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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.
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.
You can pick from 5 daily train trips between New York and Chicago. The average train journey from New York to Chicago takes 22 hours and 45 minutes, but some Amtrak Lake Shore Limited train trips are as short as 19 hours and 32 minutes.
The best way to get from New York to Chicago is to fly which takes 4h 36m and costs $95 - $700. Alternatively, you can bus via Columbus, which costs $110 - $170 and takes 15h 10m, you could also train, which costs $85 - $290 and takes 19h 32m.
Find cheap train tickets to Chicago from New York. KAYAK searches hundreds of travel sites to help you find cheap train fares and book the train that suits you best.
Our data shows that the cheapest route for a one-way flight from New York to Chicago cost $54 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.
What is the cheapest flight from New York to Chicago O'Hare Intl Airport? In the last 3 days, the lowest price for a flight from New York to Chicago O'Hare Intl Airport was $31 for a one-way ticket and $69 for a round-trip.
