3 ways to get from New York City to Chicago
Here’s the lowdown on making the journey by plane, train, or car.
Depending on whether you travel by plane, train, or car, the journey from New York City to Chicago can be a means to an end or an adventure in itself. Below, we’ve condensed all the information you need to make your transport decision, from logistical considerations (journey time and average costs) to pleasurable perks (cultural and culinary stops).
New York City to Chicago by plane
With dozens of daily flights from NYC to Chicago, you likely won’t have any trouble finding flight times to suit your plans. Budget-wise, the most affordable (and chilliest) months to travel are January and February, when roundtrip flights start at approximately $170. Expect to fork out another $50–100 for round trips during spring and early fall. One-way flights from NYC to Chicago tend to hover around $100 or less.
With a duration of approximately two hours and 45 minutes, a flight is the quickest way to travel between the two cities. There are technically six airports local to Chicago, but most planes from New York’s John F. Kennedy (JFK) or LaGuardia (LGA) airports land in either O'Hare International (ORD) or Midway International (MDW). (In nearby Newark, NJ, Newark Liberty International Airport also has regularly scheduled flights to Chicago.)
Once you touch down, frequent trains will take you into the heart of the city quickly and cheaply (and at just $2.25–$5 per ticket, the price can’t be beaten). From O'Hare, catch the 24-hour Blue Line train, which arrives in the downtown area in 45 minutes. From Midway, the Orange Line train will whisk you into Chicago proper in under half an hour. If you’d like, you can also grab a taxi or ride-share service to take you to downtown Chicago, but you’ll likely face some traffic.
New York City to Chicago by car
If you were to drive the 850-plus miles between New York City and Chicago without stopping, it would take approximately 13 hours. But why would you do that when there are plenty of interesting places to stop on your journey west?
Leave NYC via the Holland Tunnel and head towards Harrisburg, PA, where you could stop at the National Civil War Museum or take a quick detour to nearby Hershey's Chocolate World, before getting on I-76 West.
Follow signs for Pittsburgh, which is a good place to stop for the night after 370 miles of driving. Book a night at the Kimpton Hotel Monaco Pittsburgh, a stone’s throw from Acrisure Stadium, PNC Park, and the vibrant restaurant scene of Pittsburgh’s Cultural District. If you have time, take a tour with Walk the Burgh of this fascinating and historic nabe.
Alternatively, continue your journey along the I-76 West for another hour or so, following signs to Cleveland. Check into the Aloft Cleveland Downtown and visit the nearby Rock & Roll Hall of Fame or catch a show at Playhouse Square—the largest performing arts center in the nation outside of New York. Outdoorsy types may want to swing by Cuyahoga Valley National Park (about a half-hour outside of Cleveland), which our community members praise for “awesome geological features” and being “small, but worth the stop.”
The following morning, pass through South Bend, IN, where you can stop for food at LaSalle Grill and wander around the University of Notre Dame. Then, set your GPS for Indiana Dunes State Park—three miles of beautiful beach that hugs Lake Michigan’s southern shore. After you’ve stretched your legs and dipped your toes in the water, hop back in the car for the final 50 miles to Chicago.
New York City to Chicago by train
A train journey on Amtrak is by far the most time-consuming way to travel from New York City to Chicago, clocking in at around 22 hours and 50 minutes (though the Amtrak Lake Shore Limited train is a couple of hours faster than other routes, taking about 19 hours and 30 minutes on average).
Five trains depart NYC’s Penn Station daily, bound for Chicago’s Union Station. The cheapest month to make the journey is January, when a return ticket costs around $120. In April, prices creep up to the $200 mark, though you can potentially travel for less if you book at least a month before your intended departure date.
Given the journey time you might want to consider booking one of Amtrak’s roomettes (private rooms with a fold-out bed and teeny bathroom, which include meals and turndown service), if your budget is flexible—they can cost upwards of $500.