Estimated reading time: 14 mins
There’s a version of America that only exists along old Route 66, and it’s not the one you get from an interstate. It’s neon signs still buzzing outside diners that never bothered updating their menus, giant fibreglass animals standing guard over petrol stations that stopped selling petrol decades ago, and towns that built their whole identity around a road most people now drive straight past on the motorway. This first stretch, Chicago down to Oklahoma City, is where the whole thing begins, and honestly, it sets the tone for everything that follows.
I’ve driven a fair bit of Route 66 now, and this opening leg is the one I’d send a first-timer on. You get the flat cornfields of Illinois giving way to the Ozark hills of Missouri, then the road tips you into Oklahoma’s red dirt and big open sky. Along the way there’s a giant blue whale, a genuinely moving arch, a round barn that shouldn’t structurally work but does, and more mom-and-pop diners than you could eat your way through in a month. Five days is enough to do it properly without turning every day into a slog.
This isn’t a trip you rush. Sure, you could drive Chicago to Oklahoma City in a day and a half if you had somewhere to be. But that misses the point entirely, which is stopping at the weird stuff, chatting to the people who’ve kept these little museums and diners going out of pure stubbornness, and letting the road slow you down a bit. It suits couples, road trip veterans, and honestly anyone with a soft spot for Americana who doesn’t mind a bit of kitsch.
You’ll need your own car for this one, no way around it. Most of the good bits sit just off the interstate on the old alignment, and public transport out here is basically nonexistent. I’d sort your hire car in Chicago before you land so you’re not stuck comparing options at the airport counter. If you want more ideas for stringing together an American road trip once this one’s done, our destinations page has plenty to dig through.
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Route 66 Road Trip: Quick Facts at a Glance
- Start: Chicago, Illinois
- End: Oklahoma City, Oklahoma
- Best length: 5 days (6 if you want to properly linger in St. Louis or Tulsa)
- Total distance: Around 850 miles (roughly 1,370 km)
- Best for: Road trip lovers, Americana fans, couples, anyone who likes a good roadside oddity
- Driving difficulty: Easy. Mostly flat, well-signed, with a few sections where the old alignment gets fiddly to follow
- Best time to go: Late spring or early autumn, when the heat's manageable and most attractions are open full hours
- Car needed: Yes, completely essential. This trip does not work without one
- Main route: Chicago → Pontiac → Springfield, IL → St. Louis → Rolla → Springfield, MO → Joplin → Galena → Catoosa → Tulsa → Arcadia → Oklahoma City
Sort your hire car first: This whole trip lives or dies on having your own set of wheels, so it's worth locking one in early rather than scrambling at Chicago O'Hare. Compare hire car options in Chicago and grab something with decent boot space, because you'll want room for whatever roadside souvenirs find their way into the car.
The Route: What to Expect
The shape of this one is refreshingly simple. You start in Chicago and just keep heading south-west, following the old Route 66 alignment wherever it survives and hopping onto the interstate for the dull connector bits. No loops, no backtracking, no faff. Illinois gives you flat farmland and small-town Americana, Missouri throws in some genuine hills and the Gateway Arch, and Oklahoma finishes things off with wide-open plains and a proper skyline in Tulsa.
Five days breaks down into five solid driving legs, each landing you somewhere worth spending the evening. None of the days are brutal, the longest is around four hours behind the wheel, but you’ll want to build in stop time because that’s honestly the whole point of this drive. Rush it and you might as well have flown.
| Day | Route | Drive time | Vibe |
|---|---|---|---|
| 1 | Chicago → Pontiac → Springfield, IL | ~4 hrs | Neon signs, Lincoln country |
| 2 | Springfield, IL → St. Louis → Rolla | ~4 hrs | Big city arch, roadside kitsch |
| 3 | Rolla → Springfield, MO → Joplin | ~3.5 hrs | Ozark curves, ghost towns |
| 4 | Joplin → Galena → Catoosa → Tulsa | ~3 hrs | Three states, one Blue Whale |
| 5 | Tulsa → Arcadia → Oklahoma City | ~2 hrs | Round barn to finish line |
Note: FREE Google Map Lower Down the Article.
Route 66 Road Trip Itinerary
Day 1: Chicago → Pontiac → Springfield, IL
Driving: Pontiac is about 100 miles from Chicago (roughly 1 hr 45). Springfield is another 90 miles on (about 1 hr 30). Call it a 190 mile day, closer to 4 hours once you factor in stops.
Route 66 technically starts at the corner of Adams Street and Michigan Avenue in Chicago, and there’s something oddly moving about standing next to that little brown sign knowing the road runs 2,400 miles from where you’re stood. Get out of the city early, because Chicago traffic doesn’t care that you’re on a nostalgic road trip. Pontiac is your first real stop, home to one of the best Route 66 museums on the whole route and a downtown absolutely covered in murals dedicated to the road. From there it’s a straight run down to Springfield, Abraham Lincoln’s old stomping ground and also, more importantly for this trip, the birthplace of the corn dog.
Things to do:
- Snap a photo at the official Route 66 start sign on Adams Street before you leave Chicago
- Stop in Pontiac for the Route 66 Hall of Fame and Museum (allow an hour, the murals alone are worth the detour)
- Wander Springfield’s Lincoln sites if history’s your thing, the Old State Capitol is a highlight
- Eat dinner at the Cozy Dog Drive In, the actual birthplace of the corn dog on a stick
Timing tip: Give yourself extra time getting out of Chicago itself. Rush hour on the way south out of the city can add a genuinely painful chunk to your morning, so aim to be rolling by 9am if you can manage it.
Where to Stay in Springfield
Day 2: Springfield, IL → St. Louis → Rolla
Driving: St. Louis is about 100 miles from Springfield (roughly 1 hr 45). Rolla is another 100 miles past that (about 1 hr 30). Roughly 200 miles total, closer to 4 hours with stops.
This is the day the trip properly earns its keep. St. Louis brings the Gateway Arch, which somehow manages to be more impressive in person than in any photo you’ve seen of it, curving 630 feet into the sky right on the banks of the Mississippi. It’s worth the tram ride to the top if you don’t mind a slightly cramped capsule, the view over the river and the city is genuinely something. After St. Louis, the road takes you into properly kitsch Route 66 territory, with a stop at Route 66 State Park and the wonderfully strange Meramec Caverns, a cave system that’s been a tourist attraction since long before that was a normal thing to be.
Things to do:
- Ride the tram to the top of the Gateway Arch (book ahead, it sells out on busy days)
- Grab lunch in St. Louis, toasted ravioli is the local speciality worth hunting down
- Stop at Meramec Caverns for a proper underground tour, allow around an hour and a half
- Look out for the classic barn adverts painted along the highway, a Route 66 institution
Must do: Book your Gateway Arch tram tickets online before you arrive. Walk-up tickets exist but the queue can eat well over an hour of your afternoon, and that's time you'd rather spend at Meramec Caverns.
Recommended read: USA Travel Tips For First-Timers: Your Fun, Foolproof Guide
Where to Stay in Rolla
Day 3: Rolla → Springfield, MO → Joplin
Driving: Springfield, MO is about 100 miles from Rolla (roughly 1 hr 45). Joplin is another 75 miles on (about 1 hr 15). Around 175 miles total, close to 3.5 hours with a couple of stops.
This is the day the road gets genuinely pretty. You’re deep into the Ozarks now, and the old alignment twists through hills and past a stretch called the Devil’s Elbow, a sharp bend over the Big Piney River that loggers apparently swore about constantly, hence the name. Springfield, Missouri claims the title of Route 66’s actual birthplace, which the Illinois Springfield might dispute, but either way it’s a decent lunch stop. Further on you’ll pass through a string of tiny towns that peaked in the 1950s and have been quietly fading ever since, which sounds sad written down but is oddly charming in person. Joplin is your stop for the night, right on the edge of Missouri.
Things to do:
- Detour to Devil’s Elbow and walk the old bridge over the Big Piney River
- Stop in Springfield, MO for lunch and a look at the Route 66 birthplace marker
- Pull over at Gary’s Gay Parita, a lovingly restored replica of a 1930s filling station
- Wander Joplin’s small downtown before calling it a night
Watch out: Phone signal drops out completely in stretches of the Ozarks, and the old alignment isn't always well signed once you leave the interstate. Download offline maps for this section before you set off, not after you're already lost.
Recommended reads: All Guides to the USA
Where to Stay in Joplin
Day 4: Joplin → Galena → Catoosa → Tulsa
Driving: Galena is about 10 miles from Joplin (roughly 15 minutes). Catoosa is another 100 miles on (about 1 hr 40). Tulsa is a final 20 miles past that (about 25 minutes). Around 130 miles total, but expect close to 3 hours once you factor in three states and a very slow drive-by of a giant whale.
This might be the best day of the whole trip, purely because you knock out three states before lunch. Galena, Kansas sits right at the start, a tiny town that’s basically Route 66 royalty since it’s the reported inspiration for the town of Radiator Springs in the film Cars. There’s a rusted old tow truck parked there that genuinely looks like it wandered off a film set. From Galena it’s a short hop into Oklahoma, where the road delivers its most photographed roadside attraction: the Blue Whale of Catoosa, a genuinely enormous concrete whale sitting in a pond that a man built for his wife back in the 1970s because, well, why not. Tulsa rounds out the day with proper Art Deco architecture and a skyline that catches you off guard after days of small towns.
Things to do:
- Snap a photo with the old tow truck in Galena, Kansas (the whole detour takes maybe 20 minutes)
- Cross into Oklahoma and pull over at the Blue Whale of Catoosa, walk out onto the pier for the full effect
- Wander Tulsa’s Art Deco district, the Boston Avenue Methodist Church is a standout
- Catch the Cyrus Avery Route 66 Memorial where the old road crosses the Arkansas River
Fact: Route 66 was one of the original federal highways designated in 1926, running from Chicago to Santa Monica. Tulsa businessman Cyrus Avery pushed hard for the route to run through Oklahoma, which is why the city calls itself the Birthplace of Route 66.
Where to Stay in Tulsa
Day 5: Tulsa → Arcadia → Oklahoma City (finish line)
Driving: Arcadia is about 85 miles from Tulsa (roughly 1 hr 30). Oklahoma City is a final 20 miles on (about 25 minutes). Around 105 miles total, a gentle finish at just under 2 hours.
The last day is a short, easy drive, which is exactly what you want after four days of Americana overload. Arcadia is the standout stop, home to the Round Barn, a genuinely strange piece of 1898 engineering that’s somehow still standing despite every logical reason it shouldn’t be, and just down the road is Pops 66, a soda ranch with a 66 foot tall neon soda bottle out front and more flavours of pop than seems reasonable. From there it’s a short run into Oklahoma City, your finish line, where the Oklahoma City National Memorial makes for a properly reflective way to end the trip before you toast the finish somewhere in the Bricktown district.
Things to do:
- Tour the Round Barn in Arcadia and appreciate that it’s still standing (allow 20 minutes)
- Stop at Pops 66 for a novelty soda and a photo with the giant bottle
- Visit the Oklahoma City National Memorial, give it proper time rather than rushing through
- Celebrate the finish with dinner in Bricktown, right by the canal
Quick win: Pops 66 gets busy with tour buses around midday. Swing by mid-afternoon instead and you'll get the giant bottle photo without twenty other people in the shot.
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Where To Stay For This Route 66 Road Trip
Accommodation along this stretch is a mix of proper cities and genuinely tiny towns, so where you sleep changes flavour every night. Stick close to the old alignment where you can, since that’s where the character is, and don’t expect much beyond the essentials in the smaller stops.
Springfield, IL (night 1): Stay downtown near the Lincoln sites if you want to walk to dinner, or pick a motel along the old Route 66 alignment for a slice of the road itself. Either works for one night.
Rolla (night 2): Options here are mostly practical motels rather than boutique stays. Pick somewhere on the east side of town so you’re already pointed the right way for tomorrow’s drive into the Ozarks.
Joplin (night 3): A few decent mid-range chains cluster near the centre. Nothing fancy, but comfortable, and you’ll be glad of a proper bed after the Devil’s Elbow detour.
Tulsa (night 4): Worth spending slightly more here. The downtown Art Deco district has some genuinely characterful hotels housed in old buildings, and it puts you walking distance from dinner.
Oklahoma City (your finish, night 5): Base yourself in Bricktown for the canal, the restaurants, and an easy walk back after a celebratory drink. It’s the liveliest part of the city and a fitting spot to end five days on the road.
For browsing specific properties along the route, Booking.com and Hotels.com both cover these towns well, and Expedia is worth a look if you want to bundle a couple of nights together.
Pit Stops & Side Detours
The main route already links up nicely, but there are a handful of easy add-ons if you’ve got a spare half-day or want to stretch this into six. Keep them short and slot them into the nearest driving day rather than treating them as separate trips.
- Funks Grove, a family-run sorghum farm south of Bloomington that’s been making syrup since the 1800s
- The Chain of Rocks Bridge just outside St. Louis, an old Mississippi crossing with a striking bend halfway across, now closed to cars and open for walking
- Elbow Inn Bar and BBQ near Devil’s Elbow, an old roadhouse plastered wall to wall in signed dollar bills
- The Precious Moments Chapel near Carthage, an oddly sincere detour if you’re curious about it
- The Golden Driller statue in Tulsa, a 76 foot tall oilman standing guard outside the Expo Center
- Skip: the fully signed “historic alignment” through some of the smaller Illinois towns if you’re pushed for time. A few stretches genuinely just parallel the interstate with nothing to see, and you can rejoin further on without missing much
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Browse the shopLocal Eats Worth Chasing
This route is basically a diner crawl with some driving attached, and I mean that as a genuine compliment. Come hungry, and don’t be precious about the decor.
- Corn dogs at the Cozy Dog Drive In in Springfield, IL, the place that invented them and never stopped serving them
- Toasted ravioli in St. Louis, a deep-fried bar snack that St. Louis takes weirdly seriously and rightly so
- Fried pie at any roadside stand that’s still selling them, they’re becoming rarer every year
- Barbecue in Joplin or Tulsa, both towns take their smoked meat seriously and neither will let you down
- Novelty soda at Pops 66 in Arcadia, pick something you’ve never heard of over your usual order
- Chicken fried steak once you hit Oklahoma, it’s basically mandatory at this point in the trip
Road Trip Playlist
Podcasts to Queue Up
There’s a fair bit of flat, quiet highway between the good bits, especially through Illinois and Kansas. Load a few of these up before you lose signal.
- A history podcast covering the Dust Bowl or the Great Migration, both of which shaped this exact stretch of America
- Something on the building of the interstate system, which is essentially the story of why Route 66 nearly disappeared
- A long-form true crime series for the featureless bits of Missouri and Kansas
- A music history episode on the blues, since you’re tracking roughly parallel to where a lot of it was born
- An audiobook saved specifically for the Joplin to Tulsa stretch, which is your quietest driving day
Quick win: Download the playlist. Use zero data, and you dont need to worry about signal!
Road Trip Essentials
Nothing complicated here, but a few things genuinely make this trip smoother, and I learned some of them the annoying way.
A hire car with decent range. Petrol stations thin out on some of the old alignment stretches, so don’t run the tank down to fumes hoping the next town has a station. I’d sort your hire car through DiscoverCars before you land in Chicago, comparing options early tends to land you a better price and a car that isn’t running on empty warning lights by day three.
Offline maps, downloaded properly. Signal drops out through the Ozarks and parts of rural Kansas, exactly where the old alignment gets trickiest to follow. Download Illinois, Missouri, Kansas and Oklahoma on Google Maps the night before you leave Chicago.
A physical Route 66 guidebook or map. Sounds old-fashioned, but the old alignment isn’t always in your GPS, and paper doesn’t care about signal. Most Route 66 museums along the way sell a decent one for a few dollars.
Travel insurance, because road trips invite plot twists. A flat tyre, a missed connection, a stomach that regrets the third corn dog of the day. Worth having travel insurance sorted through VisitorsCoverage before you set off rather than hoping for the best.
Cash for the smaller attractions. A lot of the roadside museums and diners along this route are family-run and still cash-preferred, especially in the tinier towns. Keep a stash in the glovebox so you’re not stuck at a card machine that doesn’t exist.
A working eSIM if you’re flying in from abroad. US roaming plans can get pricey fast, and you’ll want data for maps and booking confirmations the whole way. Grab a Holafly eSIM before you land and use the code THETRAVELTINKER for 5% off any eSIM, or 10% off Holafly plans for your first 12 months. For a few extra options, Airalo is also worth a look. For more of what I always pack for a trip like this, my travel planning resources page has the full kit list, and there’s more general advice on my travel tips page too.
Stay connected: Signal genuinely comes and goes through the Ozarks and rural stretches of Kansas, so don't rely on constant data for navigation. Sort a Holafly eSIM before you go (code THETRAVELTINKER for 5% off any eSIM, or 10% off Holafly plans for your first 12 months), and pair it with the offline maps mentioned above so you're never fully stuck.
Money saver: Most of the roadside attractions on this route, the Blue Whale, the Round Barn, Gary's Gay Parita, are free or ask for a small donation. Save your budget for the paid stuff that's actually worth it, like the Gateway Arch tram and Meramec Caverns.
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Helen Ross
I’m a 32-year-old photographer and travel enthusiast, journeying from place to place, immortalizing the hidden tales, unseen moments, and the narratives that lie between.
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