Kicking Off Route 66 from Chicago to St. Louis

Start Where It All Began

If you’re a Route 66 purist or just someone who loves a good story, beginning your journey at the very start—in downtown Chicago—is a must. This bonus leg sets the tone for the adventure ahead. It winds through restored gas stations, giant roadside icons, cozy diners, and towns steeped in history.

Begin your morning beneath the skyscrapers of Chicago at the Route 66 “Begin” sign at Adams Street and Michigan Avenue. Just steps away, grab breakfast at Lou Mitchell’s, a Chicago institution since 1923. It’s a rite of passage for Route 66 travelers!

If time allows before you hit the road, you might wander through the Art Institute of Chicago, take in the city from the Skydeck at Willis Tower, or snap a selfie at “The Bean” in Millennium Park. But don’t hang out too long—there’s A LOT of road ahead.

This add-on day lets you experience the true beginning of Route 66—from its official start sign in downtown Chicago to the riverside city of St. Louis. While less rugged than the western stretches, this segment is rich in Americana. It is delightfully packed with restored diners, old gas stations, and roadside giants.

If you want to experience every mile of Route 66 the way it was originally intended—starting from its official birthplace in Chicago, Illinois—this optional pre-trip day is for you. My main itinerary begins in St. Louis. However, you can add this “Bonus Day” to trace the legendary Mother Road from its very first mile.

This extra leg winds through vintage diners, muffler men, Lincoln landmarks, and classic small-town Americana—perfect for a solo trip, a weekend adventure, or a chance to “complete the route” if you’re returning to the Midwest. It’s a great way to set the tone for what’s to come. Travelers always need even more nostalgia to pack into a cross-country drive.

On the Road: Old Route 66 through Illinois

Distance: ~300 miles
Drive Time: 5.5–6 hours (plus stops)
Theme: Americana nostalgia, small-town charm, and Abraham Lincoln history

As you leave the city behind, Route 66 begins to unfold its character. Signs and markers guide you through Chicago’s suburbs and into small-town Illinois. This is where the heart of the Mother Road truly comes alive.

Your first major stop is Joliet. Here, you can visit the Route 66 Welcome Center inside the Joliet Area Historical Museum. Just a few blocks away, the old Joliet Prison offers a great photo op and a little eerie history.

Heading south, Wilmington greets you with one of Route 66’s most iconic roadside giants: the Gemini Giant. He stands tall outside the Launching Pad Drive-In. It’s a must-stop for quirky photos.

In the stretch between Braidwood, Dwight, and Odell, you’ll find even more roadside charm. The Polk-a-Dot Drive-In is a colorful blast from the past, while Odell’s beautifully restored 1930s Standard Oil Station is a living postcard from another era.

Lunch and Murals in Pontiac

Pontiac is a natural place to pause for lunch and exploration. Home to the Route 66 Hall of Fame & Museum, this town is steeped in nostalgia. Across the street, the Livingston County War Museum tells stories of local veterans. Taking a short walk downtown reveals a collection of vibrant murals celebrating Route 66 and local history.

You can refuel at Old Log Cabin Diner, a classic American stop. You could also try Bernardi’s II if you’re in the mood for Italian comfort food.

Tall Statues and Big Wagons

Continue south to the town of Atlanta which offers more roadside Americana, including the towering Tall Paul Muffler Man and the retro Palms Grill Café. A little further along in Lincoln, don’t miss the World’s Largest Covered Wagon. It’s complete with a statue of Abraham Lincoln holding the reins. For those wanting more historical depth, the Lincoln Heritage Museum provides a meaningful stop.

History and Hot Dogs in Springfield

Springfield, the capital of Illinois, is where history and roadside kitsch converge. Here, you can visit the world-class Abraham Lincoln Presidential Library & Museum, take a walk past Lincoln’s beautifully preserved home, and maybe even spot the Old State Capitol building downtown.

Before hitting the road again, swing by the Cozy Dog Drive-In, where the corn dog-on-a-stick was invented. It’s pure Route 66 Americana – greasy, nostalgic, and delicious.

Arriving in St. Louis Along Route 66

As evening sets in, cross the Mississippi River and roll into St. Louis, Missouri – your gateway to the West. If you’re not in a rush, make a detour to Litchfield and dine at the historic Ariston Café, one of the oldest restaurants on Route 66. Or, if you’re craving something deeper, visit Cahokia Mounds – a UNESCO World Heritage site and one of the most significant Native American archaeological sites in North America. This stop will connect you to the sites you will experience on the western part of your Route 66 trek.

Once in St. Louis, stay near the Gateway Arch for stunning views and a chance to stroll across the Chain of Rocks Bridge. You’re now ready to begin the rest of your Route 66 adventure.

Overnight Options Along the Way

If you decide to split the drive into two days, both Pontiac and Springfield make excellent overnight stops—each offering a different kind of experience.

Pontiac is ideal if you’re drawn to a slower pace, vibrant murals, and classic small-town charm. The Three Roses Bed & Breakfast offers cozy, themed rooms filled with Route 66 nostalgia, while the Hampton Inn just off the interstate is a clean, reliable option for families or quick stays.

Springfield, on the other hand, is a haven for Lincoln history lovers and travelers wanting more dining and nightlife options. The Inn at 835 Boutique Hotel is a charming, historic property with a touch of luxury, while the President Abraham Lincoln DoubleTree by Hilton puts you in the heart of downtown, just steps from the city’s top historical attractions.

Final Thoughts

This bonus day is more than just a detour . . . it’s a celebration of where Route 66 truly begins. From the big city vibes of Chicago to the riverfront views of St. Louis, you’ll experience the road’s earliest memories and timeless magic. Whether you’re kicking off your full Route 66 drive or circling back to check off the beginning, this stretch adds character, color, and authenticity to your journey.

Ready to continue the ride? Head back to the 5-Day Route 66 Itinerary and let the Mother Road carry you west. Have you traveled this route? Post a comment on what your favorite stop was!

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