Driving Route 66: Chicago to Texas

Chicago to Texas: An October journey

Driving Route 66 from Chicago to Texas in October felt like hitting the road at exactly the right moment. The air was crisp, the crowds had thinned, and the scenery seemed made for slowing down. This stretch of the Mother Road gave me everything I hoped for—neon nostalgia, small-town charm, historic landmarks, and those long, open landscapes that let your thoughts wander as easily as the road itself.

All the states that Route 66 passes through

Why October worked so well

October turned out to be one of the best times I could have chosen for this drive. Days were comfortable across Illinois, Missouri, Oklahoma, and Texas, and the cooler temperatures made long hours behind the wheel enjoyable. Parking was easy, museums were quiet, and I never felt rushed. In Illinois and Missouri, fall colors lit up the countryside, while the Texas Panhandle stayed cool enough to explore without the summer heat bearing down.

Me at one of the many restored stations along the way

Trip highlights by region

• Chicago to Southern Illinois
  I kicked things off at the iconic “Begin Route 66” sign in downtown Chicago—one of those moments that instantly makes the journey feel real. From there, I settled into classic stops like Lou Mitchell’s Diner, the Gemini Giant in Wilmington, and the mural-filled streets of Pontiac. The farmland and small towns glowed with autumn color, giving this stretch a warm, almost nostalgic calm.

• Missouri: St. Louis to Joplin
  Missouri surprised me in the best way. Rolling hills looked even better dressed in fall foliage, and the history felt especially present. I made time for the Chain of Rocks Bridge, Ted Drewes Frozen Custard, the Wagon Wheel Motel in Cuba, and the Route 66 Museum in Lebanon. As evening set in, the neon signs came alive, turning quiet nights into some of my favorite photo moments of the trip.

• Oklahoma: The longest driveable stretch
  Oklahoma felt like the heart of Route 66. With more original road here than anywhere else, it was easy to imagine decades of travelers passing through. Stops like the Blue Whale of Catoosa, Pops Soda Ranch, the Round Barn in Arcadia, and the National Route 66 Museum in Elk City gave the drive both whimsy and depth. October brought perfect road-trip weather and, in some towns, local festivals that made the experience feel even more authentic.

The Blue Whale

• Texas Panhandle: Shamrock to Amarillo
  Crossing into Texas, the landscape opened up in a big way—wide plains, endless skies, and a sense of space that felt freeing. I stopped at the U-Drop Inn in Shamrock, sprayed a little paint at Cadillac Ranch in Amarillo, and grabbed a bite at the Midpoint Café in Adrian, standing right at the halfway point between Chicago and Santa Monica. Cooler fall evenings made wandering these spots relaxed and unhurried.

Me at Cadillac Ranch

Cadillac Ranch: Something everyone should see

The Big Texan—all I can say is this is a must-stop!

Driving conditions & atmosphere

The driving itself was easy and enjoyable. Highs stayed mostly in the 60s and 70s in the Midwest and into the 70s and 80s in Texas, with cool mornings and evenings. The roads were smooth and simple to follow, and the lack of crowds made everything—from diners to roadside attractions—feel more personal. The overall vibe was calm, nostalgic, and reflective, perfectly matched to the season.

I drove my (brand-new at the time) 2010 Camaro and loved every second

Recommended trip length

For this segment, six to eight days felt just right—enough time to really experience the highlights without feeling like I was checking boxes.

Overall experience

Driving Route 66 from Chicago to Texas in October gave me the Mother Road at its best. Historic gems, classic Americana, friendly small towns, and unforgettable landscapes came together under fall skies, turning the journey into something more than a road trip—it became a collection of moments I still think about long after the miles ended.

One of the best trips. I met so many wonderful people!

• Route 66 isn’t one single road
  Much of the original route follows old alignments that run alongside I-55, I-44, and I-40. Without a Route 66–specific map or app, it’s easy to miss some of the most iconic stretches.

• Historic motels book fast
  Places like the Wagon Wheel Motel (Cuba, MO) and Boots Court (Carthage, MO) fill up quickly in October. These stays are part of the experience, so it’s worth reserving early.

• This isn’t a “get there fast” drive
  Plan for short driving days and lots of stops. Route 66 rewards slowing down—the real magic happens in the small towns between the major stops.

• Support local along the way
  Family-run diners, small museums, gift shops, and motels depend on Route 66 travelers. Even a quick meal or souvenir helps keep the Mother Road alive.

• October weather can shift quickly
  Expect cool mornings, warm afternoons, and breezy evenings. Layers are key, especially in Illinois and Missouri—keep a light jacket within reach.

• Roadside photo ops come fast
  Attractions like the Blue Whale of Catoosa, Cadillac Ranch, the Gemini Giant, and colorful town murals often appear with little warning. Keep your camera ready.

• Carry some cash
  A few classic diners, small museums, and quirky attractions are still cash-only. Having $20 to $40 in small bills is a smart move.

• Eat at least one local specialty per state. The food is part of the Route 66 story.

  • Illinois: Cozy Dog in Springfield

  • Missouri: Kansas City–style BBQ

  • Oklahoma: Onion burgers around El Reno or Tulsa

  • Texas: Panhandle steakhouse classics

• Don’t skip the Route 66 Museums
  Each one tells a different chapter of the road’s history. Highlights include Pontiac (IL), Lebanon (MO), Clinton (OK), and Elk City (OK).

• Take the side roads
  Some of the best memories come from short detours—town squares, local parks, murals, antique shops, and roadside markets. Give yourself permission to wander.

• Bring a Sharpie or spray paint for Cadillac Ranch
  Leaving your mark is a Texas Route 66 tradition. Just be respectful and leave no trash behind.

• Talk to the locals
  Many business owners are storytellers who’ve lived Route 66 history firsthand. Ask questions—you’ll hear stories you won’t find on any map.

• Don’t rush the Texas stretch
  The drive between Shamrock and Amarillo is often underestimated. Neon signs, Art Deco architecture, and vast open skies make it one of the most memorable parts of the journey.

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