Skyscrapers give way to farmland, small towns, and colorful roadside oddities as you travel south on Route 66 from Chicago. Roughly 300 miles of the epic Route 66 journey run across Illinois, slicing through an expanse of heartland that still echoes with stories of the fabled Mother Road.
Take your time in Illinois. Two days makes for a relaxed itinerary, with an overnight stay in the capital of Springfield. Or consider joining the “Miners, Mobsters and the Mother Road” caravan (June 12-14, $35 per person), an annual pilgrimage hosted by the Route 66 Association of Illinois. Road trippers get a passport book with specific stops and directions.
For the DIY types — and what is a road trip without that independent spirit? — here are Route 66 must-sees in Illinois.
Lou Mitchell’s, Chicago
This classic diner is the perfect place to load up on breakfast before hitting the road. (Photo: Lou Mitchell’s)
Lou Mitchell’s, a throwback diner from 1923, is the original starting point for Route 66 and the perfect place to load up on a big breakfast before kicking off the drive. The always boisterous ambiance includes a mix of local professionals, tourists, and Chicago cops. (When the cops like to eat somewhere, you know it’s good.) Mention that you’re driving Route 66, and you’ll get free ice cream.
Rialto Square Theatre, Joliet
The historic Rialto Square Theatre features a unique blend of architectural influences. (Photo: Illinois Route 66 Scenic Byway-Schmeeckle Reserve)
Once one of Al Capone’s favorite entertainment hangouts, the Rialto Square Theatre is considered one of the most beautiful theaters in the United States. Built in 1926, it’s a mix of Italian Renaissance, Greek, Roman, Byzantine, Rococo, Venetian, and Baroque architecture. Which begs the question — was the architect progressive or just indecisive? Take the tour on a Tuesday and find out.
The Gemini Giant, Wilmington
The friendliest giant spaceman you’ll ever meet. (Photo: Anne Swoboda/Flickr)
He’s definitely not from the Midwest. The 30-foot-tall Gemini Giant, a spaceman statue, used to welcome hungry travelers to the Launching Pad Drive-In (now closed). Today, he inspires rubbernecking and selfies.
Route 66 Association of Illinois Hall of Fame and Museum and Murals, Pontiac
The iconic Route 66 mural in Pontiac. (Photo: City of Pontiac)
Hello, photo ops! Pontiac is filled with colorful murals that capture the nostalgia of the Mother Road. Also be sure to stop in the Route 66 Association of Illinois Hall of Fame and Museum, which is located in Pontiac’s old firehouse and filled with memorabilia of bygone days. Plus, it’s free.
Funks Grove Pure Maple Sirup, Funks Grove
Nothing better than syrup fresh from the tree! (Photo: Erica Bray)
How about some fresh maple syrup? Debbie and Mike Funk continue a tradition that goes back six generations at Funks Grove Pure Maple Sirup (they use the old spelling!). In business since 1891, the family-run operation produces an average of 2,000 gallons of syrup each season. The gift shop has been remained a popular stop on Route 66, and the hamlet of Funks Grove — with its Old Country Store and Shirley Railroad Depot — offers sweet nostalgia.
Arcadia: America’s Playable Arcade Museum, McLean
From Pac-Man to pinball, Arcadia’s got it all. (Photo: Courtesy of John Yates)
Be a pinball wizard at Arcadia: America’s Playable Arcade Museum, a time capsule of a 1980s video arcade. You’ll find classics such as Donkey Kong, Tron, Ms. Pac-Man, and Super Mario Bros. Admission is free, and most games cost a whopping 25 cents to play. Want more? A second museum recently opened five miles down the road in Atlanta called the Route 66 Arcade Museum, which focuses on arcade games from 1935 to 1980. Game on!
Paul Bunyan Statue, Atlanta
The 19-foot-tall, hot-dog-toting Paul Bunyan of Atlanta. (Photo: Anne Swoboda/Flickr)
This 19-foot-tall Paul Bunyan Statue is one of Route 66’s novel Muffler Man Statues: a handful still dot the roadside of historic Route 66 in various forms. This one used to hold an axe, but it was replaced by a hot dog once purchased by a Chicago-area hot dog restaurant in 1965. It was later moved to Atlanta to inspire smiles for Route 66 travelers. (As does Atlanta’s smiling water tower down the road.)
The World’s Largest Covered Wagon, Lincoln
The World’s Largest Covered Wagon in Lincoln. (Photo: Erica Bray)
Eyes on the road, Mr. President. Abraham Lincoln reads a law book atop a 24-foot-tall wooden wagon: the World’s Largest Covered Wagon, recognized by the Guinness Book of World Records. Before making history as the nation’s 16th president, Abe practiced law and politics in Illinois.
Abraham Lincoln’s Presidential Library and Museum, Springfield
The Abraham Lincoln Presidential Museum in Springfield, Ill. (Photo: Abraham Lincoln Presidential Library & Museum/Facebook)
The official slogan for Illinois is “Land of Lincoln.” So it’s no surprise that Springfield celebrates its hometown hero with fervor. First, there’s the Abraham Lincoln Presidential Library and Museum, an immersive experience filled with cool technology and priceless historical artifacts, including the original Emancipation Proclamation. Then there’s the Lincoln Home: a four-block pedestrian area that hosts period reenactors in the summer.
Cozy Dog Drive-In, Springfield
And we all have Cozy Dog to thank for hot dogs on sticks. (Photo: Cozy Dog/Facebook)
Pay homage to the birthplace of the corn dog at the Cozy Dog Drive-In. Part drive-in and part Route 66 museum, this joint has been serving up the fried food-on-a-stick delicacy since 1949.
Henry’s Ra66it Ranch, Staunton
Henry’s Ra66it Ranch in Staunton. (Photo: Rich Henry)
The quirky Henry’s Ra66it Ranch boasts a vintage gas station. As the name implies, there are rabbits, rabbits, and more rabbits. Both the hopping kind and the VW kind. The friendly owner, Rich Henry, gets rave reviews from passersby for his knowledge of Route 66. But it’s unclear which he’s more passionate about: Route 66 or his rabbits.
World’s Largest Catsup Bottle, Collinsville
That certainly is one large catsup bottle. (Photo: Illinois Route 66 Scenic Byway-Schmeeckle Reserve)
The 170-foot-tall water tower — the World’s Largest Catsup Bottle — was built in 1949 for the plant that once bottled Brooks catsup. Named to the National Register of Historic Places, this roadside attraction even has a fan club.
For more information about traveling in Illinois, go to enjoyillinois.com.