{"id":201607,"date":"2025-07-17T09:21:48","date_gmt":"2025-07-17T07:21:48","guid":{"rendered":"https:\/\/travel-advisor.eu\/?p=201607"},"modified":"2025-07-17T09:21:48","modified_gmt":"2025-07-17T07:21:48","slug":"harley-dreams-on-route-66-the-ultimate-illinois-road-trip","status":"publish","type":"post","link":"https:\/\/travel-advisor.eu\/en\/harley-dreams-on-route-66-the-ultimate-illinois-road-trip\/","title":{"rendered":"Harley Dreams on Route 66: The Ultimate Illinois Road Trip"},"content":{"rendered":"

Harley Davidson and Route 66 \u2013 Is There a Better Match?<\/h1>\n

\"Illinois<\/p>\n

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\u2014on the rumbling back of a Harley that shakes like a jackhammer. And yet, that unmistakable engine growl is music to the ears.<\/p>\n

This journey was organized through the online motorcycle rental platform Twisted Road. The site works similarly to vacation rental services\u2014bike 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\u2019s 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.<\/p>\n

Day 1: Chicago \u2013 The Start of a Legend<\/h3>\n

\"Illinois<\/p>\n

Start your ride at the official beginning of Route 66\u2014Adams Street and Michigan Avenue in downtown Chicago. Here, you\u2019ll find the iconic \u201cRoute 66 Begin\u201d sign, a must-snap photo spot for travelers from around the globe.<\/p>\n

Spend the day exploring Chicago\u2014walk through Millennium Park, snap a selfie in front of \u201cThe Bean\u201d (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.<\/p>\n

\"The<\/p>\n

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\u2019ll save that for another article.<\/p>\n

Day 2: Chicago \u2013 Joliet \u2013 Wilmington \u2013 Pontiac<\/h3>\n

\"Wilmington\"<\/p>\n

Ride southwest through Chicago\u2019s suburbs toward Joliet, home of the Old Joliet Prison\u2014made famous in “The Blues Brothers.” Nearby, you\u2019ll find the Route 66 Welcome Center and museum, filled with souvenirs and history.<\/p>\n

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\u2019s, an old-school local joint.<\/p>\n

Continue cruising through rural America to Pontiac, one of Illinois\u2019 most charming Route 66 towns. Snap photos at roadside stops like the colorful Polk-a-Dot school bus and the vintage Amber Texaco Station.<\/p>\n

\"Illinois<\/p>\n

In Pontiac, visit the Route 66 Hall of Fame and Museum\u2014home to Bob Waldmire\u2019s original VW bus. The town is also known for its more than 20 murals depicting Route 66 history.<\/p>\n

Dinner was at Bob & Ringo\u2019s Grill, a classic American spot right in the heart of town.<\/p>\n

Day 3: Pontiac \u2013 Bloomington \u2013 Atlanta \u2013 Springfield<\/h3>\n

\"Illinois<\/p>\n

Begin with a relaxed ride to Bloomington, where you can browse antique shops or grab a coffee in one of the vintage diners.<\/p>\n

Your next stop is Atlanta, IL\u2014home of the massive Bunyon Giant muffler man holding a hot dog. Across the street, you\u2019ll find a mini museum and more roadside giants, once used as marketing gimmicks.<\/p>\n

Although the Palms Grill Caf\u00e9 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.<\/p>\n

\"Illinois<\/p>\n

Across from the old venue where Johnny Cash once played, we explored the Route 66 Experience on the fairgrounds\u2014featuring vintage neon signs. Don\u2019t miss the Ace Sign Museum on South 1st Street for more open-air nostalgia.<\/p>\n

Springfield is rich in history. Visit the Abraham Lincoln Presidential Library and Museum and the Lincoln Home Historic Site for insight into America\u2019s 16th president.<\/p>\n

We capped off the evening at Motorheads, a combination restaurant and museum with great pizza and a vibrant crowd.<\/p>\n

Day 4: Springfield \u2013 Carlinville \u2013 Litchfield \u2013 Collinsville<\/h4>\n

\"Illinois<\/p>\n

Spend the morning exploring more of Springfield. We visited the quirky Pharmacy Gallery, which displays some of the earliest Route 66 maps.<\/p>\n

In Carlinville, check out Cannonball Jail and the Million Dollar Courthouse\u2014an unexpectedly extravagant piece of local history.<\/p>\n

\"Ameri\u010dki<\/p>\n

Stop for lunch at the historic Ariston Caf\u00e9 in Litchfield, serving Route 66 travelers since 1924. Then, grab dessert at the Pink Elephant Antique Mall\u2014a giant pink elephant marks the spot. Besides great ice cream, there\u2019s a quirky antiques shop and a fun souvenir store. Don\u2019t forget a photo with the flying saucer and little green men out front!<\/p>\n

\"Motorheads\"<\/p>\n

That evening, we arrived in Collinsville. After dinner at Jerry\u2019s 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.<\/p>\n

Day 5: Collinsville \u2013 Alton \u2013 Grafton<\/h3>\n

\"Illinois<\/p>\n

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.<\/p>\n

Riding along the Mississippi River, we reached the small town of Alton. After lunch at Bluff City Grill, we browsed souvenir and craft shops.<\/p>\n

About 10 miles farther, we reached our final stop: Aerie\u2019s 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.<\/p>\n

\"Mississippi\"<\/p>\n

We ended the trip with a celebration at Grafton Winery, surrounded by vineyards, music, and fireworks. The next day, we all parted ways\u2014my journey took me back to Chicago, then on to Vienna via LOT Polish Airlines through Warsaw.<\/p>\n

Travel Tips:<\/h3>\n

Best time to ride: May\u2013September<\/p>\n

Navigation: Download the \u201cRoute 66 Navigation\u201d mobile app<\/p>\n

Total ride: ~500 km, comfortably spread over 5 days<\/p>\n

Pacing: No ride was longer than 90 minutes, making it ideal for all skill levels<\/p>\n

Pro tip: Strengthen your back and arms before the trip\u2014after 30 minutes, those neck muscles feel it<\/p>\n

Expect to See: Vintage gas stations, classic neon signs, colorful murals, and endless cornfields<\/p>\n

Don\u2019t Forget: Extra phone memory and a retro road trip playlist<\/p>\n

\"Illinois<\/p>\n

Five days on Illinois\u2019 Route 66 give you the perfect blend of Americana charm, historic sites, hearty food, and wide-open rural landscapes.<\/h3>\n

This short but rich segment is ideal for Route 66 first-timers\u2014and 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\u2019s the real America\u2014exactly 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.<\/p>\n

How to Spend 3 Perfect Days in Chicago \u2014 America\u2019s Best Big City<\/a><\/p><\/blockquote>\n