Getting from New York City to Chicago

New York to Chicago is one of the busiest air routes in the country, and flying is how nearly everyone does it. You can also take the train, the bus or the interstate, and each makes sense for somebody. All three take most of a day, or longer.

For the Chicago end, see getting to Chicago for the stations and our airports page for the trains from O'Hare and Midway into the Loop.

Flying

O'Hare is LaGuardia's busiest route, with about 1.36 million passengers between June 2025 and May 2026 (Wikipedia). American, Delta and United all fly it, and Southwest flies from LaGuardia to Midway.

The other two airports work too. From JFK, American and Delta Connection fly to O'Hare. From Newark, United and American fly to O'Hare, and Frontier flies to Midway. Pick the airport that's easiest for you to reach, then compare. Search "New York (NYC)" to "Chicago (CHI)" and you'll see all three airports and both Chicago ones at once. Plan on about two and a half hours in the air heading west, a bit less coming back.

The old version of this page quoted fares, and we've dropped them because they move by the hour. In short, January through early March is cheap, and Lollapalooza weekend and Chicago Marathon weekend aren't. The flights page has the rest.

By train

Two Amtrak trains run between New York and Chicago, and neither is quick.

The Lake Shore Limited is the daily one. It leaves Moynihan Train Hall at Penn Station in the afternoon, runs up the Hudson to Albany, west past Syracuse and Buffalo overnight, along Lake Erie through Cleveland and Toledo, and reaches Chicago Union Station mid-morning. It takes about 19 and a half hours westbound and a little over 20 heading east. The Hudson River stretch at the start is the best part, so get a seat on the left side of the train leaving New York.

The Cardinal is the scenic one, and it runs only three days a week, leaving New York on Wednesday, Friday and Sunday mornings. It goes south through Philadelphia and Washington, then west through the Virginia horse country, the Blue Ridge and West Virginia's New River Gorge, before an overnight run through Cincinnati and Indianapolis into Chicago. That's more than a day on the train. People ride it for the mountains, not to get anywhere fast.

A roomette on either train buys you a bed and your meals, and in most seasons it costs well above a flight. In coach, you're sleeping sitting up. It's worth it only if the trip itself is the point.

By bus

FlixBus and Greyhound, which share a booking site, list more than 30 trips a day between the two cities. The quickest takes about 17 hours. In New York, buses use the Port Authority Bus Terminal at 625 8th Ave. and a curbside stop at 31st Street and 8th Avenue, across from Moynihan. In Chicago, you'll end up at the Greyhound station at 630 W. Harrison St. or the stop outside Union Station. It's the cheapest way to make the trip and also the most tiring, and once you've paid for food along the way, a sale fare on a flight is often close.

Driving

It's about 790 miles, mostly on I-80. You cross New Jersey and the full width of Pennsylvania on I-80, pick up the Ohio Turnpike near Youngstown, and finish on the Indiana Toll Road and the Chicago Skyway. The first version of this page had the route running through Michigan. It doesn't. Figure 12 to 13 hours of driving, so most people split it with a night somewhere in Ohio. The Ohio and Indiana toll roads and the Skyway all take E-ZPass. You gain an hour partway across northwest Indiana, where the clocks switch to Central Time, not at the state line.

Once you're in Chicago, a car is mostly a parking bill. Leave it at the hotel or a booked garage and use the L. Our transportation page covers getting around.

Photo by caruba