I recently took this amazing fall trip to Illinois. If this post inspires you to travel to Illinois, make sure to check ahead for up-to-date events, exhibits and opening hours at any attractions.

The Mother Road. The Main Street of America. The historic highway. The supercali-fragilistic-expi-ali-docious route. Okay, so maybe that last one is from Mary Poppins, but you get the idea.

This world-famous highway has been beckoning travelers since the 1920s, and today, it’s easier than ever to pack up and head out on a Route 66 road trip to experience all that this iconic route has to offer.

From the bright lights of Chicago to the sleepy towns dotting the countryside, driving Illinois Route 66 will transport you to a different era as you retrace the steps of countless road-trippers who have come before.

You can go at your own pace, stopping to explore attractions, taking in the scenery, and savoring some of the local flavors along the way. Or you can stick to a stricter schedule and try to hit all of the must-see sights. No matter how you choose to do it, driving Route 66 in Illinois is an unforgettable experience.

The historic highway runs from Chicago to Los Angeles, but for our Route 66 road trip, we chose to focus on the Illinois section of the route. This part of the Mother Road is full of history, natural beauty, and Midwestern hospitality.

We wanted you to experience the best of what Illinois Route 66 road has to offer, so we’ve put together a three-day road trip Route 66 planner that hits all of our favorite spots. This trip can easily be done in one weekend, or you can take your time and stretch it out over a week or more.

It’s time to rev up your engine, put on your favorite driving tunes, and hit the open road! We’re about to take you on the road trip of a lifetime.

(P.S. for tunes, we recommend starting with Nat King Cole’s “(Get Your Kicks on) Route 66” — it’s a classic for a reason!)

Day 1: Chicago

Your Illinois Route 66 road trip begins in the Windy City. This vibrant metropolis is home to world-class museums, award-winning restaurants, and endless activities and attractions. If you’re looking to get a taste of the big city before hitting the open road, there’s no better place to start your journey than Chicago.

Day 1: Morning

Kick things off at Venteux for a late breakfast or early lunch, where you can indulge in delicious French cuisine, including beautiful bakery items, steak frites, whole roasted duck, and oysters that are flown in from the coast daily. (If they have the kouign-amann pastry that day, grab one and any of their seasonal lattes.)

If you don’t fancy French fare, don’t worry — there are plenty of other excellent restaurants to choose from in Chicago. For a truly definitive dining experience, check out Lou Mitchell’s. It’s a classic American diner that’s been open since 1923 and has been serving up breakfast to Route 66 travelers for nearly a century. Be sure to try their famous coffee — you won’t be disappointed!

When you’re all fed and watered, it’s time to explore some of Chicago’s most famous attractions. No visit to the city is complete without the Chicago Architecture Foundation River Cruise, where you can see more than 50 of Chicago’s skyscrapers up close, learn about the city’s fascinating history and architecture, and snap some great photos. It’s just one of many landmarks in Chicago to see! After the cruise was over, we felt like we learned so much about Chicago and viewed the skyline in a new light.

Day 1: Afternoon

After soaking in all that architecture, head to lunch at Billy Goat Tavern. This restaurant was made famous by Saturday Night Live, but it endures because it lets foodies step back in time and experience a slice of Chicago history. The decor hasn’t been updated since the 1950s (with the exception of a private event room and bathroom redo in 2018), and the surly waitstaff adds to the authentic experience. The Double Cheeseburger is the way to go, but you can also order the not-so-secret Obama Burger, which is a Double Cheeseburger with bacon, egg, and grilled onions.

Next on the agenda is a walk through Millennium Park, where you can see Cloud Gate (aka “The Bean”), take in the beautiful gardens and landscapes, and splash in the Crown Fountain.

Afterward, head to the Skydeck , where you can step out onto The Ledge - a glass box that extends four feet outside of the 103rd floor of the Willis Tower, once the tallest building in the world. It’s not for the faint of heart, but the views are incredible!

Day 1: Evening

After working up an appetite with all that sightseeing, it’s time for dinner. If you want to experience some truly world-class cuisine, head to Adalina. This sophisticated bistro takes handmade pasta and wagyu strips to a whole new level while boasting a robust, curated wine list.

Adalina, located in Chicago’s Gold Coast neighborhood, serves innovative and appealing Italian cuisine in a timeless-yet-modern environment. Highlights of the menu include the Charred Octopus, Gnocco Fritto, Ravioli, and Mafaldine.

You’re sure to sleep well after such an action-packed and tasty first day on your Route 66 Illinois road trip!

Day 2: Route 66 Road Trip

After a leisurely start to the day in Chicago, it’s time to hit the open road and begin your journey down Route 66. You’ll be driving through the beautiful countryside today, so be sure to take your time and enjoy the views.

Day 2: Morning

Start your day with breakfast at one of the many fantastic cafes, bakeries, or diners on your Route 66 trip. If you’re in the mood for something sweet, head to the Original Pancake House. Menu highlights include Dutch Baby Pancake and the Apple Pancake. No syrup needed!

When you’re ready to hit the road, grab a photo the sign that marks the start of the Historic Route 66 at East Adams and South Michigan Avenue, then jump in the car and head to your first stop of the day: The Old Joliet Prison. The Joliet Area Historical Museum offers pre-scheduled, guided tours led by knowledgeable tour guides. These walking tours last approximately 90 minutes and cover select areas of the prison campus. The tours are offered from April to October and are the perfect way to learn about the prison’s fascinating history.

Our favorite spots were the prison cafeteria and the rows of jail cells near the end of the tour.

Movie buffs might spot familiar filming locations from Public Enemies (2009) and the opening scene from The Blues Brothers (1980), as the prison has also been featured in several films and television shows.

Day 2: Afternoon

After exploring the Old Joliet Prison, it’s time for lunch. Driving on Illinois Route 66 is the perfect opportunity to try some old-school American diner food, and there’s no better place to do that than at Launching Pad Drive-In Restaurant in Wilmington, home of the Gemini Giant!

The Gemini Giant is a 30-foot-tall statue that was a U.S. Route 66 landmark at the eastern entrance of Wilmington, IL in the 1960s. Now standing outside the Launching Pad, it was one of many giant “Muffler Man” advertising props found throughout America during that decade.

If you want to get a glimpse of small-town America, there’s no better place to do so than here. Plus, it doesn’t hurt that the food is delicious! This institution has been serving up hot dogs, fries, and shakes since 1956, so you can be sure that you’re going to get a mouthwatering taste of the past.

The next stop on your Route 66 trip is Pontiac, Illinois — home of the Route 66 Mural and Hall of Fame Museum. This iconic stop features thousands of artifacts and memorabilia related to Route 66 and is the perfect place to take some fun photos in front of the many murals.

Speaking of murals, our favorites were the large Route 66 Mural, the Soda Fountain Mural, Daniels Oil Mural, and the Visit Pontiac Mural.

Now that you’ve had your fill of murals and history, it’s time to head down to the state capital, Springfield, IL, for the night.

Day 2: Evening

After a day of driving and exploring, it’s time to relax and enjoy some downtime in Springfield. Grab some dinner at Route 66 Motorheads, where you’ll find lots of interesting Route 66 signs, memorabilia, and history, alongside some great food.

We were pleasantly surprised at how many photo opportunities there were at Route 66 Motorheads!

Then, check into your hotel for the night — Inn at 835, Springfield’s only boutique hotel. This unique hotel offers stylish rooms and excellent service.

The hotel was designed by George Helm, a leading architect of his time, and is on the National Register of Historic Places. You’re sure to have a comfortable and enjoyable stay here.

Day 3: Route 66 Road Trip

The final day of your Route 66 road trip is going to be just as action-packed as the first two!

Buckle up and let’s get rolling. — Just one more day until you can say that you’ve driven the entire length of Route 66 in Illinois.

Day 3: Morning

Start your day in Springfield with a hearty breakfast at Custom Cup Coffee. This local favorite is known for its scrumptious coffee and bagels. Grab a delicious breakfast bagel and a pour-over coffee with beans that are roasted in-house, as you get the boost of energy you need to power through your last day of driving Route 66.

When you’re ready to explore, your first stop is going to be the beautiful Illinois State Capitol. This magnificent building is an excellent example of Second Empire-style architecture, and it’s definitely worth a visit.

Make sure to take some time to explore the interior of the Capitol, as well as the surrounding area. The staircase on the upper floors and the legislature room are completely stunning.

Next, head over to the Abraham Lincoln Presidential Library and Museum . This museum is dedicated to the life and legacy of one of America’s most iconic presidents, and it offers a fascinating look at Lincoln’s life, presidency, and assassination.

One could easily spend hours at the museum walking through Lincoln’s life. From his childhood in Kentucky to the days leading up to his assassination at Ford’s Theatre, I guarantee you’ll learn something new about the United States’ 16th president.

Day 3: Afternoon

After exploring the Abraham Lincoln Presidential Library and Museum, it’s time to drive south to Litchfield, IL for lunch at Ariston Cafe — the oldest Route 66 cafe that has stayed consistently open. The ribeye steak and any of their pies are delightful. Eating here felt like being in a time capsule from the 80s.

When you’re done enjoying lunch, continue driving south. As part of this Route 66 planner, we’ve mapped out a few different activities for you to choose from as you make your way to the end of Route 66 in Illinois.

Here are a few of our suggestions:

Henry’s Rabbit Ranch : Did you really think your Route 66 trip would end without seeing some cute lil’ bunny rabbits? Henry’s Rabbit Ranch Station and Visitor’s Center looks like a classic filling station once found all along Route 66, which only adds to the fun, and for good reason. Owner Rich Henry took a trip down Route 66 in 1993, and was disappointed by the lack of visitor centers and souvenirs. Instead of complaining, he simply opened one of his own and has been operating it ever since. You’ll find two types of “rabbits” here — VW Rabbit cars, and yes, cute fluffy bunny rabbits. Henry’s daughter, who adopted two bunnies, didn’t account for what can happen when a boy and girl bunny get together. Multiple generations abounded and Rich now keeps the fluffy gang on the ranch where he has more space than his daughter’s studio apartment affords. Rich has even trained a few of the rabbits to do tricks for visitors. Be sure to hop in and say hello!

Pink Elephant Antique Mall : For 15 years, Pink Elephant Antique Mall has provided Livingston residents with a place to find encapsulating antiques as well as fresh homemade candy and fudge. Decorate your home with unique farmhouse items from their wide selection or take a sweet treat to go. You can grab a lovely photo op at the front and inside the retro cafe, but also make sure to get a soft-serve cone; it’s a must-have!

Chirping Frog Antique Mall : Similar to Livingston’s Pink Elephant, Chirping Frog offers an array of rustic and unique goods. It’s one of the most organized antique stores you will ever visit and includes an impressive inventory of furniture, pottery, glassware, metalwork, textiles, and more. They also offer a wide range of books on topics like local history, Route 66, and the Civil War.

World’s Largest Catsup Bottle : Let’s face it, you can’t have a Route 66 road trip and not stop at the World’s Largest Catsup Bottle. Located in Collinsville, this massive water tower has been a Route 66 staple since 1949 and was even declared a historical landmark in 2002. This is a fun place to take some photos and stretch your legs.

Day 3: Evening

End your day with a bang by visiting Grafton and taking the Grafton SkyTour at Aerie’s Resort. Labeled “the best view in the Midwest,” you’ll surely want to take advantage of this opportunity to see some of the most beautiful scenery Illinois has to offer.

Aerie’s Resort boasts a winery, an aerial adventure course, and a variety of dining options, so you can really make a day (or night) of it. It’s also home to the first alpine coaster in Illinois, which is perfect for any thrill seekers out there.

After a long day of exploring, you’ll probably be pretty hungry. Luckily, Grafton Oyster Bar is just a short walk from Aerie’s Resort and offers some of the freshest seafood around. Of course, we highly recommend the oysters, but you really can’t go wrong with any of their seafood options.

When you’re finally ready to call it a night, you can head back to Aerie’s Resort and crash in one of their cozy rooms. You’ll definitely sleep well after all the excitement of the past few days!

Day 4: Last Day

Start your last day on Route 66 with breakfast at Post Commons in Alton. A former Post Office, it’s one of the most beautiful coffee shops I’ve ever been to with a cavernous interior and loads of stylish design touches. The specialty coffee and baked goods here are simply divine.

Afterward, make sure to check out the life-size Robert Wadlow Statue — the tallest human being in history!

Before ending your road trip in Illinois, stop by the old Chain of Rocks Bridge to see a piece of Route 66 history. Built in 1929, the 30 degree turn halfway across this mile-long bridge over the Mississippi makes it one of the most unique bridges in America. Drivers used the bridge for decades, until the new Chain of Rocks Bridge was built further upstream in 1967.

The old bridge was neglected, and in danger of being torn down more than once. However, in 1999, after a lot of love and restoration by a group called Trailnet, the old Chain of Rocks Bridge reopened to the public as a bikeway. The bridge now connects more than 300 miles of trails on both sides of the Mississippi River along the Route 66 Bikeway.

That’s it for our Illinois Route 66 road trip itinerary. We hope you have a blast exploring all that this historic route has to offer; we know we did! Remember to take plenty of pictures and enjoy the ride!

Hit the Open Road: The Ultimate Route 66 Road Trip Itinerary in Illinois

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