Skip to Content

Road Trip from Baltimore to Chicago

You’ve always longed to check out the Windy City of Chicago, and now you’re ready to make your dreams come true.

Cloud Gate aka The Bean at Chicago Millennium Park

When road tripping from Baltimore to Chicago, how do you prepare?

A road trip from Baltimore to Chicago will take about 13 hours to complete. The route will take you from Baltimore to West Virginia, Pennsylvania, Ohio, and Indiana before finally reaching Chicago, Illinois.

If you’re ready to hop in the car and take a trip with your family from Baltimore to Chicago, this guide will tell you everything you need to know.

I’ll even recommend the top sights, attractions, and activities along your route to make your trip as exciting as reaching Chicago!

The Best Route from Baltimore to Chicago

As I mentioned, your driving route from Baltimore to Chicago will see you crossing through four other states.

This is a trip where it’s certainly not optional to break your driving up into at least two days.

Given that the time behind the wheel can be rather long, you might even want to drive over three days if time allows.

Without further ado, here is my recommended route from Baltimore to Chicago.

Baltimore to Harpers Ferry

From the beauty of Baltimore, you’ll head westward to West Virginia until you reach a town called Harpers Ferry. It should only take you an hour without traffic.

Harpers Ferry is a historic locale with museums that stretch back to the 19th century. If you’re into wartime history, John Brown’s Fort is here.

You can also see West Virginia, Virginia, and Maryland simultaneously at The Point, which is where the Shenandoah and Potomac Rivers converge.  

Harpers Ferry to Breezewood

After you and your family have had your fill of Harpers Ferry, head north from that town to Breezewood, Pennsylvania.

The drive from Harpers Ferry to Breezewood is about an hour and a half if you don’t hit a lot of traffic, so it’s not terribly extensive.

Breezewood is an unincorporated town in south-central Pennsylvania.

Back in colonial times, this town served as a pathway for British troops, European settlers, and Native Americans.

Breezewood to Pittsburgh

You won’t leave Pennsylvania quite yet as you continue your trip to Chi-Town.

Next, it’s time to drive from Breezewood to Pittsburgh by heading northwest through most of Pennsylvania.

This is a longer part of the trip, as it takes you about two hours to get to Pittsburgh.

As a major western Pennsylvania city, you could easily spend days in Pittsburgh alone. The city has an aquarium, a zoo, children’s museums, and even botanical gardens and parks.

If you wish, you can spend a day in Pittsburgh with an overnight stay. If not, then you can continue your drive from Pennsylvania into Ohio.

Pittsburgh to Youngstown

Although crossing the state lines from Pennsylvania to Ohio might sound time-consuming and arduous, it’s actually neither.

You’ll continue northwest to Youngstown, driving for an hour unless you get stuck in traffic.

As the biggest city in Mahoning County, Youngstown is a bustling city that’s known for its steel production to this day.

The city has many beautiful parks, gardens, nature preserves, and even some museums here and there.

If you didn’t spend the night in Pittsburgh, then I would advise you to find a place to stay in Youngstown and call it a night.

Youngstown to Cleveland

When you wake up the next day feeling all bright-eyed and bushy-tailed, it’s time to continue your family vacation and drive from Youngstown to Cleveland, a much more well-known part of Ohio.

This stretch of your trip lasts for about two hours, so make sure you time your drive after morning rush hour so you don’t face unnecessary congestion. You’ll reach the top of the state border.

Cleveland is in northeastern Ohio with markets, museums, a zoo, and a sports field if you and your family have time to check out a game.

You might want to stay overnight to maximize your time here, and I certainly couldn’t blame you!

Cleveland to Toledo

Are you and the family finally ready to leave Cleveland in the rearview? Your next destination is Toledo, which is officially the last stop in Ohio on your Baltimore to Chicago jaunt.

You’ll drive west along the northern border of Ohio to reach Toledo for about two hours without heavy traffic.

With state parks, a zoo, museums, and the famed Imagination Station, trust me when I say that you could entertain your children for days in this city.

If you’re thinking of making it a three-day drive to Chicago, then I’d say park it in Toledo for the night.

You won’t have much driving to do the next day, so there’s that to look forward to!

Toledo to Middlebury

To continue your trip, keep driving west and you’ll get to Indiana from Ohio.

Your stop is Middlebury, which is a two-hour drive without too much traffic.

This town is only 130 miles from Chicago from the east, so you’re almost there!

In the meantime, you can entertain your kids at an orchard or the Pumpkinvine Nature Trail before you finally arrive in Chi-Town.

Middlebury to Chicago

After another two hours, you’re finally in Illinois, and Chicago at that. Congratulations. You’ve made it!

How Long Does It Take to Reach Chicago from Baltimore?

When you set off for your adventuresome trip from Baltimore to Chicago, how long is the drive going to be overall?

This is a long voyage by car, requiring 13 hours of road time altogether.

That’s why I recommend at least two overnight stays but ideally three overnight stays. Otherwise, you’re going to keep the kids in the car for between six and eight hours a day.

No matter the age of your children, from toddlers to teens, that’s going to be uncomfortable for everyone.

Lodging at a few hotels will suck more money from your vacation budget, but it will be worth it for everyone’s high spirits! 

Can’t-miss activities on the road from Baltimore to Chicago

I recommend breaking up what is still a long trip (especially for very young kids) with activities.

All the cities and towns that you’ll pass from Maryland to Illinois have their own charm and attractions, so they’re worth spending at least an hour or two in.

The following list of activities will help you put together a fun itinerary that’s sure to entertain the kids at every turn!

Breezewood Destinations

Once you reach Pennsylvania from Baltimore, Breezewood will be calling your name. While Harpers Ferry doesn’t have a whole lot to do if you and the kids aren’t into history, Breezewood has plenty.

  1. Slinky Action Zone

In nearby Duncansville, the Slinky Action Zone is a family fun center that includes the biggest Soft Play Area in Central Pennsylvania.

So what can the kids do during a visit to Slinky Action Zone? The much better question is what can’t they do?

They can play at the immersive arcade full of prizes to win, games to play, and VR to experience.

They can hop inside the Soft Play tubes, tunnels, bridges, and slides and have a blast.

The children can also play laser tag or Duckpin bowling!

  1. Castle Halloween Museum

Over in Altoona, which is only an hour from Breezewood, is the Castle Halloween Museum, which is run by an owner who’s obsessed with the October 31st holiday.

The museum shows off all nature of Halloween artifacts that were lovingly curated over the years and are now proudly displayed. It can be Halloween all the time here!

Pittsburgh Destinations

As I alluded to above, you’ll find no shortage of family activities in Pittsburgh. Here are my top recommendations.

  1. Children’s Museum of Pittsburgh

Museums are admittedly not every kid’s cup of tea, but I’m sure your own children won’t mind spending time at an interactive, hands-on museum such as the Children’s Museum of Pittsburgh.

The temporary exhibits here change all the time, giving you and the family a reason to come back.

There is also a slew of permanent exhibits, including an art studio, the Kindness Gallery, a Makeshop to play with real tools, and a garage for spinning, climbing, and exploring.

The museum also has a Waterplay permanent exhibit to learn more about rainfall, a garden, outdoor artwork, and a nursery for quiet exploration.

  1. Pittsburgh Zoo & PPG Aquarium

After cooping the kids up in the car for a while, treat them to an afternoon at the Pittsburgh Zoo & PPG Aquarium.

The animals on display between the aquarium and zoo include more than 600 species. You and the kids can witness 8,000 unique animals and counting!

Wild encounters with animals like giraffes and red pandas are available, but the price for these encounters is separate from zoo admission.

The more people who are engaging in the encounter, the more expensive it is.

  1. Kennywood Park

In nearby West Mifflin is the beloved Kennywood, an amusement park that opened in 1899 and has been in regular operation ever since.

This park is the home of the famous Phantom’s Revenge coaster as well as the Steel Curtain coaster.

Of course, worry not. It’s not all about thrill rides at Kennywood. In the Kiddieland section of the park, you’ll find 12 different rides suited for young children.

  1. Sandcastle Water Park

If you’re passing through Pittsburgh in the summertime, then make a beeline to the Sandcastle Water Park.

The park features a slew of water attractions for kids and adults, from the Mon Tsunami Wave Pool to the Mushroom Pool, Thunder Run, Dragon’s Den, the Blue Tubaluba, and Boardwalk Blasters.

The rides vary from mild to intense, so even if you have teens in your party, I promise you they won’t walk away disappointed.

The recommended age for kids to ride the water rides at Sandcastle is six, and they should be at least 36 inches tall.

After drying off, be sure to check out the multiple shops and gift stands scattered throughout the park.

Fill up everyone’s bellies at a la carte restaurants across the park grounds that serve soft pretzels, ice cream, hot dogs, burgers, waffle fries, corn dogs, chicken tenders, and drinks.

Cleveland Destinations

While Youngstown doesn’t really have a lot of kid-friendly destinations, the opposite is very much true in Cleveland.

This city offers a wealth of museums for children as well as plenty of other attractions that are worth your time!

  1. The Children’s Museum of Cleveland

The Children’s Museum of Cleveland is another hands-on museum experience in case you had to pass on the Children’s Museum of Pittsburgh.

Here, your kids can learn, explore, play, and discover their creativity.

The Adventure City two-story climbing exhibit is sure to burn off that pent-up energy from sitting in the car for hours.

The Wonder Lab teaches science, the theater lets kids perform their own productions, and the Making Miniatures exhibit is all about life on a teeny-tiny scale.

The Playlist exhibit is a can’t-miss for your little rock stars, as kids can use fake instruments and props to express themselves musically.

There’s also an Arts & Parts studio for making all natures of artwork!

  1. Memphis Kiddie Park

Despite the name, the Memphis Kiddie Park is located in Brooklyn, Ohio, not Tennessee.

The Memphis Kiddie Park will only entertain the young’uns, so skip this attraction if you have older kids.

The rides include a merry-go-round, pony carts, boat rides, a small Ferris wheel, a kiddie coaster called the Little Dipper, electric cars, and an electric train.

Don’t miss the mini golfing here!

  1. Lake Metroparks Farmpark

The Lake Metroparks Farmpark in Kirtland was established in 1990. It’s an education center and working farm that spans 235 acres.

Across all that space are farm buildings, gardens, and fields.

Kids can see live farm animals such as goats, alpacas, horses, rabbits, chickens, sheep, pigs, and dairy cows.

They can also play on the playground and witness the farm machinery exhibit or explore the plant science center.

The Lake Metroparks Farmhouse is open on Tuesdays through Sundays from 9 a.m. to 5 p.m.

  1. A Christmas Story House

You and the family watch A Christmas Story every holiday season, right? Most households do!

If so, then while you’re in the Cleveland area, you cannot miss the house in the Tremont neighborhood that was used to film iconic scenes in the movie.

The home is a 19th-century, well-maintained Victorian and is quite the popular attraction in the area.

Toledo Destinations

By the time you get to Toledo, you might feel that itch to continue venturing straight through to Chicago, or at least getting some shut-eye so you can drive more tomorrow.

If you do have the time, even on the way back from Chicago, I’d encourage you to spend some time in Toledo enjoying the following family-friendly activities.

  1. Toledo Zoo & Aquarium

The Toledo Zoo & Aquarium is a great spot to visit if you’ve had to decline your kids’ incessant requests to visit the zoos along your route from Baltimore to Chicago.

The zoo has all nature of invertebrates, amphibians, reptiles, mammals, and birds.

At the aquarium, you and the children can witness many unique aquatic species such as the giant Pacific octopus or the flashlight fish.

  1. Imagination Station

The immersive Imagination Station is a hands-on museum experience that the kids will love. As the name says, this place will foster their sense of imagination!

The best part is that the kids are learning all about science while they’re here, but it doesn’t feel like learning.

  1. Pearson Metropark

Let the kiddos breathe in some much-needed fresh air after the latest long stretch of your drive at the Pearson Metropark.

The park offers sledding and ice skating in the cold months and a playground, fishing, tennis courts, soccer fields, and a baseball diamond in the warmer months.

What to do around Chicago

You’ve finally arrived in Chicago. To continue your family-centric fun, here are some destinations and activities to explore.

Navy Pier

Stretching 3,300 feet, Navy Pier has more attractions than you perhaps ever realized.

Kids and adults can ride the carousel, Centennial Wheel (which goes 200 feet in the air), or the other rides in the area.

Shopping is for more than toys or a souvenir. Navy Pier is also home to IT’SUGAR and Kilwins Chocolate Fudge & Ice Cream.

If your kids still have room in their tummies after satisfying their sweet tooths, you can also treat them to pier food such as cupcakes, authentic Chicago hot dogs, deep dish pizza, or gelato.

Lincoln Park Zoo

If you managed to miss every other zoo in the section prior, that’s okay. You can make it up to the children by spending a day together at the Lincoln Park Zoo.

The zoo houses over 200 original animal species of all sorts. Oh, and did I mention the zoo is free too? That’s right!

Shedd Aquarium

If your children are more into aquatic creatures, Chicago is also the home of Shedd Aquarium.

This aquarium is not free, but you can take the money you would have spent at the zoo and use it for tickets.

Where else in Chicago can you see sharks, sea otters, penguins, turtles, living corals, seahorses, saltwater fish, seadragons, whales, dolphins, jellyfish, octopi, and even birds, amphibians, and reptiles? Be sure to schedule a visit!

Chicago Children’s Museum

The Chicago Children’s Museum is sure to provide fun, education, and entertainment.

The exhibits are divided by age, with exhibits designed for toddlers and babies, children ages four through eight, and children nine and over.

Kids can play in boats (that are never in water, don’t worry), paint and draw at an art studio, or dig for dinosaur “bones” at the Dinosaur Exhibition.

Millennium Park

No trip to Chicago is complete without seeing The Bean, which is also known as Cloud Gate.

The Bean is in Millennium Park. Be sure to take lots of family photos!


Taking a road trip from Baltimore to Chicago can be a fun family bonding experience. You and your loved ones can enjoy many great sights, museums aplenty, theme parks and water parks, and even aquariums and zoos.

I wish you a very enjoyable trip!