Harley Davidson and Route 66 – Is There a Better Match?
It had always been a dream of mine to ride a Harley Davidson down a stretch of the legendary Route 66. I had already driven some parts of the route by car, but this was my chance to experience it the right way—on the rumbling back of a Harley that shakes like a jackhammer. And yet, that unmistakable engine growl is music to the ears.
This journey was organized through the online motorcycle rental platform Twisted Road. The site works similarly to vacation rental services—bike owners list their motorcycles, which are available to rent at various locations throughout the U.S. They claim to be cheaper than large rental companies, but it’s important to check the condition of the bike when picking it up. Rentals range from $60 to $150 per day, depending on the location, type of motorcycle, and time of year. We started in Chicago and finished in St. Louis. Popular pick-up cities include Chicago, Miami, Los Angeles, and Austin.
Day 1: Chicago – The Start of a Legend
Start your ride at the official beginning of Route 66—Adams Street and Michigan Avenue in downtown Chicago. Here, you’ll find the iconic “Route 66 Begin” sign, a must-snap photo spot for travelers from around the globe.
Spend the day exploring Chicago—walk through Millennium Park, snap a selfie in front of “The Bean” (Cloud Gate), browse the shops along the Magnificent Mile, and enjoy the lakefront at Navy Pier. Architecture buffs should hop on the Chicago Architecture River Cruise for a unique view of the skyline.
Stay at a centrally located hotel for easy walking access to the attractions and secure parking for your bike. Chicago is worth at least three days, but we’ll save that for another article.
Day 2: Chicago – Joliet – Wilmington – Pontiac
Ride southwest through Chicago’s suburbs toward Joliet, home of the Old Joliet Prison—made famous in “The Blues Brothers.” Nearby, you’ll find the Route 66 Welcome Center and museum, filled with souvenirs and history.
Next stop: Wilmington, home of the fiberglass Gemini Giant standing guard outside the retro Launching Pad diner. We grabbed a classic hot dog and chips at Nelly’s, an old-school local joint.
Continue cruising through rural America to Pontiac, one of Illinois’ most charming Route 66 towns. Snap photos at roadside stops like the colorful Polk-a-Dot school bus and the vintage Amber Texaco Station.
In Pontiac, visit the Route 66 Hall of Fame and Museum—home to Bob Waldmire’s original VW bus. The town is also known for its more than 20 murals depicting Route 66 history.
Dinner was at Bob & Ringo’s Grill, a classic American spot right in the heart of town.
Day 3: Pontiac – Bloomington – Atlanta – Springfield
Begin with a relaxed ride to Bloomington, where you can browse antique shops or grab a coffee in one of the vintage diners.
Your next stop is Atlanta, IL—home of the massive Bunyon Giant muffler man holding a hot dog. Across the street, you’ll find a mini museum and more roadside giants, once used as marketing gimmicks.
Although the Palms Grill Café in Atlanta is a charming lunch spot, we kept going and had lunch in Springfield at the Stadium Smokehouse Bar & Grill. The Bourbon Burger was a standout.
Across from the old venue where Johnny Cash once played, we explored the Route 66 Experience on the fairgrounds—featuring vintage neon signs. Don’t miss the Ace Sign Museum on South 1st Street for more open-air nostalgia.
Springfield is rich in history. Visit the Abraham Lincoln Presidential Library and Museum and the Lincoln Home Historic Site for insight into America’s 16th president.
We capped off the evening at Motorheads, a combination restaurant and museum with great pizza and a vibrant crowd.
Day 4: Springfield – Carlinville – Litchfield – Collinsville
Spend the morning exploring more of Springfield. We visited the quirky Pharmacy Gallery, which displays some of the earliest Route 66 maps.
In Carlinville, check out Cannonball Jail and the Million Dollar Courthouse—an unexpectedly extravagant piece of local history.
Stop for lunch at the historic Ariston Café in Litchfield, serving Route 66 travelers since 1924. Then, grab dessert at the Pink Elephant Antique Mall—a giant pink elephant marks the spot. Besides great ice cream, there’s a quirky antiques shop and a fun souvenir store. Don’t forget a photo with the flying saucer and little green men out front!
That evening, we arrived in Collinsville. After dinner at Jerry’s Cafeteria in Granite City, we enjoyed a live band at Neon Sign Park and ended the night with cocktails at Speakeasy, a retro bar with amazing ambiance and a Frank Sinatra-style crooner.
Day 5: Collinsville – Alton – Grafton
We visited the Worldwide Technology Raceway in Madison, where we took a few laps on the Nascar/Indy-style oval track. From the stands, you get an incredible view of St. Louis and the iconic Gateway Arch.
Riding along the Mississippi River, we reached the small town of Alton. After lunch at Bluff City Grill, we browsed souvenir and craft shops.
About 10 miles farther, we reached our final stop: Aerie’s Resort, perched above the river. The organizer had arranged a truck to transport our bikes back to Chicago, while we hopped into a van that also carried our luggage.
We ended the trip with a celebration at Grafton Winery, surrounded by vineyards, music, and fireworks. The next day, we all parted ways—my journey took me back to Chicago, then on to Vienna via LOT Polish Airlines through Warsaw.
Travel Tips:
Best time to ride: May–September
Navigation: Download the “Route 66 Navigation” mobile app
Total ride: ~500 km, comfortably spread over 5 days
Pacing: No ride was longer than 90 minutes, making it ideal for all skill levels
Pro tip: Strengthen your back and arms before the trip—after 30 minutes, those neck muscles feel it
Expect to See: Vintage gas stations, classic neon signs, colorful murals, and endless cornfields
Don’t Forget: Extra phone memory and a retro road trip playlist
Five days on Illinois’ Route 66 give you the perfect blend of Americana charm, historic sites, hearty food, and wide-open rural landscapes.
This short but rich segment is ideal for Route 66 first-timers—and will leave you wanting more. That said, I was personally content with just five days. Most of the road runs through endless cornfields and quiet backroads, far from the bright lights of major cities. It’s the real America—exactly what most Americans live every day. For me, five days were just enough to experience the thrill of Harley-powered freedom on the Mother Road.
How to Spend 3 Perfect Days in Chicago — America’s Best Big City
