Motel and make a stop at Uranus Fudge Factory for a quirky roadside experience. On arrival in Lebanon, you can tour the Route 66 Museum before checking into Hampton Inn Lebanon for an overnight stay.
Day Six – Lebanon to Springfield, Missouri (55 miles, 1 hour)
Get back behind the wheel and make your way to Springfield in Missouri. Springfield is your gateway to exploring the Route 66 Car Museum, checking out the historic Gillioz Theatre, and visiting Rockwood Motor Court & Best Western Rail Haven - where Elvis Presley stayed! Your home for the next two nights is Springfield’s Best Western Route 66 Rail Haven.
Day Seven: Springfield, Missouri
Your exploration of Springfield continues today. You’ll have time to visit the Route 66 Springfield Visitor Center and learn more about the Birthplace of Route 66. Tour the History Museum on the Square and dine at local diners along the Mother Road.
Day Eight: Springfield to Joplin, Missouri (60 miles, 1 hour)
Your travels today take you to Joplin in Missouri. Make a stop enroute at Gary’s Gay Parita, a restored 1930s gas station and pay a visit to the 66 Drive-In Theatre. Explore Red Oak II, a recreated 1930s ghost town, and admire the amazing Grand Falls, Missouri’s largest continuously flowing waterfall. Your resting place for the next two nights is Homewood Suites by Hilton Joplin.
Day Nine: Joplin, Missouri
You have more time to explore Joplin today including its Route 66 sights. Wander through Route 66 Mural Park to gaze at the two large tile murals: Cruisin’ into Joplin and The American Ribbon and take a stroll through the past at Bonnie and Clyde’s Joplin Hideout.
Day Ten: Joplin to Tulsa, Oklahoma (115 miles, two hours)
Today’s drive takes you to your final destination of Tulsa in Oklahoma for a night’s stay at Residence Inn Tulsa Downtown. Seek out Tulsa’s Route 66 Rising Monument in the Avery Traffic Circle and also the iconic Meadow Gold Sign in the Meadow Gold District. Take the chance to explore Tulsa’s Route 66 sights, such as The Golden Driller, The Blue Dome District, Cyrus Avery Route 66 Memorial Bridge, and Philbrook Museum of Art.
Day Eleven: Tulsa to the UK
Check out of your hotel and drive to Tulsa International Airport in time for your flight back to London Heathrow via Los Angeles – hopefully with many happy memories to look back on of your Chicago to Tulsa fly drive adventure.
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