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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 8 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)planeMKE - LGA
    2. Take the train from 125th Street - Harlem to Ossiningtrain
    5h 34m
    $144–583

  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
    2. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)planeORD - LGA
    3. Take the train from 125th Street - Harlem to Ossiningtrain
    6h 41m
    $102–321

  3. Train (Amtrak)

    1. Take the train from Milwaukee to Chicago Union StationtrainHiawatha Service / ...
    2. Take the train from Chicago Union Station to Croton-Harmon Amtrak StationtrainLake Shore Limited
    22h 9m
    $109–327

  4. Bus

    1. Take the bus from Milwaukee Intermodal Station to Chicago Bus StationbusFlixBus 2548 / ...
    2. Take the bus from Chicago Bus Station to New York MidtownbusFlixBus N2640
    27h 13m
    $132–291

  5. Drive 899 mi

    1. Drive from Milwaukee to Ossiningcar899 mi
    15h 8m
    $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)planeMKE - JFK
    2. Take the train from Grand Central Terminal to Ossiningtrain
    5h 54m
    $125–665

  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)planeMKE - EWR
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Croton-Harmon Amtrak Stationtrain
    6h 34m
    $202–709

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

    1. Take the train from Milwaukee to Chicago Union Stationtrain
    2. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)planeMDW - LGA
    3. Take the train from 125th Street - Harlem to Ossiningtrain
    7h 21m
    $112–485

Milwaukee to Ossining by train (Amtrak)

Calendar7Weekly Trains
Duration22h 9mAverage Duration
Ticket$109Cheapest 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 13m.

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