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Route 66 Trip Guide: Chicago to Dallas
Experience the ultimate motorcycle journey along America's most iconic highway. Join us June 2nd to 8th, 2025 for an unforgettable adventure from the Windy City to the heart of Texas.
Chicago to Bloomington: Photo Opportunities
Start your journey with iconic photo opportunities in the Chicago to Bloomington stretch. Capture the "Beginning Route 66" sign in Chicago, the reflective Cloud Gate ("The Bean") in Millennium Park, and the towering Gemini Giant spaceman statue at the Launching Pad restaurant.
Don't miss the 50's vibe at Polk-A-Dot Drive-In, the historic Sprague Super Service Station, and the rustic charm of Funks Grove Sirup. For true Route 66 enthusiasts, walk on a section of the original concrete road in Towanda and explore the comprehensive Pontiac 66 Museum.
Budget Lodging Along the Route
Route 66 Motels
Experience the nostalgia and affordability of historic motels along the Mother Road, offering authentic Route 66 charm at budget-friendly prices.
Chain Hotels
Look for budget chains like Motel 6, Super 8, or Econo Lodge in cities like Bloomington, Springfield, and Oklahoma City for reliable accommodations.
Local B&Bs
Often providing more character for similar prices to budget motels, local bed and breakfasts offer a homey atmosphere and local insights.
Camping
If you're equipped for it, camping can significantly reduce accommodation costs, with sites available near major stops for $30-45 per night.
Texas Photo Opportunities
VW Slug Bug Ranch
This quirky roadside attraction features partially buried Volkswagen Beetles, similar to the famous Cadillac Ranch. It's a perfect spot for unique photos and won't cost you anything to visit.
Groom Cross
This impressive 19-story cross is visible for miles as you drive along Route 66. The base features statues depicting the life of Jesus, making it both a spiritual and photographic landmark.
U Drop Inn Cafe
Built in 1936 and known as the Tower Station, this iconic Route 66 building was recreated in the Pixar movie "Cars." While it no longer serves food, it functions as a museum and shop perfect for photography.
Oklahoma's Route 66 Treasures
Sand Hill Curiosity Shop
In Erick, Oklahoma, find this fascinating shop home to Harley, who was the inspiration for Mater in the "Cars" movie. The shop is filled with memorabilia and makes for fantastic photos both inside and out.
National Route 66 Museum
Located in Elk City, this museum offers interactive exhibits including cars you can sit in. Outside, you'll find one of the largest Route 66 signs in the world, making it a perfect photo opportunity.
Pop's Soda Shop
For an unforgettable nighttime photo, visit Pop's Soda Shop where a four-story tall LED soda bottle changes colors continuously. This spectacular display is worth the 30-minute drive from Oklahoma City.
Getting Your Motorcycle to Chicago
Option 1: Fly and Rent
Pros: No need to own a motorcycle, newest models with full warranty and roadside assistance, no long-term maintenance concerns.
Cons: Most expensive option, limited selection of models, less personalized experience.
Option 2: Ship Your Bike, Fly Yourself
Pros: Ride your own motorcycle, more comfortable with your own setup, no rental limitations or restrictions.
Cons: Coordinating shipping logistics, need to arrange shipping at both ends, time constraints with shipping schedules.
Option 3: Ship Both Ways + Fly
Pros: Less overall riding time, experience only the best parts of Route 66, no need to ride back if time is limited.
Cons: Less authentic Route 66 experience, highest shipping costs, most logistical coordination required.
Day-by-Day Itinerary
Day 1: Chicago to Springfield, IL (200 miles)
Pick up motorcycle in Chicago, visit Route 66 Begin Sign, The Bean at Millennium Park, Gemini Giant spaceman statue, and Polk-A-Dot Drive-In. Stay in budget motels in Springfield ($70-90/night) or camping at Springfield/Route 66 KOA ($35-45/night).
Day 2: Springfield to Carthage, MO (380 miles)
Visit Chain of Rocks Bridge, Ted Drewes Frozen Custard, Route 66 State Park, and Route 66 Ridley Motorcycles in Carthage. Stay in budget motels in Carthage ($60-80/night) or camping at nearby sites ($30-40/night).
Day 3: Carthage to Oklahoma City (210 miles)
Visit Seaba Station Motorcycle Museum, Ed Galloway's Totem Pole Park, Blue Whale of Catoosa, and Pop's Soda Shop. Stay in budget motels in OKC ($75-95/night) or camping at nearby sites ($35-45/night).
Day 4: Oklahoma City to Amarillo (260 miles)
Visit Route 66 Vintage Iron Motorcycle Museum in Miami, OK and U-Drop Inn Café. Continue your journey toward Dallas with unforgettable memories of America's historic highway.
Motorcycle Museums Along Route 66

Route 66 Ridley Motorcycles
Located in Carthage, this stop offers a glimpse into American motorcycle manufacturing history with vintage models and memorabilia.

Seaba Station Motorcycle Museum
In Warwick, OK, this converted 1921 gas station houses an impressive collection of vintage motorcycles from various eras and manufacturers.

Route 66 Vintage Iron
This Miami, OK museum showcases classic motorcycles with a focus on American brands and their role in Route 66 history.

Photography Opportunities
Each museum offers unique backdrops for motorcycle enthusiasts to capture memorable photos of historic bikes against Route 66 settings.
Texas Photo Opportunities
Cadillac Ranch
Ten graffiti-covered Cadillacs buried nose-down near Amarillo. Bring spray paint to leave your mark on this iconic installation.
Big Texan Steak Ranch
Capture the famous 72-oz steak challenge sign. The giant cowboy statue makes for perfect Route 66 memorabilia shots.
Midpoint Café
Snap a photo at the exact midpoint between Chicago and LA. The vintage diner serves famous "Ugly Crust Pies" worth documenting.
VW Slug Bug Ranch
Lesser-known cousin to Cadillac Ranch. Five Volkswagen Beetles buried hood-first in Conway create a quirky photo backdrop.
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