New York is one of the most famous cities in the world and Manhattan is one of the most visited places in the world. Many prefer to fly from Chicago to New York rather than New York to see all the sights.

That would be a big mistake, because the road from Chicago to New York runs through at least 6 states and opens up incredible landscapes, from the Great Lakes to historic cities.

An 805 mile journey from Chicago to New York City can be completed in just over 12 hours of clean driving, but you’ll need to stop for a few days along the Great Lakes in Pittsburgh, Philadelphia, and visit the beautiful national parks along the way.

Read on for directions, places and sights along the way and the best tips for the long journey from Illinois to New York.

What is the distance between New York and Chicago and how long does it take to get there?

When you travel from the third city in the United States to the first, you may feel that the difference will be insignificant. It’s only when you realize that New York has more than three times the population of Chicago that you begin to feel how unique that city is.

The fastest and shortest route between Chicago and New York City is 805 miles and takes 12 to 13 hours to count, refuel and stop for food.

The Skyway Bridge along the I-90 in Chicago on a beautiful day.
Start your journey from Chicago to New York by crossing the Chicago Skyway Bridge to Indiana.

Henryk Sadura/Shutterstock.com

However, making this trip almost exclusively on one of the main roads does not feel like a journey – if your only goal is to get from point A to point B, you could fly. So we’re going to shake it up and choose a more picturesque route, where there’s a lot to do and see along the way.

The best route from Chicago to New York is in the shade for less than 900 miles and takes 14 to 15 hours. With 3 stops for fuel, meal breaks and rest, you’ll be waiting for about 20 hours on the road.

Best route from Chicago to New York

The beginning of our journey is almost painfully simple. You take the I-90 east of Chicago, through the southern tip of Lake Michigan, and drive almost 350 miles to Cleveland, Ohio.

From there take the I-77 to the south, to the I-80 at Cuyahoga Valley National Park. Follow the road to the Ohio exit just before the Meander Creek Reservoir and take the I-76.

You do most of the 40 miles before you get to I-79, and then you go back to I-279, which will take you to Pittsburgh.

If you’re leaving Pittsburgh, take the I-376 eastbound until you get back on the I-76 we were on earlier. Follow the Interstate Highway for nearly 300 miles through Pennsylvania to the historic city of Philadelphia.

If you want to spend some time exploring, take a little detour and visit Amish land on the road.

After Philadelphia take the I-95 via Princeton to Newark, from where you can choose from several bridges across the Hudson River to Manhattan.

Best stops between Chicago and New York

So even if technically you can travel in one day, especially if you use a direct route, it will not be equally fun for all participants.

The most common strategy likely to be followed is to divide the trip into two days, with a stop at an intermediate point.

But since we are on our way, it is better to get the most out of our trip than to arrive quickly, and the division in 3 days allows us to do so.

For some, even three days might not be enough. Let’s say we stop in three places without saying how many days it will take.

Overnight stay in Cleveland, Ohio

For just over a third of our trip this is the perfect place to camp for the first time.

Cleveland, the 15th largest city in the United States, is the best-selling city because it lies on the shores of Lake Erie.

There are many museums, a botanical garden, and even the Rock and Roll Hall of Fame, and you have something to do in town.

The Rock and Roll Hall of Fame in Cleveland with its pyramidal structure on a sunny day.
Whether you’re a music lover or not, if you’re in Cleveland, the Rock ‘n’ Roll Music Hall is a must, either by its nature or its beautiful structure.

Allen.G/Shutterstock.com

Or maybe you should just move between two big cities? If so, why not take a boat trip on Lake Erie and discover the fantastic sights and sounds of one of the five Great Lakes.

Just over 20 minutes from the city is the Cuyahoga Valley National Park, where you can walk through the hills and vast forests where deer, beavers, foxes and an incredible population of 250 species of birds live, including the legendary white-tailed eagle.

Whatever you decide to do during the day, I strongly advise you to go into the hidden house at night when you’re done.

A beautiful Gothic mansion from the early 1900’s, within walking distance of some of the city’s most famous landmarks, beautifully decorated rooms and Glidden House Park will make you feel like a royal family. There is even a free breakfast in their luxurious dining room.

If you’re traveling in the run-up to Christmas, the house is fabulously decorated – the perfect treat to prepare for what awaits you in New York.

Experience of the way of life of the Emir

Then in Pennsylvania, on the road from Pittsburgh to Philadelphia, is the town of Lancaster. Unlike Chicago and New York and other stops on the road, Lancaster is not an important junction. Instead, Lancaster is home to the largest Amish community in the United States.

Two Amish males and a female take care of their horses on a sunny day in Lancaster, Pennsylvania.
The Amish of Lancaster, Pennsylvania, are mainly active in agriculture.

Vadim 777/Shutterstock.com

What a wonderful opportunity to learn first hand about the history and culture of a unique group of people.

You will have the chance to see their famous horse-drawn carriages, their primitive farming techniques and just an ordinary way of life more reminiscent of the simpler times of a forgotten era.

If you’re lucky, you might even get a tour with an Amish guide who will show you the sites and explain why they live the way they do.

You can immerse yourself even more in the past by spending a night at the Fulton Steamboat Inn. Authentic steamer with luxurious Victorian-style rooms, equipped with modern luxury amenities including a flat-screen TV, indoor pool and gym.

Staying here allows you to stay in the spirit of things while enjoying all the comforts necessary for a well-earned rest.

Immersion in American history in Philadelphia

Because Philadelphia is one of the most fascinating cities in the country, full of culture and history, you really should make Philadelphia a stop on your trip from Chicago to New York.

Philadelphia, the sixth largest city in America to date, was one of the first cities in the country and was founded in 1682 by the famous writer William Penn.

Independence Hall in the National Historical Park on a sunny day with some visitors.
Philadelphia Independence Hall is one of the mandatory stops on the way to the historic city.

f11photo/Shutterstock.com

Explore the rich history of the National Independence Historical Park, home to monuments such as the Liberty Bell and Independence Hall, where the Declaration of Independence and the U.S. Constitution were adopted, a copy of which you can see during your visit.

Although there are a number of large and fantastic hotel chains in the city, I personally enjoyed my stay at the Dwight D Boutique Hotel. It’s a little further away from the historic sights, but right next to some great restaurants between Rittenhouse Square and City Hall.

The luxurious rooms and the hotel are so small that you can really feel the personal touch of the owners, although I prefer the feeling of anonymity that comes from sitting in one of the 300 identical rooms in a large network.

What to see on a trip from Chicago to New York

While you probably want to get to New York quickly to enjoy all that this great city has to offer, you should take the time to explore some of the fantastic places you’ll discover on your trip – that’s what it’s all about, isn’t it?

  1. Lake Michigan – The first part of your trip will take place around the southern tip of Lake Michigan, the second largest of the Great Lakes and the only one entirely within the United States.
  2. Indiana Dunes National Park – Indiana Dunes, the second newest addition to the national park register, represents nearly 25 miles of sand dunes stretching along the shores of Lake Michigan’s southeastern shore.
  3. Toledo, Ohio – Toledo is the fourth city in Ohio. It is famous for its history of jazz music and has museums, galleries and bars dedicated to it.
  4. Lake Erie – With an area of 9,910 miles, Lake Erie is the second largest of the Great Lakes, but it is still a beautiful sight to see.
  5. Cleveland, Ohio is the largest urban area in Ohio.
  6. Cuyahoga Valley National Park – 51 square miles of farmland, forests and hills with an incredible concentration of wildlife along the banks of the Cuyahoga River.
  7. Pittsburgh – A city of steel, Pittsburgh is famous for its steel construction, incredible architecture and collection of 446 bridges.
  8. Susquehanna – The longest river on the east coast of the United States, the Susquehanna, stretches 444 miles from Cooperstown, New York to Susquehanna Park, Maryland.
  9. Lancaster, Pennsylvania – The largest Amish colony in the United States, takes the opportunity to discover their totally different culture.
  10. Washington, D.C. by-pass, – A relatively short detour on this scenic route takes you to the capital, with its architecture and huge museums.
  11. Philadelphia – Philadelphia, known as the City of Brotherly Love, is the largest city in Pennsylvania and the sixth largest city in the United States in terms of population.
  12. Princeton – If you are driving through New Jersey on the last stretch of the road to New York City, Princeton College is the perfect place to stop for lunch.
  13. Delaware River – The river forms a long stretch of the New York-Hill border and several beautiful towns (Hello, Calliquin) as well as a famous stretch of the winding road called Hawke’s Nest.
  14. Catskills – If you take the quickest route or go further north, the Catskills are beautiful mountains near the Big Apple, where wealthy New Yorkers ski in winter.

Water licking the trees at Brandywine Falls in Cuyahoga Valley National Park on a sunny day.
Make the most of your stay in Ohio overlooking the breathtaking Brandevine Falls in Cuyahoga Valley National Park.

Ashley Marie Best/Shutterstock.com

Best time to travel from Chicago to New York

If you are travelling to the city, the weather is less important than, for example, for a beach holiday, so you can go at any time. However, there are two separate issues that may influence your decision.

New York is a place that really comes alive around Christmas. Whether it’s a fantastic light show on Saxon Fifth Avenue, a Christmas tree and a skating rink at the Rockefeller Center.

Despite the fact that this theme is shared by the locals, a horse-drawn carriage ride through the snow-covered Central Park is a unique magical event.

Don’t forget that New York City can be ridiculously busy with tourists around Christmas. I lived in New York City myself, and I can say I didn’t see as many places as New York City in mid-December.

In summer the weather will be excellent for your whole trip and will also give you the opportunity to visit some of the national parks that you will cross and explore the surrounding countryside in general.

To get the best weather balance and avoid crowds, I would go in September or early October – crowds really die after Labor Day, and September is always nice weather when you’re finally in New York.

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