Possibly your ancestor took a ferry to the Battery in Manhattan and then departed for Chicago via the Pennsylvania RR from Pennsylvania Station in NYC or another possibility would be the New York Central which would have left from Grand Central Station. Or if they were given leave from Ellis Island to New Jersey, maybe they met the Pennsylvania RR train in Newark, NJ.
Subway transport to either NY railroad station was not available prior to 1898, one would have used streetcars. They may have been electric depending on the year of departure.
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