Catherine - Savvy Family TravelChicago is one of the best home bases in the country for road trips. Within a single day of driving you can reach national parks, historic cities, beach towns, and even another country.
We’ve collected dozens of epic family road trips from Chicago and take special care in breaking up the drive with kid friendly attractions along the way.
In this guide, I’m sharing our best road trips from Chicago, ranging from quick Midwest escapes to longer drives that are worth the miles.
If you’re looking for more getaways with minimal drive time, don’t miss our guide to the best day trips and weekend trips from Chicago, where we highlight easy escapes for 1-3 day trips.
Road Trips from Chicago
Road Trips from Chicago Under 3 Hours
If you’re craving a change of scenery but don’t want to spend all day in the car, there are plenty of action packed destinations within a few of hours of Chicago.
Two of our favorite quick escapes are Madison, Wisconsin and Dubuque, Iowa.
Madison, Wisconsin
Drive time from Chicago: about 2.5 hours
Madison has an easygoing charm that makes it perfect for a spontaneous weekend trip.
One of the most memorable experiences we’ve had here was taking a beginner log rolling class with Madison Log Rolling. The instructors were fantastic with kids and made the whole experience feel welcoming even for beginners.
The Madison Children’s Museum is full of hands-on exhibits, climbing structures, and craft spaces. In the summer, the rooftop play area has unbeatable views of the capitol building.
If you want to get outside, rent a paddle boat on Lake Mendota or take advantage of Madison’s incredible bike trail network. The UW Arboretum Loop is a particularly scenic ride.
Madison also delivers for foodies. Brunch at Marigold Kitchen near the Capitol is always worth the wait, and grabbing donuts from Greenbush Bakery has become a tradition for us.
You can find many more ideas in our full guide to visiting Madison with kids, where we share everything from Hogwarts at the Epic Campus to the best splash pads and mini golf.
Dubuque, Iowa
Drive time from Chicago: about 3 hours
Dubuque sits along the Mississippi River and feels like a hidden gem of the Midwest.
Families will enjoy the National Mississippi River Museum & Aquarium, where kids can learn about river ecosystems, regional wildlife, and get up close and personal with marine life.
Another unique attraction is the Fenelon Place Elevator, a short but steep funicular ride that takes you to panoramic views.
Dubuque works well as a relaxed weekend escape when you want something different from city life without committing to a long drive. Consider a detour to the Toy Train Barn in Argyle, WI or hike with goats in Galena.
You can also complement Dubuque with more family fun in the Quad Cities. Check out the details, here.
3-5 Hour Road Trips from Chicago
Once you expand your driving radius a bit further, the Midwest opens up with charming towns, unique attractions, and scenic natural landscapes.
Door County, Wisconsin
Drive time from Chicago: about 4 hours
Waterfront villages, orchards, and state parks make Door County feel like a relaxed coastal getaway without leaving the region.
Each town along the peninsula has its own personality. In Fish Creek, we always make time for Wild Tomato’s wood-fired pizza followed by frozen custard from Not Licked Yet. In Sister Bay, our kids love Al Johnson’s where goats graze on the roof.
One of the most beautiful natural spots is Cave Point County Park, where waves crash against limestone cliffs. Grab your kids’ hands a little tighter and admire the view.
We also love spending time in Peninsula State Park, climbing the observation tower or biking through the forest. Bike rentals are easily found in the area.
You’ll find a complete itinerary of towns, attractions, and food stops in our full guide to visiting Door County with kids.
Indianapolis, Indiana
Drive time from Chicago: about 3 hours
The Children’s Museum of Indianapolis is the largest children’s museum in the world, and after visiting we completely understand why people plan entire trips around it. Between dinosaur exhibits, sports courts outside, and hands-on science displays, you could easily spend an entire day or two here.
Cool Creek Park & Nature Center has been a great place for kids to run through the trees and burn energy.
Car enthusiasts can’t miss the opportunity to hit the Indy track and visit the Motor Speedway Museum.
You’ll find all our favorite spots in this Indianapolis guide.
St. Louis, Missouri
Drive time from Chicago: about 4.5–5 hours
St. Louis has become one of our favorite Midwest city trips when we want to explore on a budget. Many of its top attractions are completely free! (Gateway Arch & Museum, Zoo, Science Museum, Forest Park, and Lone Elk Park.)
But part of the fun of this road trip is the journey itself between Chicago and St. Louis.
On our drive from Chicago to St. Louis, we stopped at Starved Rock State Park to hike to LaSalle Canyon. The waterfall at the end of the trail was worth every step—and the kids immediately splashed in the pool at the base. Just be sure to bring a change of clothes in the car.
Another unforgettable stop was the Caterpillar Visitor Center in Peoria. My boys climbed into real construction machines and tried operating excavator simulators. Watching their faces light up while “driving” massive trucks was priceless.
In Springfield, we explored Abraham Lincoln’s historic neighborhood and visited the Lincoln Presidential Library, where we saw his famous stovepipe hat up close.
We also stumbled into Charlie Parker’s Diner, where locals insisted we try a Springfield horseshoe sandwich. A table of police officers even brought my boys toy badges from their car after hearing we were visiting.
You can find all of these stops and more in our Chicago to St. Louis road trip guide.
5-7 Hour Road Trips from Chicago
Duluth, Minnesota
Drive time from Chicago: about 7 hours
Perched on the edge of Lake Superior, one of the most iconic sights is the Aerial Lift Bridge, which raises to allow freighters to pass into the harbor. Watching giant ships pass through the canal is a kid pleaser for sure.
Families also enjoy Canal Park, the Great Lakes Aquarium, and the Children’s Museum of Duluth (ASTC reciprocity).
One of our favorite excursions was driving up the North Shore to visit Gooseberry Falls State Park and Split Rock Lighthouse.
You can check out our complete guide to things to do in Duluth with kids for a full itinerary including the Pizza Train and mountain coaster.
Minneapolis, Minnesota
Drive time from Chicago: about 6 hours
I highly recommend planning your Minneapolis road trip from Chicago around their incredible state fair.
Families often spend a full day exploring the Mall of America, where rides, aquariums, and shops make it a true entertainment complex.
Minnehaha Falls is another must-see. The waterfall plunges into a gorge just minutes from downtown.
There’s so much more to explore, like the Como Zoo, log rolling, and more in our Minneapolis guide for families.
Upper Michigan (The Upper Peninsula)
Drive time from Chicago: about 6–7 hours depending on where you go
Towering cliffs, dense forests, and turquoise Lake Superior waters are the biggest draw to Upper Michigan.
One of the most spectacular places to visit is Pictured Rocks National Lakeshore, where colorful sandstone cliffs rise above the lake. It’s best viewed from the water, so book one of the scenic boat cruises.
If you want to explore the western part of the Peninsula, we recommend Porcupine Mountains State Park and Presque Isle.
Many travelers pair an Upper Peninsula trip with a visit to Mackinac Island, where cars are replaced by bicycles and horse-drawn carriages.
7-10 Hour Road Trips from Chicago
Toronto, Ontario
Drive time from Chicago: about 8 hours
Toronto is vibrant, multicultural, and packed with family attractions. The city skyline is dominated by the CN Tower, where you can step onto a glass floor hundreds of feet above the city.
Kids love visiting Ripley’s Aquarium, while the Royal Ontario Museum (ASTC) offers fascinating exhibits ranging from dinosaurs to global history.
We also enjoyed wandering the Distillery District, a historic neighborhood filled with cobblestone streets, cafés, and art galleries.
Another family favorite is taking a ferry to the Toronto Islands.
You’ll find many more ideas in our Toronto family vacation guide.
Niagara Falls & the Finger Lakes
Drive time from Chicago: about 8–9 hours
Easily combined with Toronto, one of our favorite road trips from Chicago was heading to New York’s Finger Lakes region, with a couple days in Niagara Falls.
Two major highlights of the region were Letchworth State Park and Watkins Glen State Park, where we hiked the gorge trail behind waterfalls and stone bridges are carved into the cliffs.
Letchworth State Park, often called the “Grand Canyon of the East,” has breathtaking waterfalls with sweeping views of the Genesee River gorge.
Our Finger Lakes family vacation guide dives deeper into waterfalls, wineries, and scenic stops across the region.
Apostle Islands, Wisconsin
Drive time from Chicago: ~7–8 hours
If you’re looking for a road trip that feels a little more off-the-grid, the Apostle Islands might surprise you.
We broke up the drive with a stop in Wausau, which is a repeated favorite. Here you can stretch your legs along the Riverlife Park area or hike at Rib Mountain State Park. In early July, they host an incredible Hot Air Balloon festival too.
From there, continue toward Bayfield, the gateway to the Apostle Islands. Once you arrive, everything slows down in the best way.
The highlight is getting out on Lake Superior. Whether you take a boat tour, kayak the sea caves (for older kids), or hop on the ferry to Madeline Island, the scenery feels completely different from anywhere else in the Midwest.
For a full breakdown of things to do in Bayfield and our preferred Apostle Island tour, visit our Bayfield guide.
Gatlinburg & the Great Smoky Mountains
Drive time from Chicago: about 9 hours
Gatlinburg is one of the most popular mountain getaways for Midwestern families, and for good reason.
The gateway town sits right at the entrance to the free Great Smoky Mountains National Park, where scenic drives, wildlife sightings, and waterfalls are everywhere.
We usually stretch the drive out over a couple of days and stop in cities like Indianapolis, Cincinnati, and Lexington along the way.
One of our favorite detours has been Mammoth Cave National Park, where underground cave tours completely wowed the kids.
Once we reach Gatlinburg, we spend time hiking in the national park, exploring the town’s quirky attractions, and popping over to Pigeon Forge for even more family fun. There’s a lot to do in Gatlinburg on a budget too!
You can find the full route and all our favorite stops in our Chicago to Gatlinburg road trip guide.
Kansas City, Missouri
Drive time from Chicago: about 7.5 hours
Kansas City surprised us in the best possible way.
Downtown we explored creative attractions like Rabbit hOle, a whimsical museum celebrating children’s literature, and Kaleidoscope, a free art studio where kids can create crafts from recycled materials.
We also rode the KC Streetcar through downtown, visited the Money Museum at the Federal Reserve Bank, and spent hours at Science City at Union Station.
Outside the city center, the Deanna Rose Children’s Farmstead in Overland Park was a hit with younger kids, while the Kansas City Zoo & Aquarium offered an entire day of exploring wildlife exhibits.
Along the way we discovered quirky local stops like alpaca farms, playgrounds, cider orchards, and small-town markets.
Our Kansas City with kids guide breaks down our full multi-day itinerary across different neighborhoods.
10+ Hour Road Trips from Chicago
Myrtle Beach, South Carolina
Drive time from Chicago: about 13 hours
For families craving sunshine and classic beach town fun, this Myrtle Beach itinerary delivers.
Miles of sandy coastline are lined with resorts, mini golf courses, boardwalk attractions, and seafood restaurants.
Because the drive is long, many families break it into two days with overnight stops along the way. One particular stop we loved was Congaree National Park and we have a full road trip from Chicago to Myrtle Beach outlined here.
Once you arrive, make sure to take day trips to the surrounding areas, like Huntington Beach State Park.
Savannah, Georgia
Drive time from Chicago: ~14–15 hours
Savannah is built around a series of shaded squares, each one filled with oak trees draped in Spanish moss. It’s incredibly walkable and romantic.
Some of our favorite ways to experience Savannah:
- Letting the kids run in Forsyth Park.
- Taking a slow walk along River Street to watch the cargo ships pass by
- Grabbing pralines and ice cream between sightseeing stops
- Visiting nearby Tybee Island for a beach day
- If you have older kids, we highly recommend a ghost tour!
A one day Savannah itinerary is available here.
Florida
Drive time from Chicago: roughly 16–20 hours depending on where you go in Florida.
Some families head for the white sand beaches of the Florida Panhandle, while others set out to Orlando for the theme parks, or all the way to Miami and the Keys for sunshine.
We’ve found that splitting the drive over two to three days makes the trip far more enjoyable, with plenty of interesting stops along the road trip from Chicago to Florida.
Some of our favorites include:
- The Retirement Home for Horses (just across the Florida state line)
- BBQ in Macon, GA
- The Aquarium Restaurant and Science Museum in Nashville
- Rock City Gardens
- Fair Oaks Farms
- The Georgia Aquarium
Hot Springs, Arkansas
Drive time from Chicago: about 10 hours
Our road trip to Hot Springs National Park became one of our favorite multi-state adventures.
The journey itself was packed with fun stops. In Illinois we pulled over at Casey, famous for its oversized roadside attractions, and let the kids run around Jeremy “Boo” Rochman Memorial Park.
Further south we explored Giant City State Park before crossing into Tennessee and spending time in Memphis.
Once in Arkansas, we stopped at the Little Rock Central High School National Historic Site and visited the beautiful Garvan Woodland Gardens before arriving in Hot Springs.
The national park itself is unique—historic bathhouses line the main street, and you can even grab a beer at Superior Bathhouse Brewery, the only brewery inside a U.S. national park.
Nearby adventures included the Mid-America Science Museum, Crater of Diamonds State Park, and crystal mining experiences.
We share the full route and all our favorite stops in our Arkansas road trip itinerary.
Packing Essentials for Road Trips from Chicago
A few things we never leave home without:
- Snacks (lots of them)
- Downloaded maps for areas with poor service
- Audiobooks or podcasts
- Easy to grab spare outfits and shoes for spontaneous hikes or splashy waterfalls
- Small trash bin for the car
- Baby wipes for cleaning hands/faces
Final Thoughts on Road Trips from Chicago
Living near Chicago means you’re within reach of an incredible range of destinations.
Within a day’s drive you can explore:
- Great Lakes coastlines
- national parks
- vibrant cities
- beach towns
- mountains
- even international destinations.
Many of our most memorable family moments have happened somewhere between point A and point B. Sometimes the best adventures are closer than you think.
Catherine – Savvy Family Travel
My favorite pastime is finding fun, interesting experiences to share with family and friends.
I’m a mom of two energetic and curious boys. My tireless husband provides comic relief, is our favorite photographer, and an expert navigator.
I’m a firm believer that travel with kids doesn’t have to be intimidating or expensive. It can be affordable, epic, and, dare I say, even relaxing!
Are you a travel loving parent too? I’d love to meet you, please reach out via Messenger and say “hi!”
Based in: Milwaukee, Wisconsin USA