Ready to explore the Illinois stretch of Route 66? In this article, Gary Crallé shares his simple five-day, 301-mile road trip plan from Chicago to St. Louis, with can’t-miss stops, charming small towns, and classic roadside attractions to watch out for.

Illinois Route 66 Attractions — Mile per mile, Illinois has more Route 66 attractions than any other state. Photo Credit: Gary Crallé.

In 2004, I made a 60-day driving trip through 14 states as my baptism into digital travel photography. It was an important stage in my life, propelling me forward to discover the world in new and exciting ways. Ideally, life is about exploring the possibilities, and Route 66 became part of mine.

Route 66 is likely the most famous road in the United States. It’s a cross-country journey that takes you from one experience to another. The 5-day road trip outlined here highlights some of the best attractions along the 301 miles of the Illinois portion of the route from Chicago to St. Louis.

Consider this blog a jumpstart; ideally, you will take time to pursue your own interests. That’s the great thing about road trips: they touch on everything. So start your engines, ladies and gentlemen. Get ready to get your kicks all over this meandering strip of hardtop, once proclaimed “the Main Street of America,” as it celebrates its 100th birthday in 2026.

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100 Years of Route 66 & How It Became Famous

As part of the first federal highway system in the U.S., Route 66’s initial claim to fame was being the ‘shortest, best and most scenic route’ from Chicago to Los Angeles. The year was 1926, and its reputation has since grown to mythic proportions. The reason? It’s classic Americana where timeless nostalgia meets the constant quest for something new—a road map of the American psyche.

John Steinbeck gave it “Mother Road” status as the route taken by poor Dust Bowl farmers heading west to fabled California in his Depression-era novel The Grapes of Wrath. When the novel was made into a movie in 1940, it was the first of several films exploring the twin themes of opportunity and self-discovery. Easy Rider (1969), National Lampoon’s Vacation (1983) and Forrest Gump (1994) have all included the road as an integral part of their stories.

Route 66 began to really take off in a leisurely way, so to speak, in post-World War II car-hungry America. Songwriter Bobby Troup’s 1946 song “Route 66” and numerous renditions, including those by Nat King Cole, Chuck Berry and the Rolling Stones, helped popularize the road.

As the 1950s interstate highway systems brought an end to the glory days, Route 66 drifted into nostalgia and excitement just as the Baby Boomers were coming of age. The romantic image of the Mother Road has been in fifth gear ever since.

TV was a big factor propelling Route 66 to stardom. Shows like the 1960s TV series ‘Route 66’ with a couple of cool dudes travelling the road in a Corvette convertible added enormously to the glamour.

Small towns may have withered, but the fame continues. So does much of the road, although often rerouted, repaved and sidelined by the fast lanes of modern life. What remains is a revered thread of baubles and jewels, tarnished or polished, that reflect an era. These attractions offer a window into recent history, are often unabashedly kitschy and tourist-trappy, but always insightful and fun.

It’s a joy to see them beautifully preserved and restored as the 2026 centenary rewinds the clock. To celebrate 100 years of the route, special events are also planned along its entire 2,448-mile / 3,940-kilometre route from Chicago to Santa Monica, California this year.

How To Plan Your Road Trip Down Route 66 & Where to Stay

For various reasons, there are confusingly no fewer than four signs in separate locations proclaiming the start of Route 66. However, the “BEGIN” sign at 77 East Adams in front of the The Art Institute of Chicago is considered the official one.

My suggestion? Get a map, either electronic, paper, or both. I found the free Route 66 Ultimate Guide app useful; it is available in the Apple Apps and Google Play stores. You’ll find several other apps listed online. For those who prefer a wider view, AAA/CAA publishes a dedicated paper map of the entire cross-country route.

The Illinois Office of Tourism groups the Illinois Route 66 attractions into three areas. The first hundred miles is known as Heritage Corridor, the next stretch is the Springfield (capital) region, with the final section known as Great Rivers and Routes.

Where to Stay on the Route

There are plenty of places to stay along the route, for both the quirky-minded, nostalgic traveller and more typical rest-your-head kind of stays.

During my trip beyond Chicago, I stayed in Pontiac at the Best Western Pontiac Inn, in Springfield at the Crowne Plaza Hotel, and in Collinsville at the Doubletree by Hilton. Each spot was well appointed, and a good place to rest my head after a day on the road.

If you’re looking for more nostalgic places to stay along the route, The Ohio House Motel (Chicago) and The CarlinVilla Motel (Carlinville) are options you can look into.

Illinois Stops Along Route 66 Start With at Least One Day Chicago

Let’s start at the beginning: Chicago. For six years running, this pulsing metropolis has been voted Best City in the USA by Travel & Leisure readers. It’s a brawny, friendly place that does things on a grand scale with a sense of class.

Boat tours on the Chicago River are a perfect introduction to this “City of Big Shoulders.” For the past three years, the Chicago Architecture Center (CAC) River Cruise aboard First Lady has been chosen No. 1 Best Boat Tour in the nation by USA Today.

CAC’s elegant white vessel was ready with a full group for its sunny afternoon 90-minute tour as I boarded at the Michigan Avenue and Wacker Drive dock site. The volunteer docents are extremely knowledgeable and entertaining. Our guide, Eric Patton, was an exceptional narrator whose stories brought to life the monumental edifices lining the river.

Land tours are another good entrée to the city. I hopped aboard a Route 66 trolley tour by Mike McMains, an energetic guide with a wealth of information about architecture, design and history. Mike’s tour took us through neighbourhoods and past landmarks with enduring connections to Route 66, starting with Lou Mitchell’s Restaurant, whose breakfasts have launched countless motorists down the road.

We rolled through Douglas Park, stopped at a Dr. Martin Luther King Jr. landmark, did a Chess Records drive-by, and much more. We sang and danced in our seats when Mike played renditions of the Route 66 music theme, from Nelson Riddle to the Rolling Stones, who, coincidentally, began as a Chicago Blues band.

If you’re looking for more ideas for how to fill your time in Chicago, be sure to read our full guide here.

Day 2: Joliet to Pontiac, Illinois

Old Joliet Prison, Joliet, IL

It was outside the walls of Old Joliet Prison that paroled convict Jake Blues (John Belushi) met up with his brother Elwood (Dan Aykroyd) in the 1980 film The Blues Brothers. The filming was a secret project, although interestingly, at Belushi’s insistence, some of the prisoners took part in the production.

On my tour of the prison, I learned that the 1858 “World’s Toughest Prison,” aka “a hell hole,” was, according to a former warden, built like a castle where the warden was king. These days, it’s open for tours and special events like screenings of the Blues film. You can also say hello to the lifelike replicas of Aykroyd and Belushi inside the entrance.

More Stops from Joliet to Pontiac

The Illinois Rock & Roll Museum is a jam-packed corner of music memorabilia, much of it related to Route 66, celebrating the rich legacy of Illinois. It’s a non-profit organization whose museum membership includes partner membership in NARM (North American Reciprocal Museum) with free access to member institutions across Bermuda, Canada, the Cayman Islands, Puerto Rico, Mexico, and the United States.
At Nelly’s Restaurant on Route 66 in Wilmington, I chowed down on a lunch of chips, a burger and beer from Old School Brewing.
Across from Nelly’s, the Gemini Giant is a 1960s roadside muffler man celebrating the Gemini space program, featuring a rocket ship and a pseudo welder’s space helmet. I came across muralist Robert Ryan as he added the finishing touches to the adjacent Landing Pad Souvenir Shop. His work replicates numerous projects along 66.
Ambler’s Texaco in Dwight is the longest-operating gas station on Route 66. This gas station served travellers for 66 years before closing in 1999. It’s been refurbished as a welcome center staffed by volunteers. Hop into the 1914 fire engine for a selfie.

Illinois Route 66 Hall of Fame & Museum, Pontiac, IL

The Illinois Route 66 Hall of Fame & Museum in Pontiac compacts the history of the Mother Road with so many items that it boggles the mind. Peep into artist Bob Waldmire’s travelling VW studio vans both out in the parking lot and indoors. Outside is where you’ll also find the route’s largest shield mural on the back wall.

Before modern billboards, “walldog” sign painters applied their talents to all sorts of buildings—and Pontiac is no different. Much of this street art can still be found, faded and peeling on exterior walls, along with some striking new creations.

At Bob & Ringo’s Grill, where I stopped in for dinner, an elk trophy surveys the substantial bar that sports a sign saying ‘No sniveling.’ BBQ chicken was my go-with-the-flow choice.

Day 3: Atlanta to Springfield, Illinois

The American Giants Museum, Atlanta, IL

The American Giants Museum in Atlanta is a fun and quirky stop. It’s a museum of literal giant statues from a bygone era. We arrived as a jumbo Viking was being hoisted into place.

Bill Thomas of the Atlanta Betterment Fund gave me a backgrounder. Texaco had 300 giants manufactured in the 1960s, then ordered them destroyed due to fallout from both the dealers and the public. Dealers were required to move them from station to station, but they kept falling over, and there were public complaints like, “He’s looking in my window.”

Six giants are on loan to the museum (including Paul Bunyan). And to clear up one giant misconception: Although he looks similar, the property’s Snerd giant is not Alfred E. Neuman from MAD magazine, but is named after one of comedian ventriloquist Edgar Bergman’s dummies, Mortimer Snerd.

Carpenter Park, Springfield, IL

If you stop at Carpenter Park in Springfield, you can walk the original road (if only for 15 minutes end to end). This 90-year-old quarter-mile stretch of the highway was hidden until it was cleared to create a walking path within a nature preserve. It was only in use for about 10 years before 66 was realigned, so you’re treading on the original surface.

Illinois was the first state to claim a concrete “slab all the way” road surface back in 1926. This is one of the few remaining portions. A handful of descriptive signs provide some history. Did the Romans actually erect the Route 66 sign in Roman numerals? Candid answer: The road isn’t that old.

After a walk, it was definitely time for lunch. I have to admit, I was skeptical, but after first grooving to the music on the outdoor Illinois 66 speaker sign at the Cozy Dog Drive-In, I stepped inside the retro diner to order a cozy dog, and liked it. This is one of three places that claim to have invented corn dogs by deep-frying a hot dog coated in cornmeal batter. I haven’t tried the others, but I can vouch that the Cozy Dog has the flavour.

The Pharmacy Gallery & Art Space, Springfield, IL

Bob Waldmire was an artist and cartographer known for his whimsical maps and artwork of Route 66. It was his father who created cozy dogs.

With this in mind, I stopped to enjoy the Bob Waldmire exhibit at the Pharmacy Gallery & Art Space. As a nomadic hippie, Bob roamed the highway in his ’72 VW van, his “studio-home-on-wheels," becoming a legend in the process. The intricate detail he put into his maps is cartography on steroids.

Abraham Lincoln Presidential Library and Museum, Springfield, IL

My next stop was the Abraham Lincoln Presidential Library and Museum. It offers an immersive experience into the life and legacy of America’s 16th president. State-of-the-art multimedia and original artifacts bring you through Lincoln’s early years, his presidency and the Civil War. It’s all well done and worth the stop.

Motorheads, Springfield IL

Ron and Pat Metzger are a husband-and-wife team best known (in the Route 66 world) as the owners behind Route 66 Motorheads Bar & Grill, Museum & Entertainment Complex in Springfield.

The couple bought and renovated this 1970s complex, including a former Stuckeys restaurant, to share Ron’s love for car memorabilia and Springfield nostalgia. Opened in 2018, Motorheads has since become a well-known Route 66 bar, grill, museum and party place chock full of vintage signs, motor gear and even an old gas station. It’s a great place for motor racing enthusiasts. Why else would Ron park his 1969 Chevy Camaro in the rafters?

Day 4: Springfield to Granite City, Illinois

Ace Sign Museum, Springfield, IL

Neon signs are as much a part of Route 66 as cars and peculiar motels. If you’ve ever wanted to know what goes on behind those signs, the ACE Sign Museum Tour is a unique experience. The ACE Sign Company provides free guided tours Monday to Friday at their Springfield headquarters museum. It was a gas (ahem) learning about the history of neon and the Mother Road while surrounded by classic signage.

Their biggest sign was making Roman numerals (XLVIII) 14 feet tall and 30 feet wide for Super Bowl 48. I learned that ACE wasn’t too disappointed at missing the next game assignment two years later, as it only called for the letter L.

Forty-five minutes down the road, it’s time for lunch at the Ariston Café, which proclaims to be “the oldest continuously operated restaurant on Route 66.” The rooms still exude an authentic mid-century dining “feel.” Portions are hearty, and the desserts are what your mother would have made. Did I mention all you can eat weekly specials? Since 1924.

Worldwide Technology Raceway, Madison, IL

On race days, the Worldwide Technology Raceway (WTR) course hosts top events like NASCAR, INDYCAR, NHRA drag racing and Formula DRIFT. The grounds include a 1⁄4-mile drag strip, 1.25-mile speedway, road course, kartplex, and golf links.

The raceway has over 300 events each year, sometimes as many as five in one day. One of its biggest attractions is a 2-mile Christmas lights circuit synchronized to music. The entrance is at the Route 66 sign off Collinsville Road, which was part of the original Mother Road. To promote awareness of the Road’s centennial, WTR created a Celebration of Route 66 (Music) Fest last June, combining INDYCAR action and rock music legends.

The Electric Neon Sign Park

After checking into the local Doubletree, we headed to Granite City’s newest attraction: the Electric Neon Sign Park. The signs lit up to the beat of golden oldie songs belted out by a well-practised local band. A larger-than-life Graniteware tea pot, Tinker Toy and a kid-size Old Chain of Rocks Bridge recall the heady days of Granite City’s industrious past. Vintage neon signs of bygone businesses seconded that.

As a sign of the times (so to speak), bittersweet memories of good times gone by are what characterize much of Route 66 today. But the music was good, and I was about to start my own sock hop right there in the park when I was called to dinner.

Nearby Jerry’s Cafeteria is a no-frills restaurant where the food is simple and ample, and the price is right. Daily specials are posted on Facebook where Jerry has more followers than he could ever feed.

Soon I was called away again—this time to a guarded meat locker door. The right password (I’d been tipped off) gained entrance to the secret 1920s Speakeasy, where the ambiance was, well, easy. Tiffany lamps, hand-crafted cocktails and karaoke renditions of Frank Sinatra’s ‘Chicago’ hypnotized my Route 66-laden hypothalamus, capping another good day.

Day 5: The Final Stretch to Grafton, Illinois

Livingston to alton, IL

The Pink Elephant Antique Mall (who isn’t going to stop for a pink elephant?) is home to 50 antique dealers purveying their wares inside a former school gymnasium. You could easily amuse yourself here for several hours. Aside from a prominent pink elephant figure, other characters flank the entrance, including a giant Donald Trump beside a T-Rex. “Not a political statement,” says the sign.
The West End Service Station in Edwardsville is a spic and span gas station as clean as the dental offices that occupied this site for 55 years until 2019. It’s been fully restored by the Great Lakes and Rivers Tourism Bureau as an interpretive center for those yesteryears from 1927.
The Old Herald Brewery & Distillery is turning the pages on the site of the Collinsville Herald newspaper as it concocts some fine beverages within those walls. We paired our lunch with brews with names like Proofreader Pale and Printer's Ink as an ode to the past. They’re creating a growing batch of interesting new flavours. The approach is to make drinks “smooth and sippable without the sting,” says distiller Derik Reiser. This includes everything from a horse radish vodka to agave.
Our next stop? The World’s Largest Catsup Bottle. Restoring a 70-foot-tall catsup bottle water tower sitting on a 100-foot stand was a tall order requiring much research and fundraising. Wind, rain, hail, and thunderstorms, along with lead paint, posed challenges, but the restoration of this American icon was finally completed in June 1995. It's even trademarked "The World's Largest Catsup Bottle" and listed in the National Register of Historic Places. In case you were wondering…despite its 640,000-bottle capacity, there’s nothing inside.

Tour Alton’s Landmarks, Alton, IL

Alton has witnessed at least three unusual events, commemorated by landmarks in town. Legendary jazz trumpeter, bandleader and composer Miles Davis shared his 1926 birth year with Route 66. The town continues to honour Miles with a full-size statue, one of only three in existence.

Further back, an 1858 U.S. senatorial campaign between Abraham Lincoln and Stephen Douglas focused on whether slavery should be decided by Congress or individual states. If not settled, Lincoln predicted civil war.

In more recent times, Alton was home to Robert Pershing Wadlow, the world’s tallest man, who lived a tragically brief life. Robert was a normal-sized baby, but grew rapidly due to an overactive pituitary gland. He was 5 feet tall by age 5 and outgrew his father by age 8. Robert died at the age of 22 in 1940 from an infection caused by a poorly fitted brace, unable to survive due to having an autoimmune disease. By then, he was 8’11” / 2.72 meters tall and still growing.

Aerie’s Resort & Attractions

Our final Illinois stop was Aerie’s Resort & Attractions in Grafton. Whizzing downhill between trees on a roller coaster built for one sure takes your pulse up a notch. The Alpine Coaster is a first in Illinois. Paired with Aerie’s chairlift (SkyTour) and the Terrace restaurant, it’s a great way to enjoy a panoramic view at the confluence of the Illinois and Mississippi Rivers—yet another way to experience something new along the Mother Road.

Route 66 continues on through St. Louis, Missouri, but let’s save that for another story.

Gary was hosted as media by Visit the USA for this trip along Route 66. All thoughts and comments in this article are entirely his own.

Illinois Route 66 Attractions: The Ultimate Road Trip Guide from Chicago to St. Louis