Lake Michigan, the Gateway Arch, Abraham Lincoln’s former home, original portions of iconic Route 66… they’re among the many highlights on a Chicago to St. Louis road trip!
The drive between St. Louis, Missouri and Chicago, Illinois is one of the great adventures of the Midwest. As a decade-long Chicago resident, I drove this route numerous times.
Most people just take the highway straight there, which results in a tidy 4-hour drive without many highlights.
But I always suggest that folks take the longer route that includes part of old Illinois Route 66 and passes through tons of quirky small towns.
There’s a third possible route that includes Casey, Illinois, a small town that has become famous for its giant roadside attractions, and Olney, Illinois, known for its large albino squirrel population!
Let’s review the best routes available for anyone looking to make turn the Chicago to St. Louis road trip into a scenic drive with lots of fun stops along the way.
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Chicago to St. Louis Road Trip: Three Possible Routes
So, let’s go over the options. The first route involves simply heading straight down I-55. That’s a boring route, because it’s entirely highway. But it’s the fastest route.
A cooler option is to travel by old Route 66, which runs somewhat parallel to I-55 as it weaves its way through small towns in Illinois.
A third, less-explored option is to detour through the town of Casey, which is known for its collection of “world’s largest” roadside attractions, including the world’s largest rocking chair, mailbox, golf driver, and many more!
My personal suggestion for avid road trippers is to drive from Chicago to St. Louis via old Route 66, and return from St. Louis to Chicago via the more eastern route that goes through Casey.
Here’s the scoop on each of these possible driving routes between the Windy City and the Gateway to the West.
Road Trip Option #1: Take I-55 All the Way
Drive Time: 4 hours, 20 minutes
Recommended stops: Bloomington, Springfield
Total time including stops: 6-7 hours
The distance from Chicago to St. Louis is just under 300 miles if you stay on I-55 all the way. This highway route does pass by two cities worth stopping at – Bloomington and Springfield.
Bloomington and the adjacent town of Normal, Illinois have roughly 200,000 residents in the combined region. Located two hours from Chicago, it’s a good place for a mid-morning break or lunch stop.
Bloomington is home to the Route 66 Visitor Center (officially called Cruisin’ with Lincoln on 66 Visitors Center and Gift Shop). Admission is free from 9 am to 5 pm everyday except Sunday (open til 9 pm on Tuesday.)
As the capital of Illinois, meanwhile, Springfield has loads of history, much of it related to President Lincoln. Allow a couple hours to see the Abraham Lincoln Presidential Library and the Lincoln Home National Historic Site.
Still, sticking to the highway doesn’t count as a real road trip. So I strongly advise taking road trip option #2 and traveling on Route 66 instead!
Road Trip Option #2: Historic Route 66
Drive Time: 5 hours, 55 minutes
Recommended stops: Joliet, Wilmington, Gardner, Pontiac, Bloomington, Atlanta, Lincoln, Springfield, Auburn, Nilwood, Litchfield, Madison
Total time including stops: 9-13 hours
Historic Route 66 actually starts right in downtown Chicago, running all the way to Santa Monica, California.
Much of the original Route 66 is now gone, having been paved over or removed. But Illinois has several stretches where you can still see the old route.
Taking this route adds a lot of extra time to the Chicago to St. Louis road trip – but it also makes the drive much more exciting!
The speed limit in many of these small towns is as low as 25, so prepare to take your time.
Start by visiting the Route 66 sign in downtown Chicago that marks the start of the journey. It’s not far from Lake Michigan.
Then proceed to Joliet, home of the Route 66 Welcome Center (it will be closed if you start your journey early in the morning.)
Joliet is also the home of Dick’s on 66, a service station with bricks from the old Route 66, and Rich & Creamy, a classic ice cream stand with Blues Brothers statues on the roof.
Head to Wilmington’s Launching Pad restaurant, which has the “Gemini Giant” Muffler Man statue.
Stop at the Polka Dot Drive-In in Braidwood, which has statues of Americana favorites like Elvis and Marilyn Monroe.
Gardner has an old streetcar which used to be a diner. That sits next to a historic tiny jail that visitors can go inside and explore.
The towns of Dwight and Odell both have vintage gas stations with old-fashioned pumps. The pumps aren’t functional anymore, but seeing them creates a sense of nostalgia that feels like old Route 66.
The town of Pontiac is a must-visit, due to the 23 impressive murals around the city. There’s also an Abraham Lincoln statue near the courthouse.
Pontiac is the home of the Route 66 Hall of Fame and Museum. It’s an old-fashioned museum filled with memorabilia and photos of just about every spot along Illinois Route 66.
Chenoa has a parklet at US Highway 24 & Old Route 66 where pavement from the old highway still exists. You can walk on old Route 66 and imagine how things would have looked here 100 years ago!
Towanda also has an old section of Route 66 called Dead Man’s Curve, although, by today’s standards, it’s not much of a curve at all. It’s hard to believe anyone could’ve been going fast enough to have an accident around this gentle curve.
Bloomington has the free Cruisin’ with Lincoln on 66 Visitors Center.
The town of Atlanta, Illinois has a couple quirky attractions close together. There’s Atlanta Route 66 Park, a small parklet with signage about Route 66.
And there’s the “Bunyon Giant” Muffler Man – a Paul Bunyan character holding a giant hot dog.
Lincoln, Illinois has the Mill Museum (currently closed for renovation), and the Railsplitter, aka the world’s largest covered wagon. It’s 25 feet tall and 40 feet long, and features an Abe Lincoln statue at the front.
Interestingly, the covered wagon was missing its cover when I visited.
Elkhart has a Route 66 mural, and Williamsville has a gas station called Old Station.
Leave some time to explore Springfield. I enjoyed the Lincoln Presidential Library, which has video displays and exhibits about the 16th president’s life and administration.
Springfield also has a couple fun roadside attractions, including the Muffler Man statue at Lauterbach Tire and the Pink Elephant with a martini sitting in a strip mall parking lot.
The towns of Virden and Carlinville both have Route 66 murals, while the towns of Auburn and Nilwood both have old sections of Route 66.
The Auburn section is 1.4 miles of brick road. Though this road was part of Route 66 from 1926 to 1930, the bricks weren’t laid until 1931. So technically, the bricks were not part of Route 66. But it’s still an interesting drive.
Meanwhile, in Nilwood is a weird part of Route 66 where a turkey from a local farm stepped in the concrete back in the 1920s just as it was drying. The turkey footprints became embedded in the road, where they remain today, a full century later. Look for the wooden turkey sign next to the road.
Litchfield has a Route 66 Welcome Center and a large mural, and Livingston has the Pink Elephant Antique Mall.
Finally, just before reaching St. Louis, stop at the Old Chain of Rocks Bridge in Madison, Illinois. The bridge spans the Mississippi River. It was constructed in 1929, and in 1936 Route 66 was rerouted over the bridge.
Thousands of vehicles crossed this bridge while making the cross-country drive. Today, the bridge is only open for pedestrians. You can park and then walk across the Mississippi on this important monument of American road trip history.
This drive took me about 13 hours, because I made every stop. I left Chicago at 7 am and arrived to St. Louis around 8 pm. You could make the road trip shorter by removing some of the non-essential stops.
See below for a detailed map and full list of places to stop on your Illinois Route 66 adventure!
Full List of Stops on an Illinois Route 66 Road Trip
Here’s the complete list of places worth stopping on Illinois Route 66, and a Google map so you can make sure to hit them all!
Chicago: Route 66 sign (E. Adams St & S. Michigan Ave.)
Joliet: Route 66 Welcome Center, Rich & Creamy Ice Cream, Dick’s on 66
Wilmington: Launching Pad restaurant / Gemini Giant statue
Braidwood: Polka Dot Drive In
Godley: Route 66 Mining Museum
Gardner: Streetcar Diner, Gardner Jail
Dwight: Ambler’s Texaco
Odell: Standard Oil Gas Station
Pontiac: Route 66 Hall of Fame & Museum, 23 murals, Lincoln statue
Chenoa: Remnants of old Route 66
Towanda: Dead Man’s Curve
Normal: Sprague’s Super Service
Bloomington: Cruisin’ With Lincoln on 66 Visitors Center
Atlanta: Atlanta Route 66 Park, Bunyon Giant Hot Dog Muffler Man
Lincoln: Railsplitter (the World’s Largest Covered Wagon), the Mill Museum
Elkhart: Route 66 Mural
Williamsville: Old Station Gas Station
Springfield: State Capitol building, Abraham Lincoln Presidential Library, Lincoln Home National Historic Site, Pink Elephant with Martini, Lauterbach Tire Muffler Man
Auburn: 1.4-mile section of brick road Route 66 from 1932
Virden: Route 66 mural
Nilwood: Turkey tracks on Donaldson Road
Carlinville: Route 66 mural
Litchfield: Litchfield Museum & Route 66 Welcome Center
Mt. Olive: Soulsby Shell Gas Station
Livingston: Pink Elephant Antique Mall & Twistee Treat Diner
Madison: Old Chain of Rocks Bridge
Road Trip Option #3: Visit Olney and Casey to See the White Squirrels and Giant Attractions
Drive Time: 6 hours, 45 minutes
Recommended stops: Champaign, Casey, Olney, Collinsville
Total time including stops: 10-13 hours
The quirky third option for driving between St. Louis and Chicago involves a path through eastern Illinois. The big city on this route is Champaign, but the real highlights are Casey and Olney.
Champaign is just over 2 hours from Chicago and will be the first stop on this journey. Explore the University of Illinois campus, walk the Boneyard Creek Trail, visit the Krannert Art Museum, or just find a modern restaurant for lunch.
Ninety minutes later, you’ll reach Casey, Illinois, whose slogan is “big things in a small town.” Casey has a dozen Guinness World Record-holding attractions, including the world’s largest rocking chair…
And the world’s largest mailbox…
And the world’s largest golf driver, sitting right next to a giant mousetrap…
And the world’s largest pitchfork…
And the world’s largest barbershop pole (seen in the background with this enormous No. 2 pencil)…
And the world’s largest wooden shoes, inside the Wildflour Bakery (which makes a stellar banana cream cheesecake)…
There’s also the world’s largest truck key, the world’s largest teeter totter, the world’s largest wind chime, the world’s largest golf tee, the world’s largest swizzle spoon, and more. I saw them on during a single afternoon visit!
Casey has a bunch of other giant stuff that isn’t quite big enough to claim a world record, but is still impressive. Like a minion outside a coffee shop.
And this giant taco outside Cilantro’s Restaurant (they make a great salsa, btw):
And this big ruler:
And the giant bookworm at the library:
And the giant pizza slicer, with giant antlers across the street:
See a map of all the giant things in Casey here. They also have a giant crochet needle, a giant wooden token, giant piggy bank, and more. This is a kooky town and you will want to spend an hour or two walking around to see everything.
After Casey, it’s another hour to Olney, the small town known for its population of adorable white squirrels. The best time to spot one is early in the morning, but they can also be found at other times.
Head to City Park, and be patient. If the odds are in your favor, you may catch a glimpse of one of the 100-ish white squirrels in town.
I only saw one white squirrel myself, but it was so cool to watch!
Finally, before reaching St. Louis, stop by Collinsville, home of the world’s largest ketchup bottle. It’s one last giant attraction to add to your road trip itinerary.
FAQs for a Chicago to St. Louis Drive
What time of year is best to drive from Chicago to St. Louis?
Obviously, summer weather is best, but autumn is also warm and sunny. Any time between April and November is fine for this trip. You can go during winter or spring, but be prepared for possible rain or snow.
How many days do I need for this road trip?
As noted, you can make this journey in one day. But I suggest taking at least two days to complete the one-way drive.
That way, you can take your time and explore all the museums, small towns, and random shops. For a round-trip drive, consider 3-4 days in total.
Are there tourist information boards along the way?
Yes, lots! Many of the small towns on Route 66 have kiosk displays and tourist information boards. It’s easy to read and learn about how Route 66 affected each town along the route.
How much will gas cost for this road trip?
I usually suggest checking Gas Buddy since they have calculators you can tweak using your own car model and make.
Driving a compact rental car, I only needed about $70 worth of gas to complete a round-trip from Chicago to St. Louis and back.
What should I do in Chicago?
Hopefully you’re spending several days in the Windy City before heading out on this road trip, because there’s so much to do there!
Try the famous Architecture Boat Tour, stop by the Bean sculpture, explore the Garfield Park Conservatory, or visit the iconic Green Mill jazz club. See also our lists of Chicago winter activities and Chicago evening activities.
What should I do in St. Louis?
Ride the tram to the top of the arch for sweet views of the surrounding area. Then check out City Museum, a huge facility that is essentially like a playground for adults (though kids are welcome too.)
Also stop by Citygarden, a public park near the Arch that has lots of sculptures and outdoor art. Visit the Delmar Loop for one of the city’s trendiest neighborhoods, and finish off the trip with a brewski at the Budweiser Brewery Tour.
Are there any other possible detours on this road trip?
Sure, Illinois has plenty of other small towns you may want to explore, including Decatur and Peoria. If you really want to extend your journey, I’d suggest staying a few days in Springfield, since there’s so much history to see there.
What can I see if I keep driving past St. Louis?
Obviously, Route 66 keeps going all the way to California. If a cross-country journey isn’t in your schedule, you could leave Route 66 and proceed west across Missouri to Kansas City.
Do you have any suggestions for additional stops on a Chicago to St. Louis road trip via Route 66?