How to Travel from New York to Chicago by Train, Bus, Car, and Plane

The Windy City of Chicago is 790 miles west of New York City. To get from New York City to Chicago, there are several transportation options. Consider the pros and cons of each option to choose the best transportation choice for you, depending on budget and time constraints. Flying will certainly take the least amount of time (about 3 hours) but it can be expensive, unless you catch a good deal. Buses and trains take the longest (at least 19 hours and often longer) and the bus is the likely the cheapest choice, especially if you can’t drive. But it’s also the least comfortable. The train is more comfortable than a bus, yet will certainly be pricier. Driving takes about 12 hours without stopping, and it’s not the most scenic part of the country for a road trip. That said, it is certainly faster than the bus and could end up being even cheaper, depending on how many people are splitting the costs.

What Is the Cheapest Way to Get From New York to Chicago?

Bus service from New York City to Chicago is a long journey, but it is also the cheapest travel option, with one-way tickets starting at $38. Trips take between 19 and 23 hours, with at least one transfer. There are no sleeper options, only regular seats, making this a long, uncomfortable ride. However, it might be the cheapest way of getting there if flights are expensive and you don’t have your own car. Greyhound is the only company that services this route and buses depart from Port Authority Bus Terminal in Manhattan and arrive at one of two bus stations or Union Station. These buses offer Wi-Fi service.

What Is the Fastest Way to Get From New York to Chicago?

Flying to and from Chicago is the fastest and most convenient way to travel there from New York City. While it is usually more expensive than the bus or driving, it is much, much faster. And it’s often cheaper and always much quicker than the train. The flight takes about 3 hours (and about 2.5 hours from Chicago to New York because of tailwinds), but that does not include time spent getting to and from the airport, checking bags, or clearing security. All of the major carriers, including JetBlue, Delta, United, and American Airlines, as well as budget carriers including Southwest and Spirit Airlines, service the route, with one-way fares as low as $48—but it can go up to over $200 from there. Chicago O’Hare International Airport (ORD) is the largest airport (and one of the busiest in the world) and is 15 miles away from downtown. Chicago Midway Airport is smaller and has fewer flights, but it’s closer to the city (11 miles).

How Long Does It Take to Drive?

You can drive between New York City and Chicago in about 12 hours without stopping. It’s pretty much a straight shot west on I-80, taking you through New Jersey, Pennsylvania, and Ohio, and then along the Michigan and Indiana border until you go around the southern tip of Lake Michigan and back up into Chicago. The journey is about 790 miles. Obviously on a drive this long—at least 12 hours—you’re bound to hit several rush hours and traffic along the way. You should decide if you want to stay over one night along the way to break up the trip, which, unless you’re in a hurry, probably makes sense. Visitors to New York City can rent cars in Manhattan, although rates at the airports tend to be cheaper.

While this trip is long, the most significant advantage of traveling via car is that there is no schedule to stick to, and there are a few interesting places to stop along the way. You might save some money driving by car, especially if you don’t have to rent one and are traveling with a group of people who can share the costs. Remember to add gas and tolls into your budget, along with snacks, meals, and accommodations if you decide to stay overnight along the way. Camping or staying with friends can reduce costs.

How Long Is the Train Ride?

Traveling by train to and from Chicago and New York City is a relatively long journey and often not very affordable, making this the least convenient option, as well as one of the priciest. Trains go from Penn Station in Manhattan to Chicago Union Station in downtown Chicago. The route is serviced by Amtrak, via the Lake Shore Limited or Cardinal to Chicago or by changing trains either in Washington, D.C. or Pittsburgh. The shortest and most direct trip is on the Lake Shore Limited, and it takes about 19 hours, with stops including Boston, Buffalo, Cleveland, and South Bend, Indiana. Tickets range from $112 for a seat to $380 and up for a sleeper car for one-way. Many find train travel romantic, but this might not be the best route for that dream train trip as it is not the most scenic. These trains offer Wi-Fi service. You can purchase tickets in advance by Amtrak or in person at Penn Station.

When Is the Best Time to Travel to Chicago?

The best time to visit Chicago is in the late spring or early fall, from September through November. At these times of year, temperatures are pleasant and the city isn't overly crowded. There is also an excellent mix of events, festivals, and sports.

What Time Is It in Chicago?

Chicago is located in Central Daylight Time, so it is one hour behind New York. For example, if it is 12 p.m. in New York, it is 11 a.m. in Chicago.

Can I Use Public Transportation to Travel From the Airport?

You can get to the downtown Chicago from O’Hare on the Blue Line train of Chicago Transit Authority (CTA) in about 45 minutes. There are also various shuttle bus options, including GO Airport Shuttle and Airport Supersaver. Or you can take a taxi, Uber, or Lyft, or rent a car. The drive to the city usually takes about 25 minutes, depending on traffic.

What Is There to Do in Chicago?

Chicago is one of the United States’ most popular cities. More than just deep dish pizza and Chicago dogs (although you should sample both), Chicago has a wide variety of attractions, museums, restaurants, and nightlife. Chicago is a big city full of impressive architecture and soaring skyscrapers, including one of the world’s tallest (Willis Tower)—take an architectural boat tour to learn the city’s history and see its most iconic buildings. It is also home to must-see museums like the Art Institute of Chicago, the Field Museum, Shedd Aquarium, and the Museum of Science and Industry. Stroll the Magnificent Mile for historic buildings mingling with bustling shops and restaurants. The city has plenty of outdoor attractions as well, including beaches dotting the shoreline of Lake Michigan, Millennium Park, the 606, Navy Pier, Chicago Riverwalk, and Humboldt Park. And don’t forget to take in a game at historic Wrigley Field and sample some of the best restaurants and bars in the country.