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  1. The Lake Shore Limited departs from NY Moynihan Train Hall at Penn Station in New York and arrives at Chicago (Union Station), Illinois in Chicago. The route takes about 19 hours and 32 minutes and ticket prices start at $84.

  2. Find trains to Chicago's Union Station from New York, Milwaukee, and 500 other cities. Plan your trip to Chicago and find the nearest train station today.

  3. Our data shows that the cheapest route for a one-way flight from New York to Chicago cost $55 and was between New York LaGuardia Airport and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly from New York LaGuardia Airport to Chicago Midway Airport.

  4. Compare your options: plane, train, bus, car, ferry, bike share, driving and walking directions all in one search. Train tickets from New York Penn Station to Chicago start at $86, and the quickest route takes just 19h 32m. Check timetables and book your tickets with Rome2Rio.

  5. Flights from New York to Chicago. Use Google Flights to plan your next trip and find cheap one way or round trip flights from New York to Chicago. Find the best flights fast,...

  6. There are 10 ways to get from Chicago to New York 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 Chicago Midway to New York La Guardia. 4h 21m. $98–673. cheapest. Fly Chicago Midway to Philadelphia, train. 5h 47m. $54–832.

  7. See maps and fares. Taxi, Lyft, and Uber pick-up points are available at both airports. Alternatively, you can e-hail and e-pay with CHICABS -approved apps ARRO and CURB. Credit cards are accepted in all taxis.