Route 66 Eastern Half
Route 66 road trip holiday exploring the Eastern half of Route 66 from Chicago to Oklahoma City
If you want to experience the magic of Route 66 but don’t want to drive the entire distance from Chicago to Los Angeles — or you’d like to split the Mother Road into two separate adventures — this Eastern Half itinerary is ideal. You’ll begin with three nights in Chicago, exploring the Windy City and capturing that essential photo at the “Route 66 Begin” sign, before easing into the classic small-town Americana that makes this road so special. From here, you’ll follow Route 66 through Illinois, Missouri, Kansas and Oklahoma, travelling via mural-filled Pontiac, historic Carthage and neon-signed stretches of 66 on your way to the plains.
Along the way you’ll discover original brick road, vintage diners, old gas stations and legendary roadside attractions like the Blue Whale of Catoosa and the Sidewalk Highway. Your journey finishes in Fort Worth, Texas, where Western heritage, stockyards, live music and great food provide a fitting finale. This is the perfect introduction to Route 66 — or the first half of a future full-route adventure.
Remember: We’re UK-based, and every holiday we create is fully flexible – you can add nights, upgrade hotels, or enhance your itinerary. We love designing tailor-made self-drive adventures just for you!
12 night self drive holiday from £1,999pp including flights, accommodation & car rental
Highlights
Start your journey in Chicago, exploring the Magnificent Mile and iconic skyline views.
Stay in Pontiac and Carthage, two of the most authentic Route 66 towns, famous for murals and Red Oak II.
Drive through four Route 66 states – Illinois, Missouri, Kansas and Oklahoma – packed with diners, motels and classic roadside attractions.
Finish with two nights in Fort Worth, perfectly placed for exploring the Stockyards, Dallas and wider Texas culture.
Your itinerary
DAYs 1-3: ARRIVE and explore CHICAGO
Discover the Windy City’s skyline, culture and Route 66 heritage
Your adventure begins with three memorable nights in Chicago, the vibrant Great Lakes city where Route 66 officially begins. Explore world-famous sights such as the Willis Tower Skydeck, Millennium Park and The Bean, the Art Institute of Chicago and the Riverwalk. An architectural cruise reveals the city’s pioneering skyscraper design and stunning skyline views. Wander the Magnificent Mile’s shops and eateries, sample authentic deep-dish pizza, or enjoy blues and jazz in the very city where these genres built their legends. There’s no better place to ease into your Route 66 journey.
3 Nights in
Chicago, IL
Arrive &
Explore
DAY 4: chicago to PONTIAC
Muffler Men, murals and Illinois’ Route 66 heritage
Collect your hire car and follow historic Route 66 out of Chicago, passing vintage diners and rural farmland before stopping at the Gemini Giant in Wilmington – one of Route 66’s most iconic “Muffler Men.” Continue through charming small towns with restored gas stations and nostalgic roadside stops until you reach Pontiac. Famous for more than 20 colourful outdoor murals, Pontiac is also home to the superb Route 66 Hall of Fame & Museum and Bob Waldmire’s legendary “Road Yacht” bus. With its friendly atmosphere, classic diners and walkable historic centre, Pontiac delivers a wonderfully authentic start to your Mother Road adventure.
1 Night in
Pontiac, IL
100 miles
Day 5: Pontiac to Springfield, Illinois
Lincoln heritage, historic districts and small-town Americana
Drive deeper into the heart of Illinois, passing through Bloomington and the town of Lincoln, each filled with historical courthouses, roadside photo stops and long-standing diners. Your destination is Springfield, a city central to Abraham Lincoln’s early life and American political history. Visit Lincoln’s preserved home, stroll the State Capitol grounds and explore the impressive Lincoln Presidential Library and Museum. Springfield’s Route 66 sites add extra character, with classic neon, historic eateries and a relaxed Midwestern charm that makes this an atmospheric stop on the journey.
1 Night in
Springfield, IL
105 miles
Day 6: Springfield to St Louis
Historic cafés, brick roads and the landmark Gateway Arch
Today’s short but significant drive features some of Illinois’ most treasured Route 66 attractions. You’ll travel the original hand-laid brick pavement in Auburn, then continue to Litchfield for a meal at the Ariston Café — among the oldest continually operating restaurants on Route 66. Cross the Mississippi River on the historic Chain of Rocks Bridge and arrive in St Louis, home of the magnificent Gateway Arch. Ride to the top for incredible river and city views, wander the revitalised riverfront, or discover lively districts filled with blues bars, barbecue restaurants and museums that celebrate the city’s frontier spirit.
1 Night in
St Louis, MO
100 miles
Day 7: St Louis to Springfield, Missouri
Rolling Ozark hills, mural towns and the birthplace of Route 66
Leave urban St Louis behind and head into the scenic Ozark Mountains, where forested hills, gentle curves and classic roadside towns define this beautiful stretch of Route 66. Stop in Cuba, known as the Route 66 Mural City, and in Rolla, home to restored petrol stations and historic diners. Your day ends in Springfield, Missouri — the official birthplace of Route 66, where the highway was first designated in 1926. Visit the Route 66 Car Museum, admire retro neon signs and enjoy the friendly, relaxed energy of this historic destination.
1 Night in
Springfield, MO
215 miles
Day 8: Springfield to Carthage & RED OAK II
Carthage heritage and the nostalgic living museum of Red Oak II
Today’s drive may be short, but it’s rich with vintage Americana. Arrive in Carthage, known for its grand 19th-century courthouse and architecture tied to the early days of Route 66. Just beyond town sits Red Oak II, a unique open-air museum created by artist Lowell Davis. Explore relocated and restored structures — old gas stations, cafés, barns and workshops — arranged to resemble a small mid-century Route 66 town. It’s charming, atmospheric and wonderfully photogenic, offering an immersive window into the Mother Road as it once was.
1 Night in
Carthage, MO
60 miles
Day 9: Carthage to Tulsa
Three states in one day, classic icons and Tulsa’s Art Deco skyline
This is a milestone day: you’ll cross Missouri, Kansas and Oklahoma in a single scenic journey. Kansas’ 13-mile stretch of Route 66 is filled with gems, including Galena’s Kan-O-Tex Station, the historic Rainbow Bridge and small towns that retain their 1930s charm. Continue into Oklahoma to visit the famous Blue Whale of Catoosa, a quirky landmark beloved by travellers. Arrive in Tulsa, a city with a rich Route 66 heritage, glowing neon signage and one of the best collections of Art Deco architecture in the USA. Its lively music, dining and entertainment scene makes it an exciting overnight stop.
1 Night in
Tulsa, OK
130 miles
Day 10: Tulsa to Oklahoma City
Sidewalk Highway, classic diners and Oklahoma’s Western spirit
Continue west on one of the most historically intact stretches of old Route 66. Between Miami and Afton, drive the remarkable “Sidewalk Highway,” an original nine-foot-wide single-lane section that offers a vivid sense of early motoring days. Explore small towns dotted with retro motels, diners and vintage signage before arriving in Oklahoma City. Wander the Bricktown District with its riverside restaurants and live entertainment, or delve into the region’s frontier history at the National Cowboy & Western Heritage Museum. This leg perfectly blends authentic Route 66 heritage with big-city energy.
1 Night in
Oklahoma City, OK
115 miles
Days 11–12: Oklahoma City to Fort Worth, Texas
Cowboy culture, city highlights and a memorable finale in Texas
On your final leg, leave Route 66 behind and head south into Texas for a relaxing two-night stay in Fort Worth — the perfect ending to your shortened Mother Road adventure. This vibrant city blends cattle-drive heritage with a modern arts and dining scene. Explore the famous Stockyards, where longhorn parades, rodeo shows, Western shops and live country music bring the Old West to life. In nearby Dallas you can visit Dealey Plaza and the Sixth Floor Museum for a thoughtful look at JFK history, or spend time in lively Deep Ellum with its murals and music venues.
On your final morning, enjoy a leisurely breakfast or some last-minute shopping before driving to Dallas–Fort Worth International Airport. Drop off your hire car and board your flight back to the UK — heading home with unforgettable memories of your Eastern Half Route 66 adventure.
2 Nights in
Fort Worth, TX
215 miles
May- Jun & Sept- Oct: Weather is likely to be pleasant for the entire trip. The midwest shouldn’t be too cold and the southwestern states shouldn’t be too hot.
We would expect maximum temperatures to be in the 20°C - 30°C range in the midwest and 25°C - 35°C in the south and southwestern states
Flight times to/from Chicago is around 8 hours and Los Angeles is approx 11 hours. You’ll drive through 3 time zones. Chicago is 5 hours and Los Angeles is 8 hours behind the UK.
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