From the neon glow of Chicago’s diners to the quirky roadside giants of Livingston and Collinsville, Illinois, sets the stage for America’s greatest road trip.
Lou Mitchell’s
Kick off Route 66 the right way, with a pancake smile! Lou Mitchell’s has been fueling travelers since 1923 with hearty breakfasts and nostalgic charm. Kids (and kids at heart) can order the famous Mitchell Mouse pancake, while women and little ones score free donut holes and Milk Duds—sorry, fellas. From skillet omelets to fluffy stacks, Lou’s is an all-American classic where neon nostalgia meets serious comfort food.
Old Joliet Prison
Part history, part Hollywood, and all intrigue, the Old Joliet Prison has seen it all. Built in 1858 by inmates, this looming limestone fortress once held infamous names like Leopold and Loeb and even John Wayne Gacy before starring in The Blues Brothers and Prison Break. Today, you can wander its eerie halls on guided or self-guided tours, or brave a nighttime flashlight tour if you dare.
Gemini Giant
Meet the Gemini Giant, a 30-foot-tall spaceman who’s been stopping traffic and filling camera rolls since 1965. Once the mascot of Wilmington’s Launching Pad restaurant, this fiberglass icon of the space race now stands proudly at South Island Park, rocket in hand and selfie-ready. Saved and restored by the Joliet Area Historical Society, the Gemini Giant remains one of Route 66’s most beloved Muffler Men.
Route 66 Association Hall of Fame & Museum
Pontiac’s crown jewel for Route 66 fans, the Route 66 Hall of Fame & Museum is a nostalgic maze of murals, memorabilia, and midcentury magic. Explore galleries filled with treasures from Illinois 66 Hall of Fame stops, 1940s Americana, and even a Titanic exhibit. The star attraction? Bob Waldmire’s legendary VW microbus, the real-life inspiration for Fillmore in Pixar’s movie, “Cars.” Outside, strike a pose by the world’s largest painted Route 66 shield (it’s practically a rite of passage).
American Giants Museum
Standing tall in Atlanta, Illinois, the American Giants Museum is a tribute to the fiberglass giants that once dominated the roadside. Inside the retro Texaco-style building, exhibits trace the story of California’s International Fiberglass Company through vintage photos, artifacts, and rare memorabilia. You’ll spot quirky creations like A&W’s Burger Family, an Esso tiger, a Uniroyal Gal head, and more. Outside, don’t miss the Paul Bunyon Hot Dog Statue and towering Texaco Big Friend.
World’s Largest Covered Wagon
Only on Route 66 can you find a 40-foot-long covered wagon driven by Abraham Lincoln himself. (Okay, it’s a statue, but still.) Dreamed up in 2001 by Illinois resident and retired police officer David Bentley while recovering from heart surgery, this Guinness World Record-holding creation was built from oak and steel as a tribute to Honest Abe. Now parked proudly in the town of Lincoln, it’s equal parts impressive, patriotic, and delightfully ridiculous.
Illinois State Fairgrounds Route 66 Experience
Cruise through the story of Route 66 without leaving Springfield at the Illinois State Fairgrounds Route 66 Experience. Open year-round, this self-guided exhibit celebrates the Mother Road’s 92 Illinois communities with vintage billboards, witty Burma-Shave ads, and a drive-in setup from the ’50s. See glowing recreations of lost neon icons like the A. Lincoln Motel and Bel-Air Drive-In in the Neon Sign Park.
Cozy Dog Drive In
Bite into a Springfield original at Cozy Dog Drive In, where the corn dog got its Route 66 fame. Invented by Ed Waldmire in the 1940s, the Cozy Dog is hand-dipped in the same secret batter recipe still used today. The Waldmire family keeps the tradition alive with a menu full of classics, including chili cheese dogs, crispy onion rings, and golden cheese curds. Surrounded by Route 66 memorabilia and Bob Waldmire’s art, it’s nostalgia served on a stick.
Downtown Springfield
Rev your engines and roll into downtown Springfield for the International Route 66 Mother Road Festival, a high-octane celebration of classic cars held every September. Watch the streets fill with chrome and color during the epic cruise parade, cheer on the burnout competition, and groove to bands that keep the energy humming. Between the car shows, pin-up contests, and local eats, this festival is Route 66 nostalgia at its finest.
Pink Elephant Antique Mall
You can’t miss it—literally. A massive pink elephant, a flying saucer, and a giant ice cream cone mark the entrance to the 30,000-square-foot Pink Elephant Antique Mall in Livingston, Illinois. Housed in a former high school, this retro wonderland is packed with quirky collectibles, vintage treasures, and photo ops galore. Outside, check out the saucer-shaped Futuro House, a Twistee Treat building, and a Bob’s Big Boy statue, then grab ice cream for the road!
World’s Largest Catsup Bottle
Behold the mighty condiment! Towering 170 feet above Collinsville, the World’s Largest Catsup Bottle is a beloved slice of roadside absurdity. Once a water tower for a bottling plant, this Route 66 icon is also on the National Register of Historic Places. It’s big, it’s bold, and yes, it’s spelled catsup. Be sure to snap a photo to commemorate the end of your Illinois adventure.
Chain of Rocks Bridge
The Chain of Rocks Bridge has been a Route 66 icon since 1929, once filled with cars and now buzzing with walkers and cyclists. Spanning the Mississippi between Illinois and the outskirts of St. Louis, it offers sweeping views and great photo spots. As your final Illinois stop on the Mother Road, it delivers a picture-perfect finish before you roll into Missouri.
