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Search for cheap train tickets from new york to chicago and book your trip in minutes. Search chicago trains on kayak. 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. You can pick from 3 daily train trips between new york and chicago. The average train journey from new york to chicago takes 22 hours and 23 minutes, but some amtrak lake shore. New york to chicago train services, operated by amtrak, depart from ny moynihan train hall at penn station. Train, bus or fly from new york to chicago? The best way to get from new york. Book a cheap train ticket from new york, ny to chicago, il from $38 (โฌ35) with amtrak. Search train times and schedules and travel by train from new york, ny to chicago,.