Go from one major American city to another. Whether you want to spend time on one of the Great Lakes relaxing and kicking back or desire to explore the big city, our Chicago to New York City road trip will do the trick.
Travel east on a Chicago to New York City road trip for lots of fun, romance and adventure. You’ll go through lakefront communities, metropolitan cities and resort towns on your way to the Big Apple from the Windy City. This journey will take you through six states; you’ll start in Illinois, go through Indiana, Ohio, Pennsylvania and New Jersey, and finally hit New York.
Stops
1. Chicago
2. South Bend, IN
3. Sandusky, OH
4. Cleveland, OH
5. Black Moshannon State Forest
6. New York City
Info at a glance
- A 2-week trip.
- Type of route: Family
- 6 stops along the route
- 834 miles of driving
Highlights
- Indulge in some chocolates at the South Bend Chocolate Factory.
- Visit the Cedar Point Amusement Park to ride some roller coasters or watch a few shows.
- Attend a professional sports game while in Cleveland.
- Catch a glimpse of an elk in Moshannon State Forest.
- See a Broadway show in New York City.
Getting to the start
You’ll travel east on Interstate 80 and I-90 to go from Chicago to New York City. If you fly into Chicago, you’ll arrive at either Chicago O’Hare or Chicago Midway Airport. You can rent a car at either of these airports to get to New York City. Amtrak trains stop at Chicago Union Station, if you want a unique way to arrive in the city. If you’re coming from the surrounding region, you can take I-90, I-80 or I-94 from the east or west, I-94 from the north or I-57 and I-55 from the south, among others.
When to Visit
Both Chicago and New York City can be cold and snowy in the winter months. Because you’ll be driving through Ohio and Pennsylvania, you might also encounter snow if you’re traveling between the months of November and March. For this reason, it is best to take this trip in the late spring, summer or early fall, i.e., April through October. Because you’ll do lots of walking, you should take some comfortable shoes. The weather can also change quickly in this part of the country so it is important to take a jacket and umbrella in case it rains.
Driving tips
ou’ll encounter toll roads along your entire journey. There are toll roads and bridges in Illinois, Indiana, Ohio, Pennsylvania, New Jersey and New York. For most of the route, the speed limit is 70 miles per hour. However, once you get to New Jersey, the speed limit will drop to 65 mph.
What to know about the route
This 717-mile road trip will take you through island towns, state forests and major cities like Cleveland. Your journey will begin in Chicago and will then take you to South Bend, Indiana, the home of the University of Notre Dame. You can also tour a chocolate factory here and enjoy a few sweet treats. Next you’ll drive along Lake Erie and pass by Toledo, Ohio, on your way to Sandusky and Put-In-Bay Island where you can visit a theme park and enjoy activities like fishing, golfing and wine tasting. The next stop is Cleveland, Ohio, where you might catch a sporting event or visit an art museum. After leaving Cleveland you’ll stop at Moshannon State Forest. At this state park, you can go fishing, bird watching and camp. Your final stop on this excursion will be New York City. You can take a carriage ride in Central Park, explore museums or catch a Broadway show. Because it is such a long ride, you will want to drive a car that ensures that you have plenty of legroom, such as sedan or SUV.
Chicago
Chicago is a beautiful city that sits on Lake Michigan. With its many skyscrapers and tall buildings, it has a picturesque skyline. Fashionistas will find many designer shops and boutiques along The Magnificent Mile, aka, N. Michigan Avenue. Chicago also has a range of cultural and educational things to do and see including the Lincoln Park Zoo and several art museums.
Points of interest
You can start your vacation in downtown Chicago at Navy Pier. You’ll find a small amusement park here with rides and places to eat. Next, you can head to venues like the Art Institute of Chicago, the Field Museum or Shedd Aquarium. After dark, you can get lovely photographs of the skyline from the observation deck of the John Hancock Tower. You can also check our Chicago road trip guide for other interesting ideas.
Where to eat, drink and sleep
Chicago is known for its deep-dish pizza and delicious popcorn mixes. If you like hot dogs, you’ll enjoy eating the Chicago-style version, with a steamed bun and toppings like onions, pickles, tomatoes wedges, and mustard. Around the Magnificent Mile, you’ll find several hotels with rooftop bars and romantic views of the water and skyline. If you’re looking for a more affordable area to stay, the Lincoln Park or Lakeview neighborhoods might be ideal.
Sixt Insider Tip
Throughout Chicago and in the suburb of Oak Park, there are several Frank Lloyd Wright buildings. Frank Lloyd Wright was a famous architect known for his design of churches, schools, homes, and hotels. In Oak Park, you can take a walking tour to see many of the houses that he designed and visit his studio.
From Chicago to South Bend (96 miles)
Hop on I-90 East to continue your trip to New York City. Along the way, you’ll go through Gary, Indiana where you’ll find Lake Street Beach. The beach further provides access to the Indiana Dunes where you can take a relaxing stroll before you get back on the highway.
South Bend, IN
South Bend is home to the University of Notre Dame and its Golden Dome. South Bend sits on the St. Joseph River where you can enjoy a picturesque walk. In this college town, there are also many places to eat (especially pizzerias!) and lively nightlife.
Points of interest
Sports enthusiasts will want to try to catch a basketball, hockey or football game at the University of Notre Dame. Chocolate lovers will fall in love with the South Bend Chocolate Factory. Along with buying chocolates, you can tour the factory to see how chocolate treats are made. If you’re into history, you can visit the Studebaker National Museum and the Snite Museum of Art.
Sixt Insider Tip
Visit South Bend during Saint Patrick’s Day for lots of fun and excitement. You’ll find lots of people bar hopping and live music; the nickname of the Notre Dame football team is the Fighting Irish, after all!
From South Bend to Sandusky (203 miles)
Continue on I-90 East towards Ohio. Before you get to your next stop, Sandusky, you’ll go by Shipshewana. Shipshewana is an Amish community with quaint shops and restaurants. You can also purchase handmade goods here.
Sandusky, OH
Sandusky sits on the shore of Lake Erie. There are also several islands off the shore of the lake near Sandusky where you can enjoy activities such as golfing, fishing and boating. Sandusky is also home to a large amusement park with a private beach.
Points of interest
Visit the Cedar Point Amusement Park, sitting on a peninsula jutting into the lake, where you can get your thrills on a rollercoaster or watch a musical show. On warm days, the park provides access to the private Cedar Point Beach where you can sunbathe or take a swim. You can also take the ferry from Sandusky to nearby Put-In-Bay, which is an island on Lake Erie.
Sixt Insider Tip
Cedar Point offers a Fast Lane wristband that lets you move to the head of the line on all rides. Purchase your wristband in advance to get all the benefits. Since you’ll be driving on I-90, aka the Ohio Turnpike, you should know it has rest areas with its own gas stations, convenience stores and places to eat.
From Sandusky to Cleveland (62 miles)
You’ll hop back on I-80/90 going east to go to Cleveland. Along the way you’ll pass several small cities, the largest being Elyria and Lorain. These two cities are right off the interstate and have many fast-food restaurants where you can eat.
Cleveland, OH
The Cleveland metropolitan area also sits on the shores of Lake Erie. As well as being home to some popular museums, the city is also home to many professional sports teams including the Cleveland Browns (NFL), Cleveland Cavaliers (NBA) and the Cleveland Indians (MLB).
Points of interest
There are lots of fun things to do in Cleveland. You can visit the Rock and Roll Hall of Fame, a music museum covering the history of the rock genre and holding rare artifacts. There are also several art and history museums that you can tour including the Cleveland Museum of Art, the International Women’s Air & Space Museum and the Cleveland Museum of Natural History.
Where to eat, drink and sleep
Dine at the Hard Rock Café, which is connected to the Rock and Roll Hall of Fame. If you want to be within walking distance of numerous attractions, restaurants and bars, stay downtown where you’ll find several upscale hotels. You’ll also be close to FirstEnergy Stadium (Browns Stadium) and the Rocket Mortgage Field House (home of the Cleveland Cavaliers).
Sixt Insider Tip
Fans of the holiday movie classic, A Christmas Story, should be sure to visit the A Christmas Story house. The modest house is the same one used in the movie, and it’s now a museum where you can relive your favorite moments.
From Cleveland to Black Moshannon State Forest (226 miles)
Stay on I-80/I-90 traveling east toward Pennsylvania. Along the way you’ll go by Youngstown, Ohio. You can stop by Lanterman’s Mill and see the work of local craftsmen. This is also a good place to have a picnic if the weather permits.
Black Moshannon State Forest
Black Moshannon State Forest is in Clearfield County, Pennsylvania. It provides an opportunity to get out of the car and enjoy nature and the best part is it’s open year-round. A stream runs through the center of the forest making this a peaceful and serene place to visit.
Points of interest
You can enjoy a variety of recreational activities in the forest including fishing, mountain biking, hiking and bird watching. Also be on the lookout for creatures including deer, porcupines, flying squirrels, elk and bats at night.
From Black Moshannon State Forest to NYC (247 miles)
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New York City
The Big Apple is an exciting place to visit. It is known for its Broadway shows and theater district, historical landmarks, interesting and diverse museums and a skyline that will take your breath away. The city’s five boroughs are ethnically diverse and rich in cultures from around the world, making it an interesting place to visit.
Points of interest
There are numerous historical landmarks to visit on your travels to New York City. This includes the Statue of Liberty, the Empire State Building, the Brooklyn Bridge, the American Museum of Natural History and the Metropolitan Museum of Art. You’ll want to experience Times Square and its bright lights at night. If you’re interested in theater, you can take in a Broadway show after enjoying a carriage ride through Central Park.
Where to eat, drink and sleep
Most New Yorkers enjoy a bagel with cream cheese in the morning, but it has so much more to offer. Try a Nathan’s Famous hot dog, New York-style cheesecake, pizza and food from the many street carts around the city. On a romantic getaway, you might want to stay in a hotel close to Times Square or Central Park. If you’re looking to save a little money, you might book a boutique hotel across the river in Brooklyn.
Sixt Insider Tip
If you visit during the summer months, take the ferry from Battery Park or Brooklyn to Governors Island. This former US Army Base has been repurposed into a swath of green space where you can wander or ride a bike around and explore. Visit the Governors Island National Monument fort and grab a snack from one of the food trucks or other options you can find on the island.
