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Shedd Aquarium
World's Largest Covered Wagon

Family Friendly Illinois Route 66 Road Trip

Family Fun

4 Days 345 Miles


Chicago, Joliet, Wilmington, Pontiac, Atlanta, Lincoln, Springfield, Auburn, Great Rivers and Routes, Litchfield, Staunton, Grafton, Alton

Take a family adventure down Illinois’ iconic Route 66

Route 66 is peppered with kid-friendly activities that the whole family can enjoy. Snap a photo at the official start sign in downtown Chicago. Then head south to check out the Route 66 Shield Mural and an arcade museum. In the summer, take the kids to the drive-in theater in Springfield for a double-feature film. Then finish your trip in Grafton by bringing the family on a SkyTour. Whatever your adventure holds, it will surely be a road trip to remember.

Day 1:


  • A family snaps a selfie at Maggie Daley Park in Chicago.

Illinois Route 66 runs nearly 300 miles throughout the state – and it all starts in Chicago. But before you begin your fun-filled trip down the Mother Road, play for a day (or two) in Chicago. From exploring animals at Lincoln Park Zoo to soaking in the incredible views from the Willis Tower Skydeck or 360 Chicago in 875 North Michigan Avenue, there is no shortage of ways to explore the city. The kids can burn some energy playing outdoors at Maggie Daley Park, and while you’re there, be sure to wander next door to Millennium Park to get your family selfie at Cloud Gate aka “The Bean.” For a change of scenery, the Art Institute of Chicago will teach the kids about some of the most iconic and influential artists (plus admission is free for under 14). Endless family fun awaits at Navy Pier right on Chicago’s beautiful lakefront – take a ride on the Centennial Wheel for soaring skyline views, hop on one of many family-friendly boat excursions, or just grab a sweet treat and let the kids splash around in the fountain. From the Pier, you can hop on a Big Bus tour that will take you to Chicago’s Museum Campus, where you’ll have walking access to the Shedd AquariumAdler Planetarium and the Field Museum

You can’t spend the day in Chicago without some incredible food. If you’re 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 (remember: no ketchup). RJ Grunts in Lincoln Park is a cozy, comfort food spot and also 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. Holiday Inn Chicago Downtown - Wolf Point and Embassy Suites by Hilton Downtown are in the heart of the city and both have an indoor swimming pool for the kiddos to use. InterContinental Chicago is right on Michigan Avenue and is the perfect place to stay for an elevated experience. Radisson Blu Aqua hotel is right near Millennium Park plus has a rooftop pool for a summertime splash.

Day 2:

Chicago, Joliet, Wilmington, Pontiac, Atlanta & Lincoln

  • Route 66 Mural with a Pontiac car in front.

Ready to hit the road? Start at the Begin Route 66 Sign sign at the corner of Adams Street and Michigan Avenue, and before you head out of town, make your first official Route 66 stop: breakfast at Lou Mitchell’s,  a classic Chicago family diner that's been feeding hungry travelers with comfort food since 1923. As you head south, your first stop is a tour at the Old Joliet Prison, especially if you’re a Blues Brothers fan. Continue on your journey with a pit stop in Wilmington to get a photo with the Gemini Giant, a 30-ft landmark statue. 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 stretch your legs and check out the Pontiac Art Cars on display. Just south of Pontiac in Atlanta (yes, Illinois!) 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’ll 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 sitting on the front of the wagon. It’s the perfect way to prepare you for your next stop: Springfield!

Day 3:


  • Statue of Abraham Lincoln and his family in front of the White House

Your amazing family photo ops continue in historic Springfield. The World’s Largest Route 66 Shield is located at Motorheads Bar, Grill and Museum and is a spectacle you have to see in person. If you’re taking your Route 66 adventure in the summertime, make sure to spend some time at Knights Action Park where you can enjoy their water park, mini golf and the Route 66 Drive-In Theater. Make sure to get your history fix with the interactive exhibits at the Abraham Lincoln Presidential Library and Museum. Continue your historic Springfield tour with a photo op at the Old State Capitol. To really put yourself back in time, head to the historic portion of Route 66 just outside of Springfield in Auburn. Get some pictures of the whole family on this brick relic of the past. 

All of that sightseeing will work up an appetite. Cozy Dog Drive In is decorated with Route 66 memorabilia and serves up the best Cozy Dog in town! What’s a Cozy Dog? Imagine a corn dog, but even better. While in Springfield you have to try their famous horseshoe sandwich, an open-faced cheeseburger with the fries on top, at D’arcy’s PintCafe Moxo is the perfect place to grab a cup of coffee or a quick bite on the go. The Mahan Filling Station & Fulgenzie’s Pizza & Pasta is a unique spot that is preserving Route 66 history and serving up great food. 

There are many great places to stay with the kids in Springfield. Rest up at the Hampton Inn & Suites, the Residence Inn or the President Abraham Lincoln Doubletree. They are all amazing places to recharge for another day of fun on Route 66.

Day 4:

Great Rivers and Routes—Litchfield, Staunton, Grafton & Alton

  • Sunset at the Sky Tour Gondola.

Continue your Route 66 adventure in Great Rivers Country. Stop at Henry’s Rabbit Ranch for all sorts of on-site rabbits (including real ones). The Pink Elephant Antique Mall is full of vintage items that you can spend the whole day exploring and shopping, and of course there is a big pink elephant out front for that family photo. Also located at the Antique Mall is the Twistee Treat Diner. Grab an ice cream cone or a cheeseburger to refuel after your shopping experience. Head to the Old Chain of Rocks Bridge, which crosses a scenic stretch of the Mississippi River and connects Illinois with Missouri. If the kiddos need to cool off in the summertime, Raging Rivers Waterpark is the perfect place to splash around. For the best views of the Mississippi River and the bluffs in Grafton, you must take a gondola ride at Aerie’s Resort and Grafton SkyTours. Take a ride at sunset and marvel in the beauty. 

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 and a great motto: “Where you eat dessert first!” Post Commons is the perfect place for a coffee pick-me-up while on the go. 

End your stay at the Best Western or the Doubletree Hotel for ultimate family relaxation time.

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