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How to get fromPoughkeepsie to Waukeganby train, plane, train (Amtrak), bus (Flixbus) or car

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There are 9 ways to get from Poughkeepsie to Waukegan by train, plane, train (Amtrak), bus (Flixbus), or car

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

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

    best
    1. Take the train from Poughkeepsie to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)planeLGA - MDW
    3. Take the train from Chicago OTC to Waukegantrain
    8h 34m
    $99–445

  2. Train

    cheapest
    1. Take the train from Poughkeepsie Amtrak Station to Chicago Union StationtrainLake Shore Limited
    2. Take the train from Chicago OTC to WaukegantrainUp-N
    20h 1m
    $72–291

  3. Bus

    1. Take the bus from Metro North Station to TransCenterbusWpp
    2. Take the bus from New York Midtown to Chicagobus
    3. Take the bus from Tornado Bus Co - Chicago to Tornado Bus Co - Waukeganbus
    28h 3m
    $158–336

  4. Drive 852.2 mi

    1. Drive from Poughkeepsie to Waukegancar852.2 mi
    14h 14m
    $156–225

  5. Train to Laguardia Airport, fly to Chicago O'Hare International Airport, train

    1. Take the train from Poughkeepsie to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)planeLGA - ORD
    3. Take the train from Clybourn to Waukegantrain
    8h 38m

  6. Train to Albany County Airport, fly to Chicago Midway International Airport, train

    1. Take the train from Poughkeepsie Amtrak Station to Albany-Rensselaer Amtrak Stationtrain
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)planeALB - MDW
    3. Take the train from Chicago OTC to Waukegantrain
    8h 53m
    $134–694

  7. Train to Newark Liberty International Airport, fly to Chicago O'Hare International Airport, train

    1. Take the train from Poughkeepsie Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)planeEWR - ORD
    3. Take the train from Clybourn to Waukegantrain
    9h 16m

  8. Train to Albany County Airport, fly to Chicago O'Hare International Airport, train

    1. Take the train from Poughkeepsie Amtrak Station to Albany-Rensselaer Amtrak Stationtrain
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)planeALB - ORD
    3. Take the train from Clybourn to Waukegantrain
    9h 19m

  9. Train to Westchester County Airport, fly to Chicago O'Hare International Airport, train

    1. Take the train from Poughkeepsie to 125th Street - Harlemtrain
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)planeHPN - ORD
    3. Take the train from Clybourn to Waukegantrain
    10h 43m

Poughkeepsie to Waukegan by train and foot

Calendar7Weekly Services
Duration20h 1mAverage Duration
Ticket$72Cheapest Price
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Questions & Answers

What companies run services between Poughkeepsie, NY, USA and Waukegan, IL, USA?

You can take a train from Poughkeepsie Amtrak Station to Waukegan via Chicago Union Station and Chicago OTC in around 20h 1m. Alternatively, you can take a bus from Metro North Station to Tornado Bus Co - Waukegan via TransCenter, White Plains Bus Station, New York Midtown, Chicago, State & 95th Street, 35th Street & Cottage Grove, California & 35th Street, and Tornado Bus Co - Chicago in around 28h 3m.

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