Right in the heart of downtown Chicago sits the start line of the most famous road in America. During its official life from 1926 to 1985, Route 66 carried a nation on the move, through Illinois and all the way to the Santa Monica Pier in California. Especially after WWII, Americans found themselves flush with optimism, eager to see new country and obsessed with the automobile. The road west beckoned. Illinois’ stretch of the route, now designated a National Scenic Byway, grew rich with history as generations motored through.
Though the interstate highway system replaced it as the nation’s thoroughfare, the route’s siren song still echoes. Start in downtown Chicago. From there, find your way through a patchwork of urban areas and wide-open spaces, collecting slice after nostalgic slice of vintage Americana, including oddball sights that’ll light up your social feed and meals that’ll send your eyes rolling in delight.
Journey the state’s entire 301-mile stretch, or choose a section covering your own must-do’s. Either way, with more than a weekend’s worth of stuff to see, set aside ample time to buckle in and head out on the highway.
Get pumped for your trip with our essential Route 66 soundtrack, including tracks from a few amazing Illinois artists.
Begin at the beginning: Buckingham Fountain in downtown’s Grant Park. Grab a selfie with one of the commemorative Route 66 signs nearby. Then stop for a diner breakfast at Lou Mitchell’s, a Chicago landmark that opened on Jackson Boulevard three years before Route 66. Enjoy a free doughnut hole and orange slice, and order an omelet or some pillowy pancakes.
In and around downtown Pontiac, find a growing number of murals—many by painters from the global art group Walldogs—that celebrate outdoor advertising’s early days. An iconic Route 66 shield mural adorns an outside wall of the Route 66 Hall of Fame and Museum, which traces the route’s history and offers up a slew of artifacts. Don’t miss artist and ultimate road-tripper Bob Waldmire’s converted 1972 orange VW Microbus (the inspiration for Fillmore, of Cars movie fame) and his Ultimate Hippie RV Road Yacht.
Fill up at Edinger’s Filling Station, serving melty sandwiches, salads and appetizers like bacon-laced, buffalo-sauced Sloppy Fries.
Then see a shiny 1931 Oakland, plus vintage dealer promotional items and lots of nice muscle from the ’60s and ’70s at the Pontiac-Oakland Museum and Resource Center. Admission is free, but $5 buys you a behind-the-scenes tour with the owner to see treasures not on display.
A water tower painted with a smiley face welcomes road-trippers to Atlanta, its vintage downtown packed full of fun. Admission is free at the Route 66 Arcade Museum, where many of the vintage games, dating from the 1930s to the 1980s, cost a mere quarter. Which means that if you’re an ace at Pac-Man or pinball, your money will last awhile.
Step outside and grab a pic of the towering fiberglass Paul Bunyon statue. Yes, he’s holding a hot dog instead of an axe. No, there’s no blue ox anywhere. Just go with it.
Across the street, the restored storefront of The Palms Grill Cafe looks uncannily as it did when the place opened in 1934. It still dishes comforting classics like patty melts and open-face horseshoe sandwiches (hamburger patty on thick bread smothered in fries and cheese sauce). Groove to the 1940s soundtrack as you lift your first swoon-tastic forkful of coconut cream pie.
In the capital city, meet your food-on-a-stick quota at Cozy Dog Drive In, a mainstay dating from the 1940s. Ed Waldmire Jr. created a batter-dipped hot dog on a stick, now known as your standard state fair corn dog. While at the drive-in, be sure to wander the Route 66 memorabilia collection.
Then head over to Abe Lincoln’s stomping grounds. Check out the Old State Capitol to see where Lincoln served as a legislator and delivered his famed “House Divided” speech on slavery. Examine the vast artifact collection at the Abraham Lincoln Presidential Library and Museum. Pay respects at his tomb in Oak Ridge Cemetery—for good luck, rub the well-worn nose of the bronze Lincoln bust.
Visit cutely compact Mahan’s Filling Station at its home outside Fulgenzi’s Pizza and Pasta. It’s about 100 years old and believed to be one of few such examples still standing. And cap your day with a throwback jaunt to the friendly (and affordable) Route 66 Twin Drive-In movie theater, which shows outdoor double features every summer night.
If you drive the entire Illinois stretch from Chicago, your journey may conclude at Chain of Rocks Bridge. The mile-long span famous for its 30-degree bend once carried Route 66 drivers over the Mississippi River. Now open only to cyclists and pedestrians, the bridge proves an apt (if not particularly subtle) symbol of where we’ve been, how we got there and where we’ll head to next. Which, really, is the essential magic of Route 66.
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