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American Airlines, JetBlue Airways, and Delta fly from New York JFK (JFK) to Chicago O'Hare (ORD) every 2 hours. Alternatively, Amtrak operates a train from New York Penn Station to Chicago Union Station once daily.
There are 10 ways to get from New York to Chicago by plane, train, bus, or car. Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner. best. Fly New York La Guardia to Chicago Midway. 4h 36m. $97–665. cheapest. Train to Philadelphia, fly to Chicago Midway. 5h 38m. $55–852.
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Are you searching for American Airlines flights from New York to Chicago? Find the best selections and fly in style.
There are 9 ways to get from Manhattan to Chicago by plane, train, bus, or car. Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner. best. Fly New York La Guardia to Chicago Midway. 4h 22m. $97–665. cheapest. Train to Philadelphia, fly to Chicago Midway. 5h 58m. $57–825.
Despite being costlier than the subway, LIRR has more space for luggage, and it is considered the fastest transit option for journeys from JFK to downtown NYC. LIRR is the busiest commuter train in the northern part of America, with 735 everyday routes.
Buy train tickets to Chicago on Amtrak.com, from the Amtrak app, at an Amtrak kiosk or from a ticketing agent at any Amtrak station. Popular Train Trips to Chicago. Ann Arbor, MI to Chicago, IL. Detroit, MI to Chicago, IL. Milwaukee, WI to Chicago, IL.
