Route 66, one of the most iconic routes in the USA, is witness to thousands of families creating core memories on an unforgettable road trip along the highway. Taking kids on a road trip can present many challenges but in Illinois, Route 66 or ‘Mother Road’ as it is dearly called, is the perfect adventure with stops at diverse family-friendly attractions and experiences, local culture, food, and much more. Moreover, with Route 66 gearing up to celebrate its Centennial in 2026, it is undoubtedly an iconic and must-visit road trip destination for all.
Stop 1- Chicago
Commence the road trip in Chicago, a city that has endless experiences to offer everyone. Explore animals at Lincoln Park Zoo, take in the incredible views from the Willis Tower Skydeck or 360 Chicago, visit the family-friendly Maggie Daley Park, and view the Millennium Park and the iconic Cloud Gate aka “The Bean.” Art enthusiasts will have plenty to explore at the Art Institute of Chicago while endless family fun awaits at Navy Pier right on Chicago’s beautiful lakefront featuring the Centennial Wheel with soaring skyline views, boat excursions, and much more. From the Pier, you can hop on a Big Bus tour that will take you to Chicago’s Museum Campus, where you will have walking access to the Shedd Aquarium, Adler Planetarium, and the Field Museum.
You cannot spend the day in Chicago without some incredible food. If you are in the mood for deep-dish pizza, add Gino’s East to your list. Portillo’s will give you the must-have Chicago hot dog experience. RJ Grunts in Lincoln Park is a cozy, comfort food spot and home to the world’s first salad bar. There are plenty of options when it comes to choosing a place to stay in the city including Holiday Inn Chicago Downtown – Wolf Point, Embassy Suites by Hilton Downtown, InterContinental Chicago, and Radisson Blu Aqua hotel.
Stop 2- Joliet, Pontiac, Normal, Atlanta & Lincoln
Start the next day at the Begin Route 66 Sign but before you head out of town, make your first official Route 66 stop for breakfast at Lou Mitchell’s. As you head south, your first stop is a tour of the Old Joliet Prison, especially if you are a Blues Brothers fan. In Pontiac, stop for a photo op at the iconic mural at the Illinois Route 66 Hall of Fame & Museum, and then stroll around the downtown area to check out the Pontiac Art Cars on display. Next up is Normal, visit Ryburn Place, home of the former Sprague’s Super Service, a gas station, cafe, and garage in the golden age of Route 66, and today, a gift shop, Route 66 information centre, known for its Tudor Revival-style architecture. Just south of Normal in Atlanta you will find the Paul Bunyon Statue, one of Route 66’s mythic Muffler Man statues. If you like vintage video games, make sure to go to the Route 66 Arcade Museum, also located in Atlanta. There you will find pinball and other retro games for you and the kids to play. As you continue your journey, make a stop at the World’s Largest Covered Wagon in Lincoln and take a selfie with the 24-foot-tall Abe Lincoln statue.
Stop 3- Springfield
Continue the journey to historic Springfield, home to the Old State Capitol and the World’s Largest Route 66 Shield at Motorheads Bar, Grill and Museum. If you are taking this road trip during summertime, spend some time at Knights Action Park where you can enjoy their water park, mini golf, and the Route 66 Drive-In Theater. Interactive exhibits at the Abraham Lincoln Presidential Library and Museum and the historic portion of Route 66 just outside of Springfield in Auburn are also great spots recommended for history buffs.
Later after a day of exploration, visit Cozy Dog Drive In, decorated with Route 66 memorabilia and serving some of the best Cozy Dogs in town. D’arcy’s Pint’s horseshoe sandwich, an open-faced cheeseburger with fries on top is also worth trying. The Mahan Filling Station & Fulgenzie’s Pizza & Pasta is a unique spot that preserves Route 66 history and serves up great food. There are also many options to stay in Springfield such as the Hampton Inn & Suites, the Residence Inn or the President Abraham Lincoln Doubletree, all family-friendly accommodations.
Stop 4- Great Rivers and Routes—Litchfield, Staunton, Grafton & Alton
Start early the next day and continue your Route 66 adventure in Great Rivers Country. Stop at Henry’s Rabbit Ranch, an emporium of highway and trucking memorabilia also housing a collection of rabbits. The Pink Elephant Antique Mall is full of vintage items that you can spend the whole day exploring and shopping. Also located at the Antique Mall is the Twistee Treat Diner, a quick stop for ice cream and cheeseburger. Head to the Old Chain of Rocks Bridge, which crosses a scenic stretch of the Mississippi River and connects Illinois with Missouri. For the best views of the Mississippi River and the bluffs in Grafton, take a sunset gondola ride at Aerie’s Resort and Grafton SkyTours.
There are many great Route 66-themed places to eat in Great Rivers Country. The Ariston Cafe in Litchfield is a historic Route 66 restaurant and offers a step back in time with delicious food. Doc’s Soda Fountain is another Route 66 joint with great ice cream while Post Commons is the perfect place for a coffee pick-me-up while on the go. End your epic road trip with a cosy stay at the Best Western or the Doubletree Hotel for the ultimate family relaxation time.
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