Your Family Will Love These 30 Road Trips Near Chicago
- Updated: 04/03/2024
- Janice
Chicago and US Midwest families, we feel you. Airplane tickets are pricier than ever. Though, your need for a getaway has never been greater.
You want to get out of town with minimal effort and do not want to spend a small fortune to do it.
To help, I share my favorite short to medium-distance driving destinations and those recommended by regional experts—other travel bloggers and planners passionate about places in the Midwest.
Together, we came up with this list of the 30 best road trip destinations for the summer and the fall, from big cities to small charming towns to blow-you-away natural wonders, all within a five-hour drive of Chicago.
Table Of Contents
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Wisconsin: Top Road Trips Within 5 Hours of Chicago
Welcome to Wisconsin, or the “Dairyland State,” loved by visitors for its rich dairy heritage, delicious cheeses, and beautiful landscapes, including miles upon miles of lakeshore coastline.
Check out these six Wisconsin destinations shared in more detail below.
Also, consider adding Green Bay (a 4-hour drive) and the lake-perfect Northwoods towns of Manitowish Waters and Boulder Junction (a 5.5-hour drive) to your driving trip wishlists.
Madison, Wisconsin
Approximate drive time from Chicago: 2.5 to 3 hours
Recommended by: Rebecca Gade Sawicki of VeggiesAbroad.com
At just two and a half hours from Chicago, Madison is the perfect destination for a quick day trip or a weekend away. This sustainability-focused college town offers families tons of outdoor activities, diverse dining, and art and culture.
If you’re a family that loves the outdoors, visiting Madison during the summer is best. This is the prime time to enjoy the city’s prized lake life (five lakes surround it) and over 200 miles of paved bike trails. Madisonians love to bike (even in the winter), which is one of the best ways to see the city.
Another great activity to see Madison’s unique and eco-friendly side is to explore the independent boutiques that line Willy Street. You’ll find plenty of vintage shops, locally created art, zero-waste products, and clothing that’s been ethically produced and sourced.
While you’re in the area, don’t miss an iconic Madison treat, Nutkrack — this sweet and salty snack was actually created by accident! And, around the corner from Nutkrack is Madison’s oldest vegetarian restaurant, Green Owl Café — don’t miss their loaded vegan cheese fries.
When deciding where to stay in the city, the best place is downtown. This will put you within easy walking distance of many shops, restaurants, and events.
The Hyatt Madison/Downtown offers spacious rooms and suites, perfect for families, along with continental breakfast, and has multiple sustainability initiatives to reduce its and its guest’s carbon footprint. Or search for more Madison lodging options here.
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Milwaukee, Wisconsin
Approximate drive time from Chicago: 1.5 hours
Recommended by: Lisa of WavesandCobblestones.com
Milwaukee, Wisconsin, is the perfect city to visit on a family road trip from Chicago. Milwaukee is an easy 1.5-hour drive from Chicago, located to the north along the banks of Lake Michigan.
There are plenty of great things to do in Milwaukee to keep your family entertained! Rent kayaks and paddle along the Milwaukee Riverfront for some fresh air and exercise. Or show some team spirit and take the family to a ball game and watch the Brewers play baseball at the American Family Field or the Bucks on the basketball court at the Fiserv Forum.
There are many fun museums to visit in Milwaukee with your family, such as the Milwaukee Art Museum, a top-notch fine arts museum, where admission is free for children 12 years and younger. Or Discovery World, Milwaukee’s science museum, and Reiman Aquarium. Or the National Bobblehead Hall of Fame and Museum—a one-of-a-kind museum with over 10,000 bobbleheads from across the globe!
Stay at the Plaza Hotel, centrally located in Milwaukee’s historic Lower East Side, with suites that include a pull-out sofa and accommodate up to four people. The Plaza rooms have full kitchens, and with a large grocery store just a block away, you can save money on meals and snacks during your stay.
Or search for more Milwaukee lodging options here.
Sheboygan, Wisconsin
Approximate drive time from Chicago: 2.5 hours
Recommended by: Theresa Goodrich of TheLocalTourist.com
Sheboygan, Wisconsin, is a surprising destination only two and a half hours away from Chicago and a great road trip for families because of the variety of things to do. Begin your visit at the Visit Sheboygan Visitors Center and see Science on a Sphere, a suspended globe that acts as a projector screen displaying programs provided by the National Oceanic and Atmospheric Administration. You can also get tips for places to visit and pick up brochures and souvenirs.
One of the best things to do in Sheboygan for families is Bookworm Gardens. This whimsical garden is a haven for book lovers and children alike, where literature comes to life through vibrant displays and interactive exhibits. Another must-stop for families is the Above and Beyond Children’s Museum. You can’t miss it—there is a ship’s hull sticking out of the building!
While downtown, stroll 8th Street for delicious pizza at Il Ritrovo, and don’t miss the Victorian Chocolate Shoppe. Since Sheboygan is on the shores of Lake Michigan, it is also a great summer vacation spot, with sandy beaches and lakefront parks.
Make Blue Harbor Resort your base camp. With its own waterpark, an arcade, mini-golf, a beach, and outdoor games—the kids will love staying at this resort. Or search for more Sheboygan lodging options here.
Door County, Wisconsin
Approximate drive time from Chicago: 4 to 5 hours
Recommended by: Janice Moskoff of GatherandGoTravel.com
This Wisconsin peninsula just north of Green Bay, surrounded by Lake Michigan, boasts beautiful beaches, scenic hiking trails, and family-friendly activities that will keep everyone pleased for days.
We visited Door County in the fall, and it was gorgeous. The leaves had not quite fully changed, though we took full advantage of the pretty outdoors to bike and hike at several of the peninsula’s five state parks.
We even visited Cave Point County Park, one of the Door’s nearly 20 county parks, and were treated to an easy-to-access spectacular scene of Lake Michigan waves crashing against a stunning rocky coastline on a windy day. The beauty of this experience blew us away. Expect the Door to do the same to you.
In the summer, the Door truly shines. Families flock here for the beaches, events, and the abundance of outdoor activities.
With over 300 miles of shoreline, you can swim, kayak, and fish in the crystal-clear waters of Lake Michigan, especially gorgeous on a sunny day. Plus, the towns dotting the peninsula are charming, full of shops, galleries, and many restaurants.
Visit or stay on the west or bayside of the peninsula, where you can catch sunsets in towns like Fish Creek or Sister Bay. Or opt for the eastside—where we stayed—and catch the sunrises in or around Bailey’s Harbor. Top family-friendly resorts include Newport Resort, Ephraim Shores Resort, and Scandinavian Lodge. Though, know that the Door books early. So, if you plan your trip last minute, grab the best lodging you can get from Sturgeon Bay or further north and use it as a base to drive around and explore the Door.
Search all family-friendly Door County lodging options on VRBO or Booking.com.
Wisconsin Dells, Wisconsin
Approx drive time from Chicago: 3 hours
Recommended by: Hannah & Adam Lukaszewicz of GettingStamped.com
The Wisconsin Dells is the ideal road trip destination from Chicago as it is known as the Waterpark Capital of the World.The driving distance from Chicago to Wisconsin Dells is just under three hours, making it the perfect length for a weekend getaway. Kids love to splash and play in the water, so why not visit multiple waterparks in one road trip?
The Wisconsin Dells is home to the first-ever indoor waterpark and currently has the largest concentration of waterparks in the world. No matter if you are visiting in the summer or the winter, you will find an amazing waterpark for your family to visit and enjoy, as the area is home to 12 different indoor water parks and over 20 water parks in total.
The best place to stay in Wisconsin Dells is one of the Waterpark Hotels. Our favorite waterpark hotel is Great Wolf Lodge as not only does it have a fantastic waterpark with a 6000 ft outdoor pool, 1000 gallon tipping bucket, a wave pool with three-foot-tall waves, a toddler pool, and a variety of slides for kids of all ages.
The Great Wolf Lodge has unique themed rooms and fun activities, including magi-quest, live shows, and an arcade, making it a kid paradise!
Lake Geneva, Wisconsin
Approximate drive time from Chicago: 2 hours
Recommended by: Diana of TravelsinPoland.com
With an approximate driving time of 2 hours, Lake Geneva is a short drive from Chicago and one of the best cities to visit in Wisconsin. The small-town atmosphere combined with a variety of activities make it a perfect choice for families with children of all ages.
Families can enjoy a day on the water, renting boats, kayaks, or paddle boards, or opt for a scenic boat tour around the lake. Or walk along a portion of the Lake Geneva Shore Path, a 21-mile trail that offers stunning views of grand estates and natural beauty. Spending time on the lake is the best way to experience the area, particularly during warmer months. Shopping in downtown Lake Geneva can keep families occupied for hours. The shops along the main roads have unique items such as art and handcrafted goods. There are also mom-and-pop cafes, ice cream, and candy shops in town.
For accommodation, The Abbey Resort, located in the heart of town, offers a great choice. It is a full-service family-friendly resort offering spacious rooms, indoor and outdoor pools, a game room for the kids, and a full-service spa for the adults. Or search for more Lake Geneva lodging options here.
Michigan & Ontario: Top Road Trips Within 5 Hours of Chicago
Experience the best of the Mitten State, a northern gem and a truly ideal destination for vacationing families. The Michigan coastlines—particularly to the west, with sandy beaches, spectacular sunsets, and towering dunes—will wow you with their beauty. Plus, the vibrant cities and small towns in Michigan will offer enough activities and culinary delights to keep you busy and satisfied for days.
Check out these four Michigan & Ontario destinations shared in more detail below.
- Saugatuck, MI
- Ann Arbor, MI
- Detroit, MI, into Ontario, Canada (a loop driving trip)
- Traverse City, MI (with a day trip to Sleeping Bear Dunes National Lakeshore)
To expand your options—consider adding these Michigan Southwest coastal towns to your road-trip-and-relax lists, like New Buffalo, St. Joseph/Benton Harbor, South Haven, Holland, and Grand Haven. Or spend time exploring more urban centers like Detroit or Grand Rapids.
Saugatuck, Michigan
Approximate drive time from Chicago: 3 hours
Recommended by: Janice Moskoff of GatherandGoTravel.com
We love Saugatuck. We have visited for weekend trips several times in the fall and keep returning for more. What draws us? The unbelievably beautiful beaches and dunes, the quaint downtown area filled with art galleries and boutiques, and the concentration of seriously elevated cuisine.
Our favorite beaches are Oval Beach, which consistently ranks as one of the top beaches in the country, and offers soft sand, clear water, and stunning views of Lake Michigan. Additionally, we love the nearby and dog-friendly Saugatuck Dunes State Park, which is perfect for hiking and exploring, with over 1,000 acres of dunes, forests, and beaches.
When not visiting the beaches or getting ice cream, or shopping the galleries on Butler Street, Saugatuck’s main thoroughfare, we spend our time apple picking (in the fall), boating on the Kalamazoo River, or dining at one of the truly fantastic eateries in and around town. I share more things we love to do in Fall Trip: 10 Wonderful Family Things to Do in Saugatuck, MI“
Visiting families also love going on Saugatuck Dune Rides. This thrilling ride takes you on a tour of the dunes, with steep climbs and drops, which the kids will love. And bonus! The knowledgeable guides will share the history and ecology of the area, making it both fun and educational.
For meals, you cannot go wrong nearly anywhere you choose to eat, but our favorites include The Southerner, where the biscuits alone are worth repeat visits, Pennyroyal Cafe & Provisions, and a short 15-minute drive to enjoy drinks and snacks at Virtue Cider.
Booking a stay in Saugatuck can be surprisingly pricey, so I share helpful information on where you can stay in the surrounding areas for less in “Saugatuck, MI: 8 Amazing Areas to Search for Lodging.” Then, and especially because many local inns do not allow children as guests, I detail my top choices for family lodging in “Roundup of the Best Family-Friendly Places to Stay in Saugatuck.”
Ann Arbor, Michigan
Approximate drive time from Chicago: 4 hours
Recommended by: Rebecca Gade Sawicki of VeggiesAbroad.com
Whether you’re a University of Michigan sports enthusiast or just looking for a hip town surrounded by gorgeous natural beauty, Ann Arbor is the ideal Michigan town to visit! From Chicago, the trip via car or train (Amtrak offers service from Chicago’s Union Station to Ann Arbor) is just under four hours, making it a perfect road trip for a few days away!
Ann Arbor is well known for its thriving arts and culture scene. Year-round, it hosts a variety of art, music, and film festivals, including one of the largest outdoor art fairs in the nation, The Ann Arbor Art Fair. The Art Fair takes over Ann Arbor every July and spans 30 city blocks with over 1,000 artists! You’ll also find food and music throughout the fair.
For families who enjoy outdoor activities, you’re in luck! Ann Arbor is surrounded by natural beauty, with parks, nature reserves, and the Huron River flowing through it. Head to the Argo Livery during the summer and rent a canoe, kayak, or stand-up paddle board. You can go out on your own, or Argo offers multiple group river trips that range in time and distance from just under 4 miles and 1.5 hours to almost 6 miles and 2.5 hours.
When it comes to dining, you’re in for a treat — the city is well-known for its eclectic mix of cafes and restaurants. From the famous and funky sandwiches at Zingerman’s Delicatessen to the veggie eats at Ann Arbor’s best vegan restaurant, Detroit Street Filling Station.
When choosing a place to stay, it’s best to stay right in the heart of the city (especially if it’s your first visit). Two terrific family options include the Residence Inn by Marriott Ann Arbor Downtown and The Graduate Ann Arbor. Or search for more Ann Arbor lodging options here.
Detroit to Southwestern Ontario Loop Trip (a 5 Day, 4 Night Itinerary)
Approximate drive time from Chicago to Detroit: 4.5 hours
Recommended by: Erie Conners of EverywhereOntario.com
For a unique road trip that takes you into another country, consider making the trip from Chicago to Southwestern Ontario, Canada. This southernmost region of Canada is filled with quaint small towns, sandy beaches, an abundance of fruit farms and wineries, and incredible historic sites that tell important stories from the Underground Railroad that delivered many slaves to freedom in the 1800s.
From Chicago, you’ll drive 4 hours to the Detroit-Windsor border. In Detroit, you’ll cross the Ambassador Bridge or take the Detroit-Windsor Tunnel to get into Canada.
Depending on how long you’ll be staying in Canada, here are the sites I recommend according to a path that takes you from the Detroit-Windsor border to the Sarnia-Port Huron border, where you’ll loop back to Chicago:
- Windsor: Walk along the scenic Riverfront Trail and Windsor Sculpture Park.
- Optional overnight at Caesar’s Windsor Hotel, or search for other Windsor lodging.
- Point Pelee National Park: Hike, swim, kayak through the marsh, and walk to the southernmost tip of Canada!
- Or, Pelee Island: Take the ferry to Canada’s southernmost landmass, Pelee Island. Visit Pelee Island Winery and bike around the island before taking the ferry home. Overnight in Leamington at a beautiful B&B, or other lodging.
- Overnight in Leamington at a beautiful B&B, or other lodging.
- Visit the fruit farms along Highway 3 (Talbot Trail). Stop at Pardo’s Berrie Farm and pick your own fruits and vegetables during the harvest season.
- Dresden: Tour Josiah Henson’s Museum of African-Canadian History (“Uncle Tom’s Cabin”) to learn about the freedom of slaves from the South.
- Rock Glen Conservation Area: Visit a waterfall and have a picnic lunch.
- Drive to Grand Bend. Overnight at the Colonial Hotel, in Grand Bend, or other stay another nearby property.
- Grand Bend Beach: Visit one of Ontario’s top beaches in the summer months. Lounge on the beach, participate in water sports, or walk along the Grand Bend Strip for boutique shopping.
- Drive to Sarnia via Lakeshore Road and see a stunning sunset along Ontario’s West Coast.
- Sarnia: Walk along the waterfront to see Port Huron from the Canadian side. Overnight at The Insignia Hotel, in Sarnia. Or stay search for other nearby lodging.
- Cross the Bluewater Bridge back to Port Huron and drive 5 hours back to Chicago.
Traverse City, Michigan
Approximate drive time from Chicago: 5 to 5.5 hours
Recommended by: Janice Moskoff of GatherandGoTravel.com
We visited vibrant Traverse City, MI, picturesquely nestled at the southern u-shaped end of Grand Traverse Bay, for five days in the heart of summer with our family dog and loved every minute of our trip.
In addition to enjoying the lakeshore views that front the length of the town and strolling the shops and restaurants of bustling Front Street, our favorite activities were biking along the wooded TART trails—especially the Leelanau Trail, and hiking.
We walked the paths in Grand Traverse Commons Natural Area, located behind the outdoor shopping plaza, making our way to the Hippie Tree, a massive old willow tree at the center of the trail network. Painted in bright colors by locals representing living artwork, the tree is rumored to have a haunted history that we only learned about after our visit.
On another day, we drove out to the Old Mission Point Peninsula to spend the day enjoying the sweeping lake views from the lighthouse, hiking the trails in the adjacent Old Mision Point Park, stopping to buy fresh farmstand cherries, picking blueberries with the kids, and to enjoy a late al fresco lakeside lunch at the Jolly Pumpkin Restaurant & Brewery.
Another highlight was taking a day to visit the Sleeping Dunes National Lakeshore (a 40-minute drive), where we climbed dunes, hiked the Empire Bluff Trail, one of many in the area, and relaxed and picnicked on dog-friendly Esch beach.
In addition to the outdoor activities, which could also include boat trips on Lake Michigan or kayaking on local lakes or rivers, your family will love the varied collection of breweries and wineries with outdoor dining areas ideal for families.When visiting, you can stay at a centrally located and family-friendly hotel, like the Bayshore Resort. Or search for a rental in the area. Find more available Traverse City hotels and lodging here.
Indiana: Top Road Trips Within 5-Hours of Chicago
Hang out in the Hoosier State in one of these two top destinations:
Additionally, consider staying in French Lick, IN, at the French Lick Resort (a 5-hour drive), located in the hills of Indiana’s Hoosier National Forest. It is a classic family-friendly Americana resort offering loads of activities including, golf, biking, hiking, spa treatments, and supervised drop-off kid activities.
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Indiana Dunes National Park, Indiana
Approximate drive time from Chicago: 45 minutes
Recommended by: Caitlin Dismore of TwinFamilyTravels.com
If you are in the Chicago area and looking for a family-friendly trip nearby, definitely consider visiting Indiana Dunes National Park and the surrounding area. Just 45 minutes outside of the city, the park offers a beautiful setting with plenty of beach access points and hiking trails.
In addition to the fabulous activities within the park, the surrounding towns offer a variety of attractions, shopping, and dining to keep the whole family entertained. West Beach is the perfect place for a family outing. It’s the largest beach in Indiana Dunes National Park and is great for swimming, sunbathing, or just relaxing. The Lake Michigan water is clean and clear, and there’s plenty of sand for kids to play with.
Hiking is another popular activity while in the park. Explore Indiana Dune’s biodiversity by hiking along the boardwalks, past historic homes, and even through marsh areas. If you are up for it, complete the 3 Dune Challenge at the nearby Indiana Dunes State Park.
If you are traveling with young children, consider staying at the Country Inn & Suites By Carlson Portage. The hotel has both a standard indoor pool and a shallow pool specifically designed for children, complete with a frog slide. Or search for other lodging options in the nearby Portage, Indiana area.
Indianapolis, Indiana
Approximate drive time from Chicago: 3 to 3.5 hours
Recommended by: Janice Moskoff of GatherandGoTravel.com
This lively Midwestern city offers a wide range of activities and attractions ideal for families. From world-class museums to racetracks, expect a visit to Indy will be a memory-making trip your kids will love.
Top spots include the Indianapolis Children’s Museum, which has 472,900 square feet and five halls of exhibit space, making it the largest children’s museum in the world! While there, kids can explore science, history, and art exhibits. Or they can ride a carousel, board a train, or climb a giant treehouse.
Prefer outdoor activities? Be sure to visit the Indianapolis Zoo and White River Gardens, where the kids can roam, see amazing things, and do fun activities. In addition to seeing tigers, dolphins, and orangutans, the kids can visit the petting zoo, ride trains, join for animal feedings, or watch cheetah racing.
For families who love cars and racing, include a visit to the Indianapolis Motor Speedway. Known as the “Racing Capital of the World,” the speedway is home to the famous Indianapolis 500 race and offers tours of the track and museum. When in the area, stop for burgers and root beers at the Mug ‘n Bun, a nearby vintage drive-in.
On where to stay, consider booking a room at the five-star Conrad Indianapolis tops the list with its spacious rooms and prime downtown location. Prefer something less splurgy?The more budget-friendly Homewood Suites by Hilton Downtown Indianapolis, with a complimentary breakfast, makes for an excellent alternative. Or search for other lodging options in the Indy area here.
Illinois: Top Road Trips Within 5-Hours of Chicago
Check out these top locations in the Land of Lincoln:
Also, consider a visit to Galena (a 2.5 to 3-hour drive) with a historic downtown full of shops and restaurants, nearby outdoor activities like walking and biking along the Galena River, and lots of family-friendly lodging, some with pools.
Starved Rock State Park, Illinois
Approximate drive time from Chicago: 1.5 hours
Recommended by: Alyssa of AnAppleaPlane.com
Only 1.5 hours by car outside the bustling city of Chicago, Starved Rock State Park transports visitors into another world. Dramatic canyons and cascading waterfalls are not the first things you picture when you think of the Midwest!
If you do not plan to drive your own car, renting one will be most effective for your time and budget. Or, you can get to the area by taking a train from Chicago’s Union Station to Mendota Amtrak Station and hailing a 30-minute cab to the park. A huge draw to Starved Rock is its easy-to-access features. Many of Starved Rock’s most famous waterfalls provide drive-up parking lots, so the walk to the waterfall is only a couple of minutes.
Alternatively, consider parking at the main visitor center lot and hiking to your waterfalls of choice. Waterfalls at Starved Rock flow after rainfall or snow melt, so be mindful that these will not be here year-round. The longest-lasting waterfalls are at St. Louis Canyon and La Salle Canyon.
Other top features of the park include hiking, boat tours, and camping. And perhaps the park’s biggest draw—the entrance is free!
Consider staying in the highly-rated Starved Rock Lodge for either cabin or hotel room options. Or search for other nearby family-friendly lodging options here.
Shawnee National Forest, Illinois
Approximate drive time from Chicago: 5 hours
Recommended by: Melissa of HelloWanderlustFamily.com
Located in southern Illinois, Shawnee National Forest is about a 5-hour drive from Chicago, making it an easy and accessible destination for families.
One of the best things about Shawnee National Forest is its variety of activities, such as hiking, fishing, ziplining, or just relaxing in nature—it offers something for everyone. Two must-see attractions are Cave in Rock and Little Grand Canyon Trail. Cave in Rock is a 55-foot-wide cave formed over thousands of years by the forces of the Ohio River and the wind, and a highlight of Little Grand Canyon Trail is you get to hike in and around a series of waterfalls that cascade down the rocky cliffs.
When looking for a place to stay, consider the location of your planned activities. Shawnee National Forest is huge, with some attractions only 15 minutes away, while others may take an hour to reach. Because of this, choose accommodation closer to the area where most of your activities will be.
One excellent lodging option for families is Home2 Suites in Carbondale, which not only provides larger room sizes and access to a pool but is in a city that offers plenty of amenities. Or search for more Carbondale lodging options here. Alternatively, for a more unique and memorable experience, consider staying at the Timber Ridge Outpost & Cabins, which offers cozy treehouses perfect for families seeking a one-of-a-kind stay.
Gurnee, Illinois
Approximate drive time from Chicago: 45 minutes to 1 hour
Recommended by: Lisa of PlanningAway.com
If you are looking for a fun short road trip from Chicago, Gurnee Illinois is just the place! There are lots of fun things to do in Gurnee, Illinois! Gurnee is about 45 minutes north of the city. Home to Six Flags Great America and Great Wolf Lodge, it is the perfect place to spend a fun weekend.
Six Flags Great America is the highlight of a trip to Gurnee. There are over 30 roller coasters and rides to explore. There is also a water park inside Six Flags called Hurricane Harbor. Six Flags has great shows and entertainment options for all ages.
To relax after a fun day at Six Flags, stay nearby at Great Wolf Lodge, where you can enjoy many activities, including an indoor water park, Magiquest game, rock climbing, ropes course, arcade, bowling, and mini golf. Kids will also love character meet and greets, dance parties, and many other fun activities by Great Wolf Lodge, and included in your stay. The lodge is perfect for kids under the age of 12.
There are some places to eat inside Great Wolf Lodge, but if you want to really experience Gurnee, you will want to venture out and try some local favorites. Kaiser Pizza is delicious, and Oberweis Ice Cream is a must. Gurnee Mills shopping and outlet mall is a good stop for families too. Shop at the Bass Pro, eat at the Rainforest Cafe, and enjoy many more fun shopping options. If you do not want to stay overnight—Gurnee also makes for a great day trip from Chicago.
Missouri: Top Road Trips Within 5-Hours of Chicago
Saint Louis, Missouri
Approximate drive time from Chicago: 4 hours 30 minutes
Recommended by: Lynli Roman of Wanderbig.com
With less than five hours between cities, Saint Louis is a family getaway that feels far away but is easy to drive from Chicago in a half-day! Book a room at the railroad depot turned hotel, Union Station, and spend your time exploring the many family-focused activities that Saint Louis offers.
First, take your family to explore the City Museum. Described as “weirdly wonderful,” the City Museum is the crown jewel of family-friendly fun in St Louis. Housed in an old shoe factory, the City Museum boasts a huge network of slides, tunnels, and caves for all ages. All ages love the rooftop, where you can ride the Ferris wheel or climb a giant praying mantis for perfect views of the St Louis skyline.
Next, wander through Soulard Farmers Market and taste your way through the city. The Soulard Farmers Market is one of the oldest markets in the United States, with roots dating back to 1779! Most alive during the weekends, you’ll find 147 stalls filled with unique vendors selling everything from local Missouri produce to handmade gifts. Nearby grounds include a playground and plenty of space for an impromptu picnic with your market spoils.
No family road trip to St Louis is complete without a trip to Forest Park—one of the nation’s largest and most-visited urban parks. The park is home to the Saint Louis Art Museum, the Saint Louis Science Center, the Missouri History Museum, an outdoor theater, and the Saint Louis Zoo. Entrance fees vary, but many amenities, including general admission to the zoo, are free!
Want to see more St. Louis lodging options? Search for other family-friendly accommodation options here.
Ohio: Top Road Trips Within 5-Hours of Chicago
From city trips to world-class amusement parks to under-the-radar natural gems, Ohio regularly delights visitors, and especially families, with all it offers as a vacation destination.
Four Buckeye State destinations to consider for your next road trip include:
Cincinnati, Ohio
Approximate drive time from Chicago: 4.5 to 4.75 hours
Recommended by: Linda of MidwestExplored.com
If you’re looking for one of the best family road trips near Chicago—you can’t beat Cincinnati, Ohio. After all, this underrated city is located just four and a half hours, or 297 miles, away from Chicago and is a well-priced, family-friendly destination brimming over with fun Cincinnati things to do that everyone will love.
So, start your visit with a trip to The Cincinnati Art Museum, founded in 1881, and in the Eden Park area. Not only is the museum free to visit, but there are over 67,000 works that cover 6,000 years, ensuring there is something for everyone at this incredible institution.
Next, grab a picnic lunch and explore Ault Park, which spans an impressive 220 acres of land and is the city’s fourth-largest park, and features a wealth of picnic areas, playgrounds, and walking trails that will help keep energetic kids busy. Finally, learn more about the Underground Railroad at the National Underground Railroad Freedom Center before taking in the electric hue of the cool signs on display at the American Sign Museum.
Then, when you’re ready to call it a day, return to your room at the Hyatt Regency Cincinnati, where you can take advantage of their family-friendly suites, indoor pool and catch up on laundry at their on-site facility. Or search for more Cincinnati lodging options here.
Cleveland, Ohio
Approximate drive time from Chicago: 5 to 5.5 hours
Recommended by: Janice Moskoff of GatherandGoTravel.com
A visit to Cleveland truly offers the best of all worlds—thrills at nearby Cedar Point Amusement Park (1-hour drive), cultural chills, and hills made for hiking at Cuyahoga Valley National Park (30-minute drive).
Stay in town at a place like centrally located and highly-rated Roost Cleveland, which offers fully furnished apartments with hotel-like perks, and use it as a base to explore the area.
The city, on the shores of Lake Erie, is home to the Rock and Roll Hall of Fame, the Cleveland Museum of Art, and the Cleveland Orchestra—great destinations and cultural institutions for families to experience and explore. And when your crew gets hungry, head to the historic West Side Market to grab a bite from local food vendors and souvenir shop for artisanal products.
For families with outdoor enthusiasts, pair a visit to Cleveland with a day trip to Cuyahoga Valley National Park, a 30-minute drive away, where you can hike one of many highly rated wooded or waterfall trails.
Want to see more Cleveland lodging options? Search for other family-friendly accommodation options here.
Cuyahoga Valley National Park, Ohio
Approximate drive time from Chicago: 5 to 5.5 hours
Recommended by: Janice Moskoff of GatherandGoTravel.com
Another must-see destination for families visiting Ohio is Cuyahoga Valley National Park. Located just outside Cleveland (a 30-minute drive), this park offers over 33,000 acres of natural beauty and outdoor activities.
Families can explore the park’s hiking trails, go fishing or kayaking on the Cuyahoga River, or even take a scenic train ride. With its pretty waterfalls, wooded paths, and diverse wildlife, Cuyahoga Valley National Park is a perfect destination for families looking to get outside, get moving, and enjoy the best of what nature and national parks offer.
If you do not plan on staying in Cleveland, consider booking rental lodging in tiny and historic Peninsula Village, a private island of town surrounded by Cuyahoga Valley National Park. Top rental picks in Peninsula, OH, for families include a few three and four-bedroom homes that can sleep up to ten. Search “Peninsula, OH” on VRBO to find them.
Cedar Point Amusement Park, Ohio
Approximate drive time from Chicago: 4.5 hours
Recommended by: Janice Moskoff of GatherandGoTravel.com
Cedar Point Amusement Park, located on a peninsula extending into Lake Erie near Sandusky, Ohio, is surrounded by water and overflowing with family-style fun.
Known as the “Roller Coaster Capital of the World” with over 70 rides, including 18 roller coasters—thrill-seeking families will love it. The park also features a water park, live entertainment, and plenty of family-friendly dining. Take at least two days to enjoy all it has to offer.
Stay on-site at one of the Cedar Point resorts like the beachfront Hotel Breakers, Lighthouse Point offering cottages and campgrounds, Castaway Bay with an indoor water park, or the budget-friendly Cedar Points Express Hotel.
Kentucky: Top Road Trips Within 5-Hours of Chicago
Louisville, KY
Approximate drive time from Chicago: 5 hours
Recommended by: Janice Moskoff of GatherandGoTravel.com
Need a reason to visit Louisville, KY? How about six? Your family will love visiting the Louisville Zoo or strolling along Waterfront Park facing the Ohio River and adjacent to downtown Louisville, stopping to play in playgrounds or cool down in hot summers at the splash park.
While in the area, catch a ride on a riverboat like the Belle of Louisville, which offers several different types of cruises, including historic narrated ones to picnic lunch cruises. Or your whole crew might love the Hometown Music Kids Cruise, designed especially for families.
Kids and parents who love baseball—or love to see how things how are made—will enjoy a visit to the Louisville Slugger Museum & Factory, conveniently located downtown. Your tickets give you access to the museum and a tour of the factory—kids even get a free mini-bat at the end of the tour.
Need an indoor day activity? Explore the Mega Cavern, a former limestone quarry, now an underground adventure park offering ziplining, ropes courses, and a bike park, just a 15-minute drive from downtown and near the Zoo. Or visit the downtown Kentucky Science Center, where your kids can engage with exhibits about the human body and outer space.
For places to stay, The Grady Hotel and Homewood Suites by Hilton Louisville Downtown are great choices. Both hotels are centrally located downtown and highly rated. Or search for more Louisville lodging options here.
Related Reading
For traveling families, check out my related articles below for more trip ideas and tips that will help smooth your travels and get out the door with less hassle.
- Need An Itinerary For A Spring Trip To Europe? Here Are 25 Amazing Ideas
- 31 Warm Winter Break Vacation Ideas Your Family Will Love
- Enjoy the Ride: 12 Tips for Better Family Road Trips
- 15 Tips on How to Raise the Bar on Rental Cars
- Pack Faster & Better With This Universal Printable Packing List
- 25 Expert Packing Tips to Help You Travel Better
- Pre-Trip: A Practical Checklist to Close the House & Pack
Additional Trip Planning Resources
To further help you with travel planning, I share my go-to resources for every trip below.
Google Flights. My first research stop for affordable flights for every trip. Learn why here.
Google Hotels. Use its “Where to stay” button to discover the best neighborhoods to base your visit.
Booking.com. For hotel and rental bookings, I appreciate its flexible cancellation, candid user reviews, discounts, loyalty program, and easy-to-use interface.
Viator, Get Your Guide, & Airbnb Experiences. Quickly find and book highly-rated tours and activities on these sites.
Google Travel Things to Do & Google Maps. Find more things to do in your destination on Google Travel, then record where you want to visit on a custom Google Maps list.
AllTrails. Love to hike? Me too. I religiously use AllTrails to discover hiking and biking trails and download its offline maps to manage my hikes.
Guide Along. 5-star self-guided audio tours that are GPS-compatible for US road trips and national parks. We loved the Glacier National Park tour.
Insure My Trip. I never travel internationally without trip insurance. Learn why here. My preferred place to shop and compare policies is InsureMyTrip.com.
Plus, check out the 15 travel apps I use on trips, my preferred guidebooks, and my free customizable travel itinerary template, downloadable in four file formats.
About the author: Janice Moskoff is a travel writer and blogger who loves hiking, exploring the world, and reading. She writes to inspire travel-loving families, adult friends, and couples on her blog, Gather and Go Travel. Check out her bio, learn how she became a blogger, and discover how to work with her. Sign up for her monthly Discovery Newsletter to get her latest travel recommendations and how-to’s.
Love to travel? Sign up for my monthly Gather & Go Travel Discovery Newsletter and get a free trip budget calculator.
Affiliate Disclosure: Some of the links on this page may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I only recommend products and companies I use. And the income goes to keeping the site community-supported and ads minimal.
Welcome to Gather and Go Travel, a blog inspiring families, adult friends, and couples to explore US and international destinations and to get outdoors. I am Janice, an experienced traveler to over 50 countries and a travel writer, book lover, and blogger. Learn more about me, read our story, and how to work with me.
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