Route 66 Illinois Travel Itinerary: Road Trip from Chicago to St. Louis
Route 66 Shield Mural in Pontiac Illinois
Darley taking in the mural art in the alley behind the Route 66 Hall of Fame Museum in Pontiac
Follow Darley Newman’s Route 66 Illinois Road Trip Itinerary from Chicago to St. Louis, stopping for Cozy Dogs, classic milkshakes, antiquing, historic haunts and diners. Few American road trips capture the imagination quite like Route 66. In Illinois, the legendary “Mother Road” begins in downtown Chicago and winds southwest toward St. Louis, connecting travelers with vintage diners, quirky roadside attractions, historic service stations, classic neon, and stories that bring the past vividly to life.
The Route 66 Road Itinerary
On this Illinois Route 66 journey for Travels with Darley, Darley traveled from Chicago to St. Louis, discovering family-run businesses, restored landmarks, and communities dedicated to preserving this iconic stretch of road. Here’s a look at the itinerary—and plenty of inspiration for planning your own Route 66 Illinois adventure.
Day 1 – Chicago to Joliet
Start your Route 66 journey in downtown Chicago
There’s no better place to begin than at the Historic Route 66 Begin Sign on East Adams Street near Michigan Avenue, right by the Art Institute of Chicago. This is the symbolic eastern starting point of Route 66, and it’s a must for that first photo before heading out on the open road.
From there, take time to enjoy downtown Chicago on foot. A walk through Grant Park leads to Buckingham Fountain, one of the largest fountains in the world. Opened in 1927, just a year after Route 66 was established, the fountain is a classic Chicago landmark and a beautiful way to ease into the journey.
Leaving the city, a fun first stop for families is the Route 66 Playground at Harvester Park in Burr Ridge. This colorful, themed playground celebrates roadside attractions and landmarks from all eight Route 66 states, turning a roadside break into a playful learning experience.
For dinner, head to White Fence Farm in Romeoville, a longtime local favorite known for fried chicken, Brandy ice cream, and a nostalgic atmosphere. The restaurant also features antique cars and even alpacas and mini goats, making it a memorable stop before overnighting in Joliet.
Day 2 – Joliet, Wilmington, Braidwood, Dwight, and Pontiac
Historic prison walls, giant roadside icons, and classic Route 66 vibes
Begin the day in Joliet at the haunting and fascinating Old Joliet Prison. Opened in 1858 and closed in 2002, the prison offers a striking look at Illinois history and has appeared in pop culture favorites including The Blues Brothers and Prison Break. Its massive limestone walls and preserved spaces make it one of the most unusual stops on Route 66.
From Joliet, continue to Wilmington to see the famous Gemini Giant, one of Route 66’s beloved Muffler Man statues. Standing tall outside the historic Launching Pad, this oversized spaceman is one of the most recognizable roadside attractions on the route.
Lunch is a retro treat at the Polk-a-Dot Drive In in Braidwood, where burgers, shakes, and life-sized statues of pop culture icons like Elvis, Marilyn Monroe, Betty Boop, and the Blues Brothers create a photo-worthy stop full of nostalgia.
Next, head to Ambler’s Texaco Gas Station in Dwight, a beautifully restored 1940s-era station that now serves as a Route 66 welcome center. Listed on the National Register of Historic Places, it’s one of those stops that instantly transports you to another era of American road travel.
For a modern contrast, stop in Pontiac at Wally’s, a supersized gas station and travel center with EV chargers, road trip snacks, barbecue, and just about everything else a traveler could want. Route 66 may celebrate the past, but it’s also evolving with the future.
Spend the night in Pontiac or continue on depending on your pace.
Old Joliet Prison
Darley channeling the 50s along Route 66 as she busts out of Old Joliet Prison in a 1967 Oldsmobile Cutlass 442. The Prison has made several appearances in films in television including the 1980 film, “The Blues Brothers” and the critically acclaimed Fox series “Prison Break.”
Day 3 - Pontiac, Normal, and Springfield
Pontiac is one of the most vibrant Route 66 towns in Illinois. Start with the giant Route 66 shield mural at the Route 66 Hall of Fame and Museum, one of the most iconic photo ops on the road. Pontiac is also home to more than 20 murals, making it a great stop for anyone who loves public art and small-town Americana.
Continue south to Normal to visit Sprague’s Super Service Station, also known today as Ryburn Place. This restored Tudor Revival gas station from 1931 is one of the most architecturally distinctive stations on Route 66 and tells the story of how independent business owners once created memorable stops for motorists.
Then it’s on to Springfield, one of the richest destinations on Illinois Route 66 for both history and food.
Start with a meal at the legendary Cozy Dog Drive In, home of the original “Cozy Dog,” Springfield’s famous hot dog on a stick. This family-run institution has been serving travelers since the 1940s and remains one of the most beloved Route 66 dining stops anywhere.
After lunch, explore the Lincoln Home National Historic Site, where Abraham Lincoln lived before becoming president. This beautifully preserved neighborhood adds a deeper historical layer to any Route 66 trip, connecting the road journey with the story of Lincoln and Springfield’s diverse 19th-century community.
Later, visit the Route 66 Experience at Gate 2 of the Illinois State Fairgrounds, an educational outdoor exhibit featuring neon signs, vintage billboards, and tributes to communities across Illinois Route 66.
End the evening at Motorheads in Springfield, a lively restaurant, museum, and gathering place packed with car culture, Route 66 memorabilia, and local flavor. It’s also a great place to try a horseshoe, Springfield’s famous open-faced sandwich piled with fries and cheese sauce.
Spend the night in Springfield.
Abraham Lincoln’s home in Springfield, IL
Darley Newman and National Park Ranger Jasmine Leung in front of the Lincoln Home in Springfield, IL. This is the first and only home Abraham Lincoln owned. It is a place of stories and memories of Abraham Lincoln and his family as well as Lincoln's growth from a young lawyer of humble origin to the highest position in the United States.
Day 4 - Springfield to Collinsville
Brick roads, soda fountains, historic cafés, and giant roadside whimsy
South of Springfield, begin the day with a drive along the Auburn Brick Road, a restored 1.4-mile stretch of hand-laid brick pavement dating to 1931. This is one of the most atmospheric places to experience what early Route 66 travel may have felt like.
In Girard, stop at Docs Just Off 66, a historic soda fountain and former drugstore dating back to the 19th century. Restored and revived, it’s a delightful place to soak up nostalgia and enjoy the old-fashioned setting.
Next, make your way to Litchfield for lunch at the Ariston Café, one of the oldest continuously operating restaurants on all of Route 66. Established in 1924 and relocated to Route 66 in 1935, the Ariston is a true classic, serving travelers for generations.
Continue to Livingston to explore the Pink Elephant Antique Mall, a delightfully eccentric Route 66 stop filled with antiques, collectibles, candy, diner fun, and giant fiberglass figures. It’s the kind of roadside attraction that makes Route 66 so memorable.
In nearby Edwardsville, the restored West End Service Station offers another glimpse into the golden age of road travel. Once a bustling station for motorists on Route 66, it now stands as an interpretive historic site and visitor center.
A short drive away in Collinsville, don’t miss the World’s Largest Catsup Bottle, a 170-foot-tall water tower built in 1949. It’s one of Illinois’ most famous roadside oddities and a beloved example of oversized Americana.
For dinner, head to Old Herald Brewery & Distillery in Collinsville, a family-friendly stop in a historic newspaper building. Craft beverages, local history, and a welcoming atmosphere make this a great final night stop before reaching the Mississippi River region.
Spend the night in Collinsville.
Docs Just Off 66
Darley with female entrepreneur, Casey Claypool of Docs Just Off 66 in Girard, IL. Docs Just Off 66 has successfully preserved the history of the 1884 original Decks drugstore and nostalgia of this historic business in Girard, Illinois. The nostalgic soda fountain is still in place, and all the relics from the pharmacy museum remain on display.
Day 5 - Cahokia Mounds and the Chain of Rocks Bridge
Ancient history and a dramatic ending to the Illinois Route 66 journey
Before wrapping up the trip, make time for Cahokia Mounds State Historic Site, a UNESCO World Heritage Site and one of the most important archaeological sites in North America. Once the center of the largest pre-Columbian settlement north of Mexico, Cahokia adds a profound historical dimension to this journey.
Climbing Monks Mound rewards visitors with wide views of the landscape and even glimpses toward St. Louis. It’s a powerful reminder that this region’s story extends far beyond Route 66.
For a fitting final stop, head to the Chain of Rocks Bridge. This mile-long bridge over the Mississippi River, famous for its unusual 30-degree bend, carried Route 66 traffic from 1936 to 1967. Today it’s open to pedestrians and cyclists and offers a memorable final walk before crossing into the St. Louis area.
It’s the perfect ending to an Illinois Route 66 road trip: scenic, historic, and full of character.
Why Drive Route 66 in Illinois?
Illinois packs an incredible range of experiences into its stretch of Route 66. You’ll find:
Big-city landmarks in Chicago
Family-friendly roadside attractions
Historic diners and soda fountains
Restored service stations and motels
Deep ties to Abraham Lincoln and Illinois history
Vibrant local communities keeping the Mother Road alive
What makes this road trip so special is not just the landmarks, but the people—owners, preservationists, historians, and locals who continue to care for Route 66 and share it with travelers today.
Plan Your Own Illinois Route 66 Road Trip
Driving Route 66 through Illinois is about more than nostalgia. It’s about slowing down, pulling over often, meeting people, and discovering the stories behind the signs, diners, bridges, and backroads.
From Chicago to St. Louis, this Illinois itinerary is filled with unforgettable stops that blend Americana, history, food, and fun. Whether you’re traveling in a vintage car, on a motorcycle, or in a modern road trip vehicle, Route 66 in Illinois still delivers that timeless sense of adventure.
