Epic Illinois Road Trip: Exploring the Heart of Route 66’s First 100 Miles

Rediscover the Magic of the Mother Road

Originally Published September 12, 2023. Updated September 8, 2026.

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Chicago to Pontiac covers the first 100 miles of Route 66 in Illinois, and it packs in nearly every reason people fall in love with the Mother Road: roadside giants, small town museums, retro diners, and murals that turn a drive into a scavenger hunt. In 2026, we celebrate the 100th anniversary of Route 66, and there’s no better time to plan your own stretch of this legendary highway.

As someone who lives not far from Route 66 in Oklahoma, the pull of this iconic highway has always been part of my life. I’ve traveled its historic path in sections rather than all at once, savoring each stretch at my own pace. That’s the beauty of a Route 66 road trip. You can tailor the experience to fit your family, your timeline, and your sense of adventure.

Whether you have a single day or a full weekend, I encourage you to use this guide as a starting point and build your own version of the first 100 miles.

The History of Route 66: A Highway of Dreams

Route 66 officially began in 1926, when the federal Bureau of Public Roads launched it as part of the nation’s first federal highway system, stitching together existing local and state roads into one continuous route stretching roughly 2,400+ miles from Chicago to Los Angeles across eight states, according to the National Park Service.

The road quickly became a lifeline during the Great Depression, carrying Dust Bowl families west in search of work and a fresh start, and it earned the nickname the Main Street of America as small towns along its path built their economies around the travelers passing through.

Its heyday brought a boom of motels, diners, and offbeat roadside attractions, turning the drive itself into part of the adventure. That began to change in 1956, when President Eisenhower backed the creation of the modern interstate highway system. Over the next three decades, new interstates gradually replaced Route 66 as the fastest route west, and the Mother Road slipped into decline. Today, dedicated preservation groups and a wave of renewed interest have brought much of its original spirit back to life, which is exactly what makes a drive through Illinois in this centennial year feel so worthwhile.

Fun Things to See On Route 66 Illinois

Illinois’ Route 66, nestled in the heart of the Midwest, offers a glimpse of the vibrancy and diversity that this historic route embodies. It commences in downtown Chicago, and meanders through suburbs, charming small towns, and lush countryside, culminating at the state line in St. Louis.

Recently, I embarked on a 3-day road trip with friends and representatives from Heritage Corridor Destinations, the region’s tourism office. Flying into O’Hare International Airport, our journey began in Chicago and wound its way to Pontiac. Our strategy was to spend minimal time in Chicago, allowing us more time to explore the quaint towns and unique attractions that make the Illinois Route 66 an exceptional road trip destination.

Chicago – The Windy City Kick-Off to Route 66

If you’re considering a stay in Chicago to explore the city’s segment of Route 66 before venturing onto the open road, I wholeheartedly recommend adding a few days to your itinerary. Here are some family-friendly attractions to savor in the Windy City, starting at the very beginning.

Historic Route 66 Begin Sign

Our adventure begins in the bustling metropolis of Chicago. This Begin Route 66 Sign marks the official starting point of this iconic journey. You’ll find it directly in front of the Art Institute of Chicago on E. Adams Street just west of Michigan Avenue.

Standing beneath that sign is like stepping into a time capsule, filled with dreams of cross-country exploration and adventure. It’s a must-have photo for your family travel album.

Millennium Park

Just a few steps from the Begin Route Sign is iconic Millennium Park surrounded by amazing architecture, Crown Fountain, Buckingham Fountain, and “Bean” Sculpture that make for great photo ops. During the summer months, enjoy free outdoor concerts and art installations in the park.

Navy Pier

You can’t visit Chicago without a trip to Navy Pier. This entertainment complex located on Lake Michigan offers family-friendly attractions such as a 15-story Ferris Wheel, a children’s museum and so much more.

Chicago Riverwalk

Stroll along this scenic path lined with fun shops, restaurants, and vibrant public art. The Riverwalk also offers boat tours of the Chicago River and its beautiful bridges.

Wrigley Field

Take a tour of the historic Wrigley Field, home to the Chicago Cubs.

Guided Chicago Tours

If you want to make the most of your time in the city, a guided tour of whatever interests you the most is a great way to get an insider’s perspective of the city. Chicago is full of hidden gems.

1. Chicago Architecture Boat Tour: The architecture of the city is a testament to its rich history, and these tours offer fascinating insights into the city’s design and development. You’ll view some of the most iconic buildings in Chicago, including Wrigley Building, East Bank Club, and Willis Tower (formerly the Sears Tower). This is one of the top river cruises in the city.
2. Gangsters and Ghosts Tour: This tour offers an intriguing insight into the criminal underworld of 1920s Chicago. You’ll visit some famous hangouts and haunted sites that housed many notorious gangsters such as Al Capone and Bugs Moran.
3. Chicago Pizza Tour: Dive into Chicago’s culinary scene with a guided food tour that lets you sample from the best pizzerias in the city. Experience the city’s iconic deep-dish pizza and other local favorites as you venture into four different neighborhoods to truly eat your way thru Chicago.

Find Attractions and Lodging Near Me

Where to Stay:
If you’re considering spending the night in Chicago, there are plenty of family-friendly accommodations to choose from:

1. The Palmer House Hilton: This historic hotel offers luxurious accommodations in the heart of downtown Chicago, making it easy to explore the city’s attractions.
2. The Chicago Athletic Association Hotel: Located near Millennium Park, this boutique hotel combines modern amenities with a historic atmosphere, offering a unique and memorable stay.
3. The Drake Hotel: Overlooking Lake Michigan, The Drake is a Chicago landmark known for its elegance and classic charm, perfect for a touch of luxury on your Route 66 journey.

As you soak in the vibrant energy of Chicago and indulge in its culinary delights, remember that the real adventure is just beginning. Route 66 stretches ahead, promising more history, quirkiness, and family memories to be made. Stay tuned as we continue our journey through the heart of America’s most famous highway!

Chicago Suburbs – Go Wild at the Zoo

Brookfield Zoo is a great place to take the family for a day of wild, animal-filled fun. Located in the Chicago suburb of Brookfield, Illinois, this expansive zoological garden features over 511 species across 235 acres of naturalistic habitats, interactive exhibits and educational experiences.

It’s rated as one of the top 5 zoos in the country by USA Today 10BEST. Be sure to visit the iconic Great Bear Wilderness, Habitat Africa, and Living Coast. For an added experience, book tickets for the Penguin Feeding Adventure offered Friday to Sunday. It is a great way to get an up-close experience with the animals alongside knowledgeable zookeepers. On this guided tour, you’ll observe Humboldt Penguins in their habitat as they waddle and swim around. You’ll have the opportunity to feed them fish.

Burr Ridge – Pint-Sized Roadside Attraction

Just a short 45-minute drive from Millenium Park is the village of Burr Ridge. Many visitors often overlook this town. However, families traveling in the area will want to stop at Harvester Park whose southern border originally sat along Route 66.

Today Harvester Park is home to a playground filled with unique reimaginings of roadside attractions you’d find along the historic route. Children will love sliding down a slide resembling Willis Tower, popping out of the Blue Whale, riding the mini-zipline, running the path past state signs, surfing on balance boards, and more.

It’s a fun way to let the kids burn off some energy and get a taste of road-tripping nostalgia.

Willowbrook – Famous Route 66 Restaurant

Just south of Burr Ridge is the village of Willowbrook, home to a famous Route 66 restaurant – Dell Rhea’s Chicken Basket. Like many restaurants that popped up along this historic route, they were a combination gas station or garage and lunch counter. The original Chicken Basket started that way serving “secret recipe” fried chicken before it was turned into a full-service restaurant in 1946.

Today, Dell Rhea’s Chicken Basket is still going strong and serving up some of the best-fried chicken around. It’s been featured in multiple newspapers, magazines, and TV shows. Eating here is a must for any Route 66 fan looking to experience the history of the Mother Road.

If you need a break from driving, Dell Rhea’s is worth the stop. Step inside and take a seat for some delicious comfort food served with a side of Americana nostalgia.

Joliet – The City of Steel

Leaving the Windy City, we continued south and crossed into the historic city of Joliet. Known as the City of Steel for its once-thriving steel mills, Joliet is a unique destination.

Joliet Area Historical Museum & Route 66 Welcome Center

Make a stop at the Joliet Area Historical Museum to dive into this city’s unique past. The museum is home to a fascinating variety of exhibits and displays that tell the stories of Illinois’ early inhabitants, its industrial past, and the area’s future.

Here, your family can learn about the early days of Route 66 and how it became an American icon. Plus it sets the stage for other things you’ll see in Joliet like film locations for the Blues Brothers movie, the old Joliet Prison, I&M Canal, and more.

Just inside the museum is the Joliet Route 66 Welcome Center. Here you can pick up some souvenirs for friends and family made by Illinois makers. The center also provides information about local attractions and businesses along the route, so ask them questions or get recommendations if you’re looking to explore off the beaten path.

Just outside their doors is a photo opportunity site where you and your family can take a picture in front of or inside a Route 66 Sign art installation.

Old Joliet Prison Historic Site

One of Joliet’s most iconic attractions is the Old Joliet Prison, an abandoned prison that was once a hub of criminal justice in Will County. The prison operated from 1858 until 2002 and served as a backdrop to several popular movies and television shows such as “The Blues Brothers” and “Prison Break.”

After the prison closed, it fell into disrepair. But today, the Old Joliet Prison Preservation Coalition aims to restore the site and preserve its history. The site is open to the public and can take a self-guided and/or docent-led tour of the facility. You’ll be able to see the abandoned prison cells, the dining hall, the chapel, and other buildings.

Ghost tours are no longer available, but there is a Prison After Dark Tour that allows you into the prison after dark. Historical accounts told by docents add an extra layer of intrigue to your tour. It’s a perfect spot for those who love eerie experiences and are interested in the darker side of history.

Rialto Square Theatre

The opulent Rialto Square Theatre, located in downtown Joliet, is another must-see destination. The theater originally opened in 1926 as a movie palace and was restored to its former grandeur in 2003.

Located right along Route 66, the Rialto hosts Broadway shows, comedy acts, and other entertainment year-round. Be sure to check out their schedule before you come and see if there’s a performance your family would enjoy.

Joliet Route 66 Diner

This retro diner, located off of Interstate 55 and just south of the Route 66 Welcome Center, is an ideal spot for a family meal. The restaurant celebrates Americana with its classic diner decor and menu options like burgers, fries, malts, shakes, and more.

Grab a booth in this authentic 1950s-style diner and enjoy some tasty treats before continuing your journey down Route 66.

Illinois Rock & Roll Museum

The museum was not yet open when I visited (August 2023) but it is coming soon! Located on Cass Street just south of the area’s Historic Museum, this museum will celebrate the state’s rich music heritage.

It will feature artifacts from local musicians, galleries dedicated to specific artists, a recording studio, and more. During my visit, the original equipment from the WAJP FM Studio was set up and on display. Alfred and Mary Jan Phohler began broadcasting from this studio (in its original location) in 1960 through 1985.

It’s sure to be a great spot for music lovers and families looking to learn about the unique musical history of Illinois. So make sure you stop in as the gift stop is open and the museum will open soon!

Want to spend the night in Joliet? I stayed at the Wingate by Wyndham Joliet. It was very clean, had a heated indoor pool, and offered comfortable beds.

Midewin National Tallgrass Prarie

Leaving Joliet, we made a quick stop at the Midewin National Tallgrass Prairie. It is recognized as the first national tallgrass prairie and is home to over 18,500 acres of tallgrass prairie and a herd of bison. It’s an amazing place to walk, do some bird watching, or just take in the peacefulness of nature.

You can take a self-guided tour and explore the trails, view wildlife, learn about the history of this tallgrass prairie, and more. It’s an incredible sight to behold – one that must be seen in person. I highly recommend making time to stop here.

Wilmington – The Gateway to Starved Rock

Just 20 miles south of Joliet is the small town of Wilmington, IL. The town is known as the Gateway to Starved Rock State Park (not on Route 66) and the Launching Pad.

The Gemini Giant & Launching Pad

These two iconic roadside attractions are a must-stop on your journey. The Gemini Giant is a 30-ft tall metal sculpture in the shape of an astronaut created in 1965 and located at Launching Pad Drive-In restaurant.

This astronaut towers over Route 66 and makes for great pictures! The restaurant is a great spot to grab a bite when it’s open.

Braidwood – Strange Sightings

Polk-A-Dot Drive In

The Polk-A-Dot Drive In is one of the most iconic places to stop along Route 66. This roadside 1950s-style diner has been serving hungry travelers for decades. Serving burgers, ice cream, and malts, the Polk-A-Dot is a great spot for families to grab a bite.

But what really makes this place fun is the statues outside where you can snap pictures with the Blues Brothers, Betty Boop, Marilyn Monroe, Superman, James Dean, and others. Inside I had the fun experience of meeting an Elvis Presley impersonator.

Braidwood Zoo

Across the street from the Polka-A-Dot Drive-in is the Braidwood Zoo. This “zoo” is unlike anything you’ve ever seen before! This strange animal sanctuary is an art installation created by local artist Jack Barker.

His zoo, sponsored by local businesses, is all made with recycled materials and expandable foam. There’s a pink elephant, longhorn steer, giant rat, pig, and giraffe.

Dwight – Pit Stop

Ambler-Becker Texaco Station

In Dwight, stop at the Ambler-Becker Texaco Station. It was one of the oldest and longest-operating gas stations on Route 66. The station, originally built in 1933, is now a museum with vintage gas pumps, artifacts, pictures, and volunteers eager to share stories of their travels.

It’s an excellent spot to take a break from the drive and get out of your car. Plus it has a small gift shop where you can pick up souvenirs like t-shirts and postcards.

If you need to fill up your tank or grab a cold drink, there’s a modern gas station just across the street.

Need Help Planning a Family Road Trip? Start with these family vacation planning resources:

• Travel Love Language – Help to Identify, Understand, & Plan Vacations
• How to Budget for a Cheap Road Trip in 11 Simple Steps
• 25 Healthy Road Trip Snacks to Fuel Your Next Adventure
• Essential Tips for an Enjoyable Cross-Country Road Trip with Your Family
• What You’ll Need for a Fun Family Road Trip + Weekend Packing List
• Road Trip Preparation – 12 Things To Do Before You Leave, So You Can Enjoy It
• Banish Boredom with 50 Fun Road Trip Games to Play in the Car

Pontiac – Murals, Museums, and Memories

Pontiac, Illinois is roughly 100 miles from the Begin Route 66 Sign in Chicago. Illinois has 301 miles of Route 66 and Pontiac is at the end of the first hundred miles. When it comes to the heart of Route 66, Pontiac is one of the most iconic towns in Illinois. One of the things that makes it so special is its hall of fame and special exhibit on artist Bob Waldmire.

Route 66 Association of Illinois Hall of Fame and Museum

The Route 66 Association of Illinois Hall of Fame and Museum is a must-see for any Route 66 enthusiast. There are thousands of period artifacts, vintage photos, and exhibits that bring the highway to life.

Bob Waldmire Experience

One of the highlights for me was the exhibit on Bob Waldmire. Bob was a beloved Route 66 artist, cartographer, and naturalist who drove an old Volkswagen bus along the “Mother Road” from the 1970s until his death in 2009. His van was the inspiration for the Disney Cars’ character “Fillmore”.

This van, as well as, Bob’s “Road Yacht” – a 1966 modified school bus that he drove across the country in his later years, his art, and other artifacts are part of the Route 66 Hall of Fame & Museum. It all serves as an inspiration to travelers on their journey down the road.

Mural City

Pontiac is home to over 20 murals that adorn buildings throughout downtown. These murals depict life in the town, as well as, its strong relationship to Route 66.

If you’re looking for a great spot to take pictures or just admire Pontiac’s mural art, be sure to head down Main Street where you can find some of the most iconic works.

Just behind the Hall of Fame stands the city’s first mural, the Route 66 Shield Mural painted by the local Diaz Sign Art. As you walk around this parking lot you will find other murals.

Daniels Oil Co. was also painted by Diaz Sign Art. This mural depicts a historic Route 66 gas station and features vintage cars, oil pumps, and gas signs. It’s a great spot to take pictures with your vehicle or just admire the art.

Waldmire Memorial was designed by Bob Waldmire and painted by his family after his death.

The Pontiac-Oakland Automobile Museum

In addition to its many murals, Pontiac is home to the Pontiac-Oakland Automobile Museum. It’s a great spot for car enthusiasts who want to learn about the history of cars on Route 66 and specifically about the Pontiac automotive line.

The museum features a variety of vintage Pontiacs, including the original “Wonder Car” – the Pontiac GTO from 1970. There are also exhibits on classic cars and artifacts that tell the story of Route 66 in Illinois.

So if you’re looking to go back in time and explore one of the most iconic highway routes in America, make sure to add Pontiac to your road trip itinerary. You won’t regret it!

Note: Download Pontiac’s Mobile Device Tour to easily find all of the murals and attractions in town. With this app, you’ll be able to find out more about Pontiac’s history as well as get directions to all the iconic Route 66 sites. This is an excellent tool for those wanting to experience the full breadth of Pontiac’s attractions.

Wally’s – Home of the Great American Road Trip

Before you leave Pontiac, be sure to make a stop at Wally’s. I may have a thing for kitschy large-scale convenience stores and Wally’s with its 30,000-square-foot travel center does NOT disappoint. They coined themselves as the “Home of the Great American Road Trip” and offer travelers everything from freshly popped popcorn and fudge to Wally’s branded souvenirs and snacks.

If you’re looking to take a break from driving, grab a soda or milkshake and use their clean restrooms – it’s an excellent spot! As the sun sets, Wally’s lights up with neon signs that make for some great pictures.

Conclusion:
Our 100-mile journey from Chicago to Pontiac on Route 66 has been filled with adventure, exploration, and unforgettable vacation moments. Along the way, we’ve discovered the history, quirkiness, and charm that make this iconic highway a must-see for every travel-loving family.

Whether you are looking for a Chicago day trip or want to embark on an epic road trip down the “Mother Road”, start at the beginning and explore the many sites along this historic stretch. I can attest there are some unique attractions, fun things to see, and places to eat along the way.

As you continue your travels, remember that there are countless things to see on Route 66 in Illinois that offer endless opportunities for unique experiences and cultural exploration. So, pack your sense of adventure and hit the open road, because the spirit of Route 66 is waiting to inspire your family for miles to come.

Safe travels!