A Historic Route 66 Road Trip Across Illinois: Driving from Chicago to St. Louis

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One of the most famous thoroughfares in the world, “The Mother Road” or the “Main Street of America” is a designated national scenic byway that runs from Chicago all the way to Los Angeles. Built in the 1920s, it was one of the first major transcontinental routes in the U.S. and covered nearly 2,500 miles across eight states.

At its inception, the trip represented the hopes, dreams, and curiosity of what existed west, a journey of uncertainty and possibility. But over time, the road took on the mood of the nation with remnants from the Great Depression-era through the traditional values of the ‘50s and even to the free-spirited, vagabonding ‘70s that feels like you’re driving back in time through the decades.

The Illinois portion stretches clear across the state for 300 miles and is a great introduction into its nostalgia: the antique signs, vintage cars, quirky roadside attractions, and kitschy memorabilia of America’s heyday that provide an interesting look into the golden era of travel. Truly about the people you meet, many of the businesses are family-run and multi-generational with owners who pride themselves on memorializing the way things used to be — by talking to passersby’s. They are as curious to hear your experience as they are to share their own story.

Whether you’re a history buff, motorhead, photographer, road trip enthusiast, or general travel lover, driving Route 66 is a trip everyone should have on their Chicago bucket list and take at least once in their lifetime. Because it’s always about the journey as much as the destination. Here’s an easy itinerary to follow and everything to look out for along the way:

Chicago

The “Route 66 begins” sign is on Lake Shore Drive and East Jackson Boulevard in Grant Park. But where it actually begins is up for debate as the official start has moved a few times. Currently, the route starts at Adams Street and Michigan Avenue due to land being reclaimed by the World’s Fair and Jackson becoming a one-way street the wrong way. Regardless, snap a photo by the iconic marker and enjoy some of the Windy City’s best attractions.

Do

For skyline views, head up to the Skydeck of the Willis Tower which looks out over the 103^rd floor or to 360 Chicago, the crazy, tilted glass observation platform in the John Hancock building. Wrigley Field and Navy Pier are other iconic attractions if time allows.

Eat

Since opening in the late 1800s, Lou Mitchell’s has been many’s first stop on Route 66. One of Chicago’s OG breakfast spots, they boast the area’s best coffee and were the place to fill up and get the caffeine pumping before hitting the road. Right in the city, the Berghoff is another historic institution. German food that gained popularity during the prohibition era, they’ve been dishing up sandwiches and beers for over a century. On the way out of town, Dell Rhea’s Chicken Basket is another iconic gas station lunch counter turned dining room that’s withstood the test of time. Featured in a number of Route 66 documentaries and write-ups, their fried chicken is some of the best of the land.

Photograph

Grant Park is home to many of Chicago’s best museums (like the Art Institute), Cloud Gate aka. “The Bean,” and Buckingham Fountain so you can get all your stereotypically touristy shots in one fell swoop.

Stay

Hotel Chicago (formerly the Rosemoor Hotel) and the Midland Hotel (now the W City Center) are two of the last remaining original Route 66 hotels.

Joliet

A little over an hour south, Joliet is part of Illinois’s Heritage Corridor. Once an industrial enclave, it’s known as the “City of Steel and Stone,” and is an interesting mix of old and new. Famous for its race track, the prison from Blues Brothers, and one of the most beautiful theaters in the nation, it truly is a place of contrast.

Do

Old Joliet Prison. The 16-acre penitentiary was built in 1848 by 50 prisoners and looks like a castle. Essentially a city within a city, there are over 20 buildings on campus that you can tour (yes, it’s extremely haunted). Part living museum, part dilapidated construction site, it’s been featured in a number of Hollywood productions like Prison Break and Empire. If you’re into cars, Route 66 Raceway is also one of the premier drag racing venues in the country and hosts fun events like demolition derbies.

Eat

Joliet Route 66 Diner is your quintessential mid-century diner with booths and “blue plate specials.” For something totally different, Chevere Latin Café offers Venezuelan specialties (similar to Cuban cuisine) with an epic Route 66 mural inside.  

Photograph

The “Jewel of Joliet,” the Rialto is an insanely gorgeous theater and vaudeville palace with a rotunda modeled after the Pantheon in Rome, an archway designed to look like the Arc de Triomphe in Paris, and an esplanade inspired by the Palace of Versailles.

Roadside Attractions En Route

The 2-Cell Jail is quite the contrast from the last prison and right next to the Street Car Diner. The Polk-a-dot Drive In, the Gemini Giant (in front of the Launching Pad Diner), and the Ambler Becker Filling Station, one of the iconic old gas stations, are also in the vicinity.

Pontiac

Continue south for another hour and you’ll reach Pontiac, Illinois’s unofficial Route 66 headquarters. A mix of murals, museums, historic homes, and swinging bridges centered around a charming Main Street and Town Square, it’s one of the cutest small towns I’ve seen in awhile. And despite common confusion, the city name has nothing to do with the car manufacturer.

Do

The Route 66 Hall of Fame & Museum is the most comprehensive collection of Route 66 memorabilia in Illinois and possibly the country. Two museums and five exhibits in one maze of a building that used to be City Hall, you’ll learn about everything from the period from life in the ‘40s to the Titanic and the Civil War. The highlight is Bob Waldmire’s hippie van and “Land Yacht.” A converted school bus you can tour, the bus is where he lived (as the OG van lifer) while driving up and down Route 66 selling his artwork, maps, and illustrations. Quite the character, he inspired one of the personalities in the movie, Cars and his family famously owns the Cozy Dog Drive-In (which we’ll get to later), despite being a vegan. He was also bizarrely arrested for transported rattlesnakes across state lines. The Pontiac Museum is also a must for classic car enthusiasts.

Eat

The Old Log Cabin is classic American fare with home cooking and freshly made pies in a rustic, no-frills dining room.

Photograph

Pontiac has15 miniature art cars and 28 murals all painted by local artists. Follow the red footprints on the ground to make a self-guided mural tour or the blue footprints to visit each of the museums. The iconic shot with the largest Route 66 insignia in the nation (and where you can pose with your car on the original bricks) is in the parking lot behind the museum.

Stay

The Fiesta Motel is one of the last remaining original, untouched motels from the ‘30s, while the Palamar Motel, built in the ‘40s and rebuilt after a fire in the ‘60s, retains its vibe from the later era. Of course, there are also contemporary options in the area if you prefer more more modern amenities.

Roadside Attractions En Route

Paul Bunyan Statue (check out the gift shop across the street for tons of memorabilia), Atlanta Arcade Museum

Springfield

The state capital and longtime home of Abraham Lincoln, many only visit Springfield on school field trips. Bizarrely, I’d never been there. And while not a history buff by any means, I found the experience surprisingly engaging. They try to make history come alive through costumed characters and by sharing quirky tidbits about his personal life. Like did you know he was the only president to be inducted in the wrestling Hall of Fame and had six cats? In the summer, reenactments take over the town showing what life was like in the nineteenth century.

Do

Presidential things. See why Illinois is known as the “Land of Lincoln.” The Lincoln Museum is very interactive with a 3D theater and hologram show. Touring his home (a National Historic Site) and visiting the tomb are also musts. It’s full of symbolism with corn stalks commemorating how he helped to create the Department of Agriculture, along with stars representing the number of states in the union and signifying he was the 16th president. In the summer, Knights Action Park and Route 66 Drive-In are wholesome family fun. A third-generation entertainment complex that just keeps expanding, it’s a movie theatre, water park, and mini golf all in one. If you’re into advertising like I am, you can also tour Ace Sign, the company that produced many of the original Route 66 signs. You’ll learn about the manufacturing process and hear how companies are migrating from vintage neon and porcelain to modern LEDs and 3D printing.

Eat

A newer Route 66 establishment, Motorheads basically outgrew the owner’s garage so he decided to share his memorabilia with the world. A bar/restaurant with an attached museum, there are race cars, a gas station, and period signs. That seems to be a theme of a lot of the people I met, collectors here would be hoarders anywhere else because they just find their way into stuff with collections that just keep growing. The Cozy Dog is another Route 66 Institution, owned by the Waldmire family (and currently run by Bob’s brother). The original hot dog on a stick, the cozy dog is said to pre-date the corn dog, but don’t even try calling it that. They’ll look at you like you’re crazy and for the record, the battering is different since it’s not fried in corn. The interior has a library of books and showcases Bob’s artwork from the road.

Foodie Tip: If you like to eat local, a signature menu item to look out for is the horseshoe. Essentially an open-faced sandwich on thick Texas toast, it’s piled high with meat and a mountain of cheese fries that is said to resemble a horse’s hoof and nails (D’Arcy’s Pint’s is award-winning). Butter cake from St. Louis is another regional delicacy down south and exactly what you imagine it to be.

Photograph

Mahan’s Filling Station at Fulgenzi’s. The Lauterbach Giant. Sugar Creek Covered Bridge. The original 1.4-mile hand-laid stretch of brick road, which is listed on the National Register of Historic Places.

Stay

Route 66 Hotel and Conference Center was the first Holiday Inn on Route 66 and has an attached gaming center. For a more comfortable, modern experience the State House Inn overlooks the capital.

Roadside Attractions En Route

Doc’s Soda Fountain. An old soda jerk that started as a 1800s drug store, many of the original pharmacy relics and Coke memorabilia are on display. Henry’s Rabbit Ranch is also one of the quirkiest stops on Route 66. Home to 60+ live bunnies and dozens of VW Rabbit cars, there’s also a rabbit graveyard, a giant bunny statue, and their makeshift version of Carhenge. The “hare emporium” truly has to be seen to believed (but visits are by appointment only).

Collinsville / Alton

The last section of Route 66 before you cross into Missouri, this part of Illinois is known as Great Rivers and Routes because it’s where the Mother Road meets the Great River Road, another National Scenic Byway. In the summer there’s a wealth of natural attractions at the confluence of America’s three great waterways. On Route 66, it was where the miners and mobsters got their kicks.

Do

The Cahokia Mounds are the largest and most sophisticated prehistoric Native American site in North America. Explore the archeological remains of one of the earliest civilizations that has all characteristics of a developed city (except written language) that was once as densely populated as London. The Pink Elephant Antique Mall/ Twistee Treat Diner is everything you love about Route 66 all under one roof. Part antique mall, part photo op, candy store, fudge shop, diner, and soda fountain, you could spend hours getting lost in the maze of trinkets and tasting sugary treats.

Eat

Weezy’s Route 66 Bar & Grill. The quintessential American burger joint, Weezy’s has been a popular dive since the ‘30s. Ariston Café is one of the longest continually operating restaurants on Route 66 and offers a range of fare from Italian to Greek.

Photograph

The World’s Largest Catsup Bottle, Litchfield Museum & Route 66 Welcome Center, and Chain of Rocks Bridge, a one-mile pedestrian bridge where you can walk across the Mississippi River into St.Louis.

Stay

The Quality Inn Litchfield Route 66 is conveniently located near the Litchfield Museum.

Route 66 Road Trip Tips

What is Route 66?

Route 66 is one of the most famous roads in America and maybe the world. It was one of the first major cross-country routes in the United States and runs through eight states: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California. It is still drivable, but despite how maps make it seem, it’s not a straight shot down one highway. Parts of the road still exist. Some sections are gone. Some run alongside the present-day interstate and some detour well off the most direct path. Some portions even have three different routes where the road was moved between decades. What I came to learn is that driving Route 66 is more of a mentality than an actuality. Worry less about being on the actual road and take in the feeling of following in the footsteps of so many before you.

How Long Should You Spend Driving Route 66?

As long as you want. Some people do the entire trip in as little as a week, but at that point you’re rushing through it and not stopping to appreciate the quirks. It’s more common to take 4-6 weeks to complete the whole route from Chicago to LA. You can do the Illinois portion in as little as 66 hours if you’re ambitious, but 4-5 days is more realistic to see everything.

Do You Need to See All of Route 66 or Which Section is Best?

It’s personal preference whether you want to drive the entire road, but each section has its own vibe and appeal. For example, the Midwest is much different than the Southwest, which has a lot of scenic desert-scapes (including a town with more burros than people).

When’s the Best Time of Year to Drive Route 66?

Summer is definitely the high season, but the shoulder seasons of spring and fall are nice too and will likely have good weather and fewer tourists. While some of the Western states are warm year-round, winter in the Midwest is not ideal if you’re not accustomed to driving in snow and it starts to get pretty cold come November.

Tips for Driving in America:

Since many international visitors make the trek, there are important things to note about driving in America. If you have a valid driver’s license from your home country or an international driving permit and a credit card, you should be able to rent a car in the USA. Most rental car companies require you to be at least 21, with discounts if you’re over the age of 25. Your rates will be affected by fuel (whether you choose to return the car full or empty), how many drivers you will have, and whether you are opting-in to vehicle coverage. You’ll want to consider if you need a one-way rental (which is generally more expensive) or be willing to return the car to its point of origin (which will take longer). Make sure you have car insurance whether it’s through your personal provider or purchased as a supplement. Drive on the right side of the road and adhere to all posted signs and speed limits, which vary in each area.

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