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How to get fromMilwaukee to Ossiningby plane, train, train (Amtrak), bus (Flixbus, Greyhound), car or bus

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There are 9 ways to get from Milwaukee to Ossining by plane, train, train (Amtrak), bus (Flixbus, Greyhound), car, or bus

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly General Mitchell International Airport to Laguardia Airport, train

    best
    1. Fly from General Mitchell International Airport (MKE) to Laguardia Airport (LGA)plane plane MKE - LGA
    2. Take the train from 125th Street - Harlem to Ossiningtrain train
    5h 26m
    $134–725

  2. Bus to Chicago O'Hare International Airport, fly to Laguardia Airport, train

    cheapest
    1. Take the bus from Milwaukee Intermodal/Amtrak Station to O'Hare International Airport - Terminal 2 Departuresbus bus
    2. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    3. Take the train from 125th Street - Harlem to Ossiningtrain train
    6h 46m
    $101–345

  3. Train (Amtrak)

    1. Take the train from Milwaukee to Chicago Union Stationtrain train Hiawatha Service / ...
    2. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    22h 9m
    $290–661

  4. Bus

    1. Take the bus from Milwaukee Intermodal Station to Chicago Bus Stationbus bus FlixBus 2548 / ...
    2. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640
    27h 15m
    $138–259

  5. Drive 899 mi

    1. Drive from Milwaukee to Ossiningcar car 899 mi
    15h 19m
    $165–237

  6. Fly General Mitchell International Airport to John F. Kennedy International Airport, train

    1. Fly from General Mitchell International Airport (MKE) to John F. Kennedy International Airport (JFK)plane plane MKE - JFK
    2. Take the train from Grand Central Terminal to Ossiningtrain train
    5h 46m
    $125–587

  7. Fly General Mitchell International Airport to Newark Liberty International Airport, train

    1. Fly from General Mitchell International Airport (MKE) to Newark Liberty International Airport (EWR)plane plane MKE - EWR
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Croton-Harmon Amtrak Stationtrain train
    6h 30m
    $132–610

  8. Bus to Chicago O'Hare International Airport, fly to John F. Kennedy International Airport, train

    1. Take the bus from Milwaukee Intermodal/Amtrak Station to O'Hare International Airport - Terminal 2 Departuresbus bus
    2. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    3. Take the train from Grand Central Terminal to Ossiningtrain train
    7h 8m
    $107–337

  9. Train to Chicago Midway International Airport, fly to Laguardia Airport, train

    1. Take the train from Milwaukee to Chicago Union Stationtrain train
    2. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    3. Take the train from 125th Street - Harlem to Ossiningtrain train
    7h 20m
    $123–559

Milwaukee to Ossining by train (Amtrak)

Calendar7Weekly Trains
Duration22h 9mAverage Duration
Ticket$290Cheapest Price
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Questions & Answers

What companies run services between Milwaukee, WI, USA and Ossining, NY, USA?

You can take a train from Milwaukee to Ossining via Chicago Union Station and Croton-Harmon in around 22h 9m. Alternatively, you can take a bus from Milwaukee Intermodal Station to Croton Ave @ S Highland Ave via Chicago Bus Station, New York Midtown, White Plains Bus Station, and White Plains Bus Terminal Lane E in around 27h 15m.

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