Want to see what the United States is really like? Drive Route 66.
Route 66 epitomizes the freedom of the open road. The route became official in 1926, providing many small towns access to significant national roadways for the first time. Although it was decertified in 1985, the Mother Road lives on.
This scenic byway changed course over the years, and these alignments are well marked in Illinois. If you’re short on time, I-55 will take you from one attraction to the next, but the fun of driving one of the country’s most historic byways is in following its original path.
Keep your eyes peeled for wayside exhibits along Route 66 in Illinois. They tell some fascinating stories about the history of the route. There’s something to see at almost every turn, and before you know it you’ll be crossing the Mississippi.
There may be affiliate links in this post, which means we may get a small commission. It’s at no extra cost to you and helps keep TLT free. Everybody wins!
TLTip: Before you go, pick up a copy of Jerry McClanahan’s Easy Guide to Route 66.
Chicago to St. Louis Route 66 in Illinois Itinerary
Every Route 66 in Illinois adventure should begin at the beginning. Start your trip at the iconic Historic Illinois US 66 sign on Adams Street just west of Michigan Avenue. You can’t miss it: it’s covered in stickers.
A little further west, in the shadow of a tree and the L, is another sign, this one proclaiming “Illinois US 66 – Historic Route Begins.”
Before you start drive Route 66 from Chicago, take a moment to visit Buckingham Fountain. This iconic landmark was completed the year after Route 66 was established. Local art patron and philanthropist Kate Buckingham donated funds to Chicago for its construction in honor of her brother, Clarence.
You’ll want to make sure you’re fueled up for your big drive, so stop for a hearty breakfast at Lou Mitchell’s on Jackson Boulevard in Chicago’s Loop. Known for its big portions and fresh donut holes, this diner has been a staple since it opened in 1923, three years before Route 66 came to be.
Related: while you’re here, check out more things to do in Chicago
As you drive through Chicago toward the southwest suburbs, you’ll start to see brown Historic Route 66 signs. These are your friends, and they will guide you all the way to the Mississippi River.
You’ll have to pay close attention, though—Route 66’s alignment often changed, and navigating through all of those towns means it’s not a straight path. There’s usually only one sign per turn. Miss it, and you could end up backtracking.
(I speak from experience.)
Just outside of Chicago in Berwyn, notice the four wayside exhibits and the number of businesses with Route 66 in their names. This will give you a sense of the pride that Illinois takes in the Mother Road.
Berwyn is also home to the oldest White Castle on Route 66—it’s been serving sliders since 1939.
Another town with Route 66 pride is Joliet. Plan to spend some time there because, in addition to the Mother Road, Lincoln Highway cuts through the town and it’s also along the Illinois and Michigan Canal National Heritage Corridor.
Stop at Route 66 Park to browse the informational kiosks and admire the public art, including an old gas pump. Take a short stroll to an overlook of the Des Plaines River and the old Collins Street Prison, which you might recognize from The Blues Brothers.
Related: discover many more road trips from Chicago
Jake and Elwood themselves dance on the roof of Rich & Creamy, a seasonal ice cream shop that anchors the park.
Leave the park and cross the river to visit the Joliet Area Historical Museum and Route 66 Welcome Center, then swing by the Rialto Square Theatre. The oldest vaudevillian theatre on Route 66, it dates back to the same year as the certification of the Mother Road.
Stretch your legs, and maybe even glimpse some bison, at Midewin National Tallgrass Prairie.
This global treasure is the largest open space in the Chicago area, and was previously farmland, as well as the site of explosives manufacturing and storage. Now it’s a massive recreational area of thousands of acres with miles of trails. (And bison.
Did I mention bison?)
In Wilmington you’ll see one of the most photographed landmarks of Americana: the Gemini Giant. This fiberglass sculpture is one of four “Muffler Men” on Route 66 in Illinois—so named because several of the 1960s originals advertised muffler shops.
The Gemini Giant wears a space helmet and carries a rocket, and attracts visitors to The Launching Pad restaurant, which reopened after a two-year renovation in 2019. They’re open seasonally, so check before you go.
After your photo op with the giant, continue to Braidwood and the Polk-a-Dot Drive In. There you can snap some pics with Elvis and Superman, and those Blues Brothers make another appearance.
Before you resume your trip on Route 66 in Illinois, swing through the drive-through for a burger and chili cheese fries.
Dwight is another town that will grab your attention. Make your first stop Ambler’s Texaco Gas Station. The official Dwight Visitor Center, it’s completely run by volunteers.
The cottage-style filling station was built in 1933 and pumped gas until 1999, making it the longest operating gas station along Route 66.
There are picnic tables and wayside exhibits, including highlights of Dwight’s other historic spots. Head into town to see a Frank Lloyd Wright–designed bank and the Chicago and Alton 1879 Railroad Depot, home to the Dwight Historical Society Museum.
The Standard Oil Gasoline Station in Odell is one of the reasons to skip I-55 and drive the original route. Built in 1932, this restored landmark is on the National Register of Historic Places.
Not ten minutes away is another quick photo op: an advertisement for Meramec Caverns on the side of a barn. There’s even a pull-out so you can get a decent photo.
The next community is a centerpiece of the Route 66 in Illinois experience. Pontiac truly celebrates the Main Street of America, with lively murals, six wayside exhibits, and the Route 66 Association Hall of Fame and Museum.
Don’t miss the 1875 Livingston County Courthouse, a gorgeous red and white building restored in 2012.
Abraham Lincoln, memorialized with a statue on the south side of the building’s square, frequently visited the previous courthouse prior to his presidency. The building is listed on the National Register of Historic Places.
Be careful as you drive through Towanda; one old route alignment is called Dead Man’s Curve, and for good reason. The sharp turn was only eighteen feet wide, and caught many road-trippers unawares.
Related: don’t miss these road trip essentials
It won’t be long after you’ve rounded that bend that you’ll be in Bloomington–Normal. These two-for-the-price-of-one cities have a few things going for them.
There’s Sprague’s Super Service Station, a two-story Tudor revival built in 1930–31 that now houses a gift shop and information center; the Cruisin’ with Lincoln on 66 Visitors Center inside the McLean County Museum of History; and Miller Park Zoo.
If it’s time to replenish your road trip snack stash, stop in at the Beer Nuts Factory and Company Store.
If you’re driving Route 66 in Illinois from March through August, pull into Funks Grove Pure Maple Sirup. The Funk family has been tapping sap since 1824. Why is it spelled with an i instead of a y?
In the 1920s, the preferred spelling according to Webster’s Dictionary was “sirup,” and when Hazel Funk died, she requested that the family company continue to abide by Webster’s recommendation.
Atlanta, population 1,619 in 2018, may be a small town, but it’s big enough for a Muffler Man. One of the most well known Route 66 Illinois attractions is Bunyon’s Statue—another one of the route’s giants.
Originally located at Bunyon’s hot dog stand in Cicero, the nineteen-foot-tall man holding a huge hot dog now has his own plaza in Atlanta.
After getting a look at the bun-toting giant, loosen up your limbs with a visit to the Route 66 Arcade Museum, which is packed with old pinball and video games.
On your way out of town, check out the Atlanta Public Library and Clock Tower. Built in 1908, it’s one of few octagonal libraries in Illinois.
Your next community is Lincoln, the only town named for the President while he was still living.
Downtown, the Courthouse Square Historic District is a time capsule; most of the buildings are at least 100 years old. In the center of the square is the Logan County Courthouse, built in 1905.
A visit to the Postville Courthouse State Historic Site is another trip back in time on Route 66 in Illinois.
The building is a reconstruction, erected in 1953, and inside replicates what the original would have looked like in the mid-1800s when Lincoln used to visit.
Fans of “World’s Largest Things” won’t want to miss the Railsplitter Covered Wagon. Recognized by Guinness World Records as the “World’s Largest Covered Wagon,” the vehicle is piloted by Abe Lincoln, who sits in the driver’s seat and welcomes all to this roadside attraction.
It’s time for Springfield! You’ll want to spend a whole day in the state’s capital. In addition to being the seat of government, the Illinois State Capitol and the Illinois State Museum, this city of more than 100,000 is also home to the Illinois State Fairgrounds, Lincoln Home National Historic Site, and Abraham Lincoln Presidential Library and Museum.
If you’re hungry, visit the place that invented the corn dog; Cozy Dog Drive In has been serving up that venerable fair food on a stick since the 1940s.
Frank Lloyd Wright fans will want to tour the Dana–Thomas House, and hunters of giants will find the third Illinois Muffler Man at Lauterbach Tire and Auto Service.
Before you continue your journey, take a spin through the first drive-thru window (allegedly) in the US at Maid-Rite Sandwich Shop.
While their specialty has been loose meat sandwiches since the 1920s, this spot should not be confused with the Iowa-based chain. Even though they have the same name and a similar menu, they’re not connected.
Those trusty Route 66 signs are about to give you a real treat. Follow the pre-1930s alignment and south of Chatham they’ll direct you to 1.4 miles of Original Historic Route 66 Brick Road.
Driving this stretch, another listing on the National Register of Historic Places, is like hopping into a time machine.
The old mining town of Virden is known for more than coal; it was a hotbed of labor rights in the late 1890s. A fatal battle took place here during a mine strike, and it’s memorialized in a wayside exhibit and at Virden Miner’s Riot Memorial.
After Virden, you’ll get to drive an even older section of the route. There’s a stretch of concrete pavement that was constructed around 1920; it was originally old Illinois Route 4 before becoming Route 66.
Carlinville was also a mining town, but it had another claim to fame: bootlegging. From 1926–31, Route 66 cut through the town, bringing rumrunners and gangsters from Chicago.
Rumors have it that Al Capone himself used to secretly visit and stash liquor in an area barn.
Prior to Prohibition, another scandal rocked the town: an 1867 project to build a new courthouse, funded by $50,000 in bonds and taxes, had run up a cost of $1.3 million by 1870.
Today’s visitors can see this “Million Dollar Courthouse” and take a tour of the Carlinville Historic Square.
If you take the newer, eastern alignment from Springfield, you’ll drive through Litchfield. Catch a movie at the Skyview Drive-In, which has been screening movies since 1951 and is the last remaining original drive-in movie theater on Route 66 in Illinois.
Browse the stacks at the Litchfield Carnegie Library Building, constructed in 1904.
You can also learn about the area at the Litchfield Museum & Route 66 Welcome Center.
Make sure you grab some baked goods to go from Jubelt’s Bakery & Restaurant, which first opened in Mt. Olive in 1922 and moved to Litchfield thirty years later.
You’re nearing the Mississippi River, but there are still a few things you’ll want to check out. DeCamp Station in Staunton is an historic roadhouse that once provided all the amenities an early road-tripper could want: a place to sleep, a dance hall—and a brothel.
In 1930, gangsters robbed the place of slot machines, guns, alcohol, and cash, then escaped in their black sedan. Photos on the wall give you a glimpse of the old dance hall.
Edwardsville has been around longer than all but two other Illinois cities. Incorporated in 1818, the same year the state became official, the town has three different historic districts: the Downtown Historic District, the St. Louis Street Historic District, and Leclaire National Historic District.
Take the Historic Route 66 Spur for your final stop at the Old Chain of Rocks Bridge. With one end on Chouteau Island in the Mississippi (which is still in Illinois) and the other in Missouri, this historic crossing is now a 1.6-mile pedestrian trail.
The bridge, with its unique thirty-degree bend, is part of a network of more than 300 miles of trails on both sides of the river.
You did it! From Chicago to the Mississippi River, you’ve driven Route 66 in Illinois.
Route 66 in Illinois and more Midwest Road Trip Adventures
If you want to find even more exciting and fun trips, get your copy of Midwest Road Trip Adventures. This fun anthology was produced my members of the Midwest Travel Network and features road trips from every Midwestern state.
