Unlocking the Best Road Trips for Teens in the Midwest: A Family Guide

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As any parent with teenagers knows, road trips for teens require more than the promise of scenic views and hotel pools. It’s about striking a balance between adventure and the allure of the new, with the comfort and safety a family trip implies.

Finding destinations in the Midwest that resonate with teens is a task that combines the art of understanding their interests with the science of logistics. We embark upon several road trips every year, so I’ve got a pretty good idea of what my teens like – and I suspect yours will too.

Here are some of the best road trips the Midwest has to offer to families with teenagers. From the iconic Gateway Arch of St. Louis to the speedways of Indianapolis, the vibrant urban landscapes of Chicago to the natural wonders of Hocking Hills, and the serene beauty of Northern Michigan — I’ve got five terrific ideas for family adventures that teens won’t just enjoy but will remember well into adulthood.

Top 5 Midwest Road Trip Destinations for Teens

Ready to take off on your family road trip? Pick one of these top 5 destinations and be ready for a vacation full of memories.

Chicago skyline

1. Road trip to Chicago, Illinois

A road trip to Chicago is a great choice from anywhere in the Midwest. It’s an easy 3-hour drive from Indianapolis, a longer but still manageable trip from St. Louis or Columbus, Ohio, and a fun journey from pretty much anywhere in Illinois, Michigan, Indiana, Iowa, or Ohio.

stop at Starved Rock State park on your way to Chicago

What to do along the way

Regardless of your starting point, you’ll want to give yourself a few days in Chicago, so plan your trip accordingly. If you are coming through Indianapolis, consider at least a day there. Driving up through Illinois? Stop in Springfield or for a night at Starved Rock State Park – both are FULL of fun adventures.

If your teen hasn’t been to a big city yet, Chicago will be amazing for them. My kids love the hustle and bustle of the city. Living in Indianapolis, we actually get up there regularly and they never get tired of it!

What to do in Chicago Illinois

If this is your first visit to Chicago, something I recommend (and we’ve done just for fun) is to book a Big Bus Tour. It’s meant to be a get-on / get-off method of transportation and you can definitely do that (and should), but get your pass early enough in your trip to use it as a way to get a guided overview of the city. It will help you get your bearings and decide what you want to add to your itinerary.

A few good options for your teens are to visit one or two of the wonderful museums in the city – at least one of them probably caters to their interests. If your kid likes astronomy, check out the Adler Planetarium. Science? The Museum of Science & Industry is a winner (and my daughter’s favorite!). And on and on. A few more thrilling ideas include a visit to the SkyDeck in the Willis Tower or a FAST speedboat cruise in Lake Michigan. Honestly, I could keep going and going – suffice it to say you (and your teens) won’t be bored in Chicago!

💥Pam’s Insider tip: If you are spending a few days in Chicago, consider buying a GoCity Pass – you’ll save a lot of money on the top sites!

Grab a coffee at the Starbucks roastery in Chicago

Where to eat in Chicago

And for teens who like good food? Chicago will deliver. Definitely indulge in Chicago-style deep-dish pizza. You’ll find a deep-dish pizza option in every part of the city, and many locals feel quite passionately about their favorite one. Ask around and I bet you’ll get a variety of answers as to which is the best. As a non-local, I like them all!

Consider Eataly for a fun food court-type atmosphere where you’ll find something delicious for everyone (and can even pick up fun ingredients to take home and make something with later). Finally, if your teens love Starbucks, then you’ll definitely want to take them to the five-story Starbucks Roastery – it’s something to see!

Where to stay in Chicago

We always stay at The Blake when we visit Chicago. I love that it’s a short walk to the riverfront, and convenient to some yummy restaurants. If it’s summer when we stay, we will grab our coffees and walk down to Millenium Park or the Magnificent Mile.

Columbus Ohio skyline

2. Try a road trip from Columbus, Ohio to Hocking Hills

Columbus, Ohio is a fantastic city with lots to do for teens, and it’s a great combination with an outdoorsy trip to Hocking Hills, Ohio.

What to do along the way

Start your trip with a day or two in Columbus. Two fun options for family-friendly events are COSI and the Columbus Zoo. It’s also fun to check out the various neighborhoods in a city like Columbus – my teens enjoy that a lot.

waterfall at Hocking Hills State Park

What to do at Hocking Hills State Park

Hocking Hills State Park offers an adventurous choice for teens eager to explore the wild. The park’s myriad hiking trails, like the popular Old Man’s Cave or the challenging Cantwell Cliffs, offer a thrilling trek through a variety of lush forests, deep gorges, and cascading waterfalls.

If your teen loves photography or has a flair for the dramatic, the park’s awe-inspiring landscapes are perfect for capturing that epic Instagram shot or even dabbling in a bit of amateur nature photography.

Beyond the trails, Hocking Hills ignites the adventurous spirit with its canopy tours, featuring zip-lining experiences. For real daredevils, rock climbing and rappelling are also on the menu, offering both novice and experienced climbers the chance to scale the park’s imposing rock faces.

After a day full of action, the star-gazing events at John Glenn Astronomy Park promise a serene evening under the night sky, where teens can ponder the vastness of the universe or spot a shooting star.

Where to stay when visiting Hocking Hills State Park

There are tons of cool options for places to stay when visiting Hocking Hills State Park. From tiny homes and treehouses to gorgeous resort lodges, you’ll have no problem finding a place that your teens will love.

If you prefer a hotel, most of the chains have locations in nearby Logan, Ohio. For example, this highly-rated MainStay Suites looks fabulous. It’s in a great location and the rooms have kitchenettes to help you save a little money!

Indianapolis skyline

3. Head to Indianapolis, IN from Louisville, KY

As an Indianapolis, Indiana resident, I can guarantee your whole family can have a blast in my city. And if you are taking off from Louisville, KY, it’s an easy two-hour drive with some great stops along the way.

What to do along the way

Although there are plenty of cute small towns just off of I-65 between Louisville and Indianapolis, my top picks would be Columbus, IN, or Nashville, IN. If your teens like architecture, stop in Columbus and participate in one of the interesting architecture tours. More outdoorsy? Then do a little hiking at Brown County State Park in Nashville before arriving in Indianapolis and doing all the “city” stuff.

What to do in Indianapolis, IN

Like other Midwestern cities, Indianapolis is big enough to have plenty to do while being small enough to easily get around. It’s perfect for a road trip because you really do need a car to enjoy it to the max.

A few highlights for the kids include a visit to the Indianapolis Motor Speedway – it’s pretty amazing whether you are a racing fan or not, as well as a trip to the Indianapolis Zoo. If your kids are sports fanatics, they might enjoy checking out the NCAA Hall of Champions and maybe an Indianapolis Colts or Indiana Pacers game. We are definitely a sports city!

💥 Pam’s insider tip: If your kids are foodies, consider a fun food tour in one of our cultural arts districts like Mass Ave or Fountain Square. I did one of these on a recent trip to Ybor City and it was a fantastic activity for my teenage son and me.

Tenderloin sliders at Oasis Diner in Plainfield, IN

Where to eat in Indianapolis

When you find yourself in Indiana, you really ought to enjoy at least one tenderloin sandwich and some sugar cream pie. It doesn’t get any more Hoosier than that. I’d suggest a stop at one of the local breweries for the sandwich (like Upland Brewing in Fountain Square) and just look on any menu for the sugar cream pie – it’s a common dessert in the city. Another delicious tenderloin can be found in nearby Plainfield at the Oasis Diner -so good!

Also, head over to The Garage Food Hall on Mass Ave. It’s a super fun food hall with unique food choices, great drinks, and a fun atmosphere – perfect for families with teenagers.

Where to stay in Indianapolis, IN

If your teens like a bougie stay, then book The Bottleworks Hotel on Mass Ave. It’s stunning and right next to plenty of shops and restaurants perfect for strolling. If you prefer a little more space, consider the Staybridge Suites downtown. With kitchens in the room and free breakfast, it’s an affordable and comfortable option.

Beach at Petoskey State Park

4. Road trip from Ft. Wayne, Indiana to Northern Michigan

We’ve done this road trip dozens of times and it’s always a family favorite. I love visiting Northern Michigan in the winter to ski at Boyne Mountain or in the summer and fall to enjoy Petoskey.

What to do along the way

Starting in Fort Wayne, there are several places we’ll often stop on our way to Northern Michigan. Lansing is always a favorite. If we’ve timed it right, we’ll enjoy picking up some goodies at Horrocks Farm Market. It’s an amazing mix of farm market, deli, pizza place, gelato and so much more. The coffee and candy areas are fabulous and don’t even get me started on the beer and wine section! We always stock up on their Habanero Pickles to enjoy at home.

If it’s summer, sometimes we’ll pull over at Uncle John’s Cider Mill for some cider tasting – it’s a nice way to break up the drive (just make sure if you are enjoying the hard ciders someone else is driving!). The next great stop is Gaylord, Michigan. It’s a cute little town and every few years we stop to see what has changed.

Ski runs at Boyne Mountain

What to do in Northern Michigan

My teens love Northern Michigan. They’ve been visiting since they were babies, and yet we still discover something different on every trip! In the winter of course we are going to ski at Boyne Mountain or Boyne Highlands. There are plenty of other fun things to do in the winter, and most teens really enjoy the ski mountain vibe.

In the summer, the golf courses are lovely. My teenage son always wants to head up for a short golf trip in the summer and then we’ll often bring a carload of boys (him and his friends) for Labor Day where they can play disc golf, go to the waterpark, paintball, and more. Another favorite for teens is the beach at Petoskey State Park – it feels like visiting the ocean – without the salt water. Such a fun spot for teens!

Where to eat in Northern Michigan

There are plenty of fantastic choices if you are staying at Boyne Moutain. The Trophy Room Pizza and Forty-Acres are almost always on our list. But, we also like to venture out to Boyne City and Petoskey – and once in a while Charlevoix. A few favorites include Happy’s Taco Truck at the Back Lot in Petoskey and Cafe Sante in Boyne City.

Where to stay in Northern Michigan

Nine times out of ten we stay at Boyne Mountain when we visit Northern Michigan. I like the resort feel and my kids have stayed there so many times that they know their way around so they get a little more freedom. If we aren’t at Boyne, there are some great choices in Petoskey, such as the Holiday Inn Express or the newer Courtyard by Marriott.

St. Louis Skyline

5. Road trip from Indianapolis, IN to St. Louis, Missouri

My final suggestion for a Midwestern road trip for teens is from Indianapolis, Indiana to St. Louis, Missouri. This easy four-hour trip is one we’ve taken many times through the years and in fact have three long weekends on the books for soccer season this year alone.

standing in front of the World's Largest Mailbox in Casey, Illinois

What to do along the way

We do not make this road trip without a stop in Casey, Illinois. It’s a small town full of big things. Originally we stopped because of a road sign that said we’d see the world’s largest windchime and world’s largest golf tee. Since that trip many years ago the town has added TONS of other big things. A birdcage you can get in? Yep. World’s largest working knitting needles? It’s there. A super-sized mailbox where you can actually send out mail? You’ll find it in Casey. along with many other fun sights to see.

Even better, it’s almost exactly halfway between Indianapolis and St. Louis, so the perfect timing for a stop. Once you hop back into your car, drive just a little bit further and pull over at Blue Springs Cafe for a slice of mile-high pie. Between the pie and Casey, IL you’ll get plenty of fun pictures that your teens will be happy to pose for!

What to do in St. Louis, Missouri

St. Louis is another town I love for teens. The Gateway Arch is amazing and my teens always get a kick out of the ride to the top. We also like to visit the St. Louis Aquarium and Union Station area, and I don’t know a kid of any age who doesn’t love the City Museum.

For kids who love music, take some time to check out the National Blues Museum – it is really well done with plenty of hands-on exhibits and interesting tidbits about the Blues. Sports fans will enjoy a Cardinals game, so if it’s baseball season pick up tickets before your trip.

💥 Pam’s insider tip: If you haven’t been to St. Louis before, consider this affordably priced and highly-rated trolley tour. It’s a great way to get the lay of the land, and you and your teens can decide which attractions you want to go back to during your visit.

Sauces from Sugarfire Smokehouse in St. Louis, Missouri

Where to eat in St. Louis

You’ll definitely want to get some BBQ while you are in St. Louis – the city is known for it. Sugarfire Smokehouse is a good choice, but honestly, you’ll be happy with any of the BBQ spots in the city. We also like to visit the Italian district when we visit and enjoy some homemade pasta and salads at a place like Zia’s on the Hill. Yum! Finally, Fitz’s is a fun choice for teens (or adults) who love really good rootbeer.

Where to stay in St. Louis

For families, I love the Drury Hotels in St. Louis. Either the Drury Plaza at the Arch which is fantastic for visiting the arch, the riverfront, and downtown, or the Drury Inn and Suites at Union Station for visiting that part of town. What I like about both of these is that in addition to great locations, they have a fantastic breakfast as well as a happy hour that is included in the room rate. This can save you a ton of money on eating at restaurants during your visit.

Why the Midwest is Perfect for Road Trips with Teens

As a Midwesterner myself, I truly believe that the Midwest is an ideal setting for family road trips with teens, offering a wide range of activities that cater to diverse interests. Outdoor enthusiasts can revel in activities like kayaking, hiking, and cycling through the region’s various landscapes. City trips are equally rewarding, with plenty of urban centers boasting a mix of arts, culture, and interactive museums that are both fun and educational.

In terms of value, the Midwest stands out for its affordability, especially when compared to destinations on the coasts. This cost-effectiveness means families can enjoy a fuller vacation experience. You can expect to get more out of every dollar spent on attractions, dining, and lodging, allowing for a trip that’s rich in experiences without the financial strain – and with the way that prices are rising, that’s a HUGE win in my book.

Families with teens will find the Midwest particularly appealing because of this blend of engaging activities and economic practicality. It’s a region where the journey itself becomes a canvas for building memories, all without the pressure of excessive spending. This balance of excitement and affordability makes the Midwest an excellent choice for road trips with teens.

a hotel room in the Midwest

Planning Your Road Trip: Things to Consider

Planning a road trip with teens doesn’t have to strain your finances. Start by setting a clear budget that covers all bases—transportation, accommodation, food, and activities. To save, consider traveling off-peak or staying in budget-friendly accommodations. Packing meals for the road and seeking out free or low-cost attractions can also help keep expenses down, ensuring you get the most out of every dollar without compromising on the fun.

When it comes to timing your Midwest road trip, the late spring to early fall window is ideal. During these months, the weather is typically pleasant, making it perfect for both outdoor adventures and city exploration. Avoiding the peak summer season can also mean fewer crowds and potentially lower costs. Additionally, many attractions and outdoor activities are at their best during these seasons, providing the perfect backdrop for your family’s journey.

Involving teens in the planning process is crucial to ensure the trip appeals to their interests. Have them list activities or sights they’re excited about, and incorporate these into your itinerary. This not only ensures that the destinations align with their preferences but also gives them a sense of ownership over the trip. When teens are part of the planning, they’re more likely to be engaged and enthusiastic travelers – at least mine are!

I usually let each of my kids pick one must-do and one must-eat for every road trip we take. This way I know that they are both excited about a few things, and honestly, it’s a little less planning for me. Win-win.

Must-Have Travel Gear for Teens

For a road trip with teens, keeping their tech charged is paramount. Must-have travel gear includes portable battery packs and car chargers to ensure smartphones, tablets, and gaming devices stay powered up during long drives. A sturdy, water-resistant backpack or even a string bag for each teen can serve as a personal carry-all for snacks, water bottles, and those essential gadgets, allowing for organized and accessible travel essentials.

Comfort is key, so packing items like travel pillows and blankets can make the journey more enjoyable for your teen passengers, especially during longer stretches of travel. We always each bring a blanket for the car – and it’s always a variety of these amazing Vera Bradley blankets.

Noise-canceling headphones are also a great investment, giving teens the space to retreat into their music or audiobooks, making the miles fly by. These items not only enhance comfort but also give teens a sense of personal space, even in a packed vehicle.

Skiing with my teenage daughter in the Midwest

Making the Most of Your Trip: Quick Tips

Creating a flexible itinerary is key to a successful road trip with teens. While it’s important to have a plan, be ready to adapt based on mood and interest. Schedule the must-see destinations and book essential accommodations, but leave room for spontaneous detours or unexpected attractions that might catch your family’s interest. This approach keeps the trip exciting and allows for discoveries along the way.

Teenagers value their independence, so it’s beneficial to weave in opportunities for them to explore on their own or enjoy some downtime. Whether it’s allowing them to wander through a museum at their own pace, choose a restaurant for dinner, or simply hang back at the hotel to relax, this alone time can enhance their overall experience.

Respecting their need for space will make the times spent together on the trip even more enjoyable. It took me a while to feel comfortable with this one, but once the kids hit about sixteen, I’d let them go back up to the room while we were at the pool or even sleep in while we grab breakfast and explore a little on our own (depending upon our location and where we were staying of course).

Finally, encourage everyone to capture memories, but go beyond just snapping photos. Providing them with a travel journal can also be a great way for them to note down experiences from their perspective. These tangible memories become priceless keepsakes that tell the story of their journey and the adventures they had along the way.

Map of 5 Road Trip Final Destinations

Conclusion: The Best Midwest Road Trips for Teens

As a Midwesterner myself, I know firsthand the eclectic charm and boundless opportunities our region offers for families embarking on road trips with their teens. These destinations within the Midwest are more than just stops on a map; they are wonderful experiences that cater to the adventurous, the curious, and the independent spirits of teenagers. They blend natural wonders, urban excitement, and educational insights, all within the comfortable reach of a family-focused budget.

These five road trips across the Midwest are curated to hit that sweet spot of teen engagement and family bonding. The variety of activities available ensures that teens with diverse interests find something to rave about, from the adrenaline rush of outdoor adventures to the cool factor of city explorations. These journeys promise to enrich your family album with shared memories and stories to tell for years to come.

Give one (or more) of them a try – I think you’ll be surprised at how much the Midwest has to offer for your teens, and I guarantee you’ll end the trip with plenty of insider family stories and shared experiences!


Get ready for an epic adventure!  Our latest blog post reveals 5 unforgettable Midwest road trips that are perfect for creating precious memories with your teens. From the vibrant streets of Chicago to the stunning landscapes of Northern Michigan, there's something for everyone. Are you excited to hit the road?  #RoadTripGoals #MidwestAdventures
Get ready for an epic adventure!  Our latest blog post reveals 5 unforgettable Midwest road trips that are perfect for creating precious memories with your teens. From the vibrant streets of Chicago to the stunning landscapes of Northern Michigan, there's something for everyone. Are you excited to hit the road?  #RoadTripGoals #MidwestAdventures