Local road trip adventures for Chicago families

The cost of airfare often persuades families to stay local for vacation, but for Chicagoans, that’s not such a bad problem to have. A short drive can take you to beautiful national parks, local ski resorts and into a number of nearby states and even Canada. But some destinations are much more intriguing than others when you’re on the hunt for things to do with kids during vacation. We rounded up the best road trip routes for families from Chicago, with highlights of where to stop and what sights and activities to include in your itinerary.

5 unmissable family road trips from Chicago

When you’re going on a long drive with kids, you can anticipate the three questions you’ll be asked most frequently: “Can we pull over to go to the bathroom?” “Can I have a snack?” and “Are we there yet?” In light of this, the best way to make the trip more enjoyable is to break up the journey a bit. Instead of trying to reach a destination that’s several hours away on the first day, build a stopover into your itinerary to stretch your legs and distract from the miles you have left. This could be anything from a few hours at a museum in the city to a hike in the woods with an overnight stay in a nearby cabin. After all, the fun of a road trip lies just as much in the journey as the end destination. So, within our recommendations for top family road trips from Chicago, we’ve also included a standout stopover destination.

1. Wisconsin Dells, Wisconsin

Known for: water parks, amusement parks and Dells of the Wisconsin River State Natural Area

Distance from Chicago: 195 miles (3 hours and 15 minutes) 

First stop: Janesville, Wisconsin, located 1 hour and 45 minutes northwest of Chicago and 1.5 hours south of the Wisconsin Dells.

Although there are outdoor activities around the Wisconsin Dells, you’ll likely spend a majority of your time getting thrills at the theme parks here. So, en route, stretch your legs a bit around Janesville, which calls itself “Wisconsin’s Park Place” due to its hundreds of acres of parks and trails. We recommend walking, biking or even rollerblading on the paved portions of the Janesville Trail System, which includes a segment of the statewide Ice Age Trail and also connects to the beautiful 20-acre Rotary Botanical Gardens. 

Wisconsin Dells also has a nickname, which is the “Waterpark Capital of the World,” due to its large concentration of indoor and outdoor waterparks. There’s no better place to cool down in the summer, for both kids and adults (do you ever really outgrow the thrill of a vertical drop water slide?). No matter which park you choose to go to, you’re almost guaranteed that the kids will have a ball splashing around all the attractions. 

And what about the adults? Each park has something to offer, like the lazy river at Noah’s Ark Water Park, the biggest outdoor waterpark in the U.S., or the adults-only swim-up bar over at Wilderness Territory, the country’s largest water park resort. But if you’re looking for an adrenaline rush, Mt. Olympus Water & Theme Park is opening The Rise Of Icarus Experience in the summer of 2024, which will be America’s tallest water slide at 145 feet high!

2. Door County, Wisconsin

Known for: islands, nature parks and beach access

Distance from Chicago: 273 miles (4 hours and 30 minutes)

First stop: Milwaukee, Wisconsin, located 90 minutes north of Chicago and 3 hours south of Door County.

Slip some cultural activities into a mostly outdoor vacation by stopping in Milwaukee on your way to Door County. The city boasts numerous museums for curious kids, like Discovery World Science and Technology Museum, Milwaukee Public Museum (natural history) and the Betty Brinn Children’s Museum (for kids 10 and younger). The little ones should be exhausted after a run through any of these spaces, which means they’ll either get a good night’s sleep at a local hotel or take a rest in the backseat as you finish the last three-hour stretch to Door County.

Once at your destination, you’ll have your pick of scenic attractions. Jagged limestone cliffs rise out of Lake Michigan at Cave Point County Park, best experienced from the water on a kayak. The Niagara Escarpment, filled with rare plants and animals, is a nice hiking destination and especially colorful in the fall. Stargazing is best at Newport State Park, which has a dark-sky designation. With the right conditions, you can see the Milky Way, and on especially dark and cloudless nights, you may be lucky enough to watch the colorful aurora borealis dancing overhead.

3. Traverse City, Michigan

Known for: enormous sand dunes, outdoor recreation, wineries and microbreweries

Distance from Chicago: 320 miles (5 hours)

First stop: Holland, Michigan, located 2 hours and 20 minutes northeast of Chicago and 2 hours and 40 minutes south of Traverse City.

Stopping in Holland will give your family a taste of The Netherlands without having to flex your passports. At Nelis’ Dutch Village, learn how to Klompen dance, watch a wooden shoe-carving demonstration, make your own Dutch Stroopwafel cookie and learn about traditional Dutch villages. Stop at Windmill Island Gardens for a tour of De Zwaan, an authentic Dutch windmill. And if you’re in town from late April to mid-May, go to the Veldheer Tulip Gardens to see multi-colored fields of tulips. 

When you’re ready to “re-enter” America, Traverse City will be your gateway to outdoor exploration. A visit to Sleeping Bear Dunes National Lakeshore is an absolute must. Golden sand dunes that tower as high as 460 feet above Lake Michigan are a natural wonder and offer an incredible view of the shoreline that your family won’t soon forget. Before you reach the dunes, turn left for the entrance to Pierce Stocking Scenic Drive. This worthwhile one- to two-hour detour will take you on a 7.4-mile roadway with 12 stopping points that include a covered bridge and scenic overlooks. 

Back in town, strap on your helmets and start pedaling on the Traverse Area Recreation Trail for a unique way to see the local sights. This network of connected, multi-use trails travels through the city, along the water and into parks and wooded areas. When it’s time to wind down, head out to a local vineyard for wine tasting. You’ll find that the wineries are generally kid-friendly, with lawn space for them to play. Likewise, Traverse City’s microbreweries welcome little ones too, and many have food menus that the whole family will enjoy.

4. Hocking Hills State Park, Ohio 

Known for: caverns, cliffs, waterfalls, zip lining

Distance from Chicago: 411 miles (6 hours and 30 minutes) 

First stop: Indianapolis, located 3 hours southeast of Chicago and 3.5 hours west of Hocking Hills State Park.

One of the recommended driving routes from Chicago to Hocking Hills State Park takes you right through Indianapolis, so it makes sense logistically to stop at this midway point. But perhaps an even better reason to stay for at least a day is to take your little ones to the world’s largest museum made just for them, The Children’s Museum of Indianapolis. This space is home to an incredible variety of treasures and activities. Kids can explore American pop culture and artifacts, go on a journey to ancient Egypt and see a working archaeology lab, learn about astronauts and try on space gear, play sports in an outdoor athletics wonderland and so much more. 

This itinerary is one of the longer family road trips from Chicago, but Hocking Hills State Park is worth the drive. Wooded trail hikes will take your crew to destinations like Rock House, a cave with long sandstone corridors; Cedar Falls, a seasonal waterfall with a 50-foot drop; and Ash Cave, a 700-foot-wide natural horseshoe-shaped cavern with a waterfall, surrounded by towering hemlocks, beech trees and other hardwoods. One of the most popular areas in the park — and most photographed — is Old Man’s Cave, a large recess cave with waterfalls, which has several distinct sections you can explore: Upper Falls, Upper Gorge, Middle Falls, Lower Falls, and Lower Gorge. 

Beyond hiking, there are plenty of other outdoor adventure activities to enjoy, like zip lining, rock climbing, kayaking and rafting trips. There are also some fun and quirky museums in the area, such as the newly reopened Pencil Sharpener Museum and the Ohio Glass Museum and Glass Blowing Studio.

5. Niagara Falls, New York

Known for: awe-inspiring waterfalls, Niagara Gorge and the Maid of the Mist boat tour

Distance from Chicago: 557 miles (8 hours and 45 minutes) 

First stop: Cleveland, Ohio, located 5 hours and 20 minutes east of Chicago and 3 hours and 25 minutes southwest of Niagara Falls.

If you have time to go on a longer family road trip from Chicago, head east to America’s mightiest waterfall. After a long drive of more than five hours, you may want to stop and stay a night or two in Cleveland. The kids will love playing at The Children’s Museum of Cleveland, conducting experiments at the Great Lakes Science Center, learning about women in aviation at the International Women’s Air & Space Museum and making discoveries at the Cleveland Museum of Natural History. By the time you’re done, the little ones will be wiped out for the rest of the drive to Niagara Falls. 

The experience of seeing Niagara Falls in person is one that will stay with your kids forever. You don’t need to bring your passport or cross the border either; you can see all three falls — American Falls, Bridal Veil Falls and Horseshoe Falls — from the U.S. side. Board the Maid of the Mist for a boat tour that will take your family as close as you’ll be able to get to the falls (kids 5 and younger can cruise for free with a paying adult). At night, find a good spot at Prospect Point to view the Niagara Falls State Park fireworks show.

If you stay another day, explore the various hiking trails that run through Niagara Gorge. There are nine to choose from, with many rated for beginners, that range in distance from .7 miles to 5.4 miles. When it’s time to dine, head to Old Falls Street. This three-block cobblestone street has a variety of dining options and seasonal family-friendly activities, including live music.

Get there with Avail

No matter where your family road trip from Chicago takes you, you’ll need a reliable car to get you there. Every trip booked with Avail is protected by Allstate insurance coverage and 24/7 roadside assistance. And you can add a second driver for free. Book today and pick up the perfect vehicle for your trip from any of our dozens of self-service locations throughout Chicago.