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How to get fromPenn Yan to Chicagoby car, plane, train, taxi, or bus

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There are 7 ways to get from Penn Yan to Chicago by car, plane, train, taxi, 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. Drive to Rochester, fly to Chicago Midway International Airport

    best
    1. Drive from Penn Yan to Rochester (ROC)car car
    2. Fly from Rochester (ROC) to Chicago Midway International Airport (MDW)plane plane ROC - MDW
    3h 49m
    $97–519

  2. Drive to Rochester, fly to Chicago O'Hare International Airport

    cheapest
    1. Drive from Penn Yan to Rochester (ROC)car car
    2. Fly from Rochester (ROC) to Chicago O'Hare International Airport (ORD)plane plane ROC - ORD
    4h 13m
    $77–429

  3. Drive, train (Amtrak)

    1. Drive from Penn Yan to Rochestercar car
    2. Take the train from Rochester to Chicago Union Stationtrain train Lake Shore Limited
    12h 55m
    $169–424

  4. Drive  632.9 mi

    1. Drive from Penn Yan to Chicagocar car 632.9 mi
    11h 3m
    $116–167

  5. Taxi to Elmira/Corning Regional Airport, fly to Chicago Midway International Airport

    1. Take the taxi from Penn Yan to Elmira/Corning Regional Airport (ELM)taxi taxi
    2. Fly from Elmira/Corning Regional Airport (ELM) to Chicago Midway International Airport (MDW)plane plane ELM - MDW
    6h 20m
    $148–467

  6. Drive, bus to Buffalo Niagara International Airport, fly to Chicago Midway International Airport

    1. Drive from Penn Yan to Rochestercar car
    2. Take the bus from Rochester to Buffalobus bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    5h 49m
    $189–368

  7. Drive, bus to Buffalo Niagara International Airport, fly to Chicago O'Hare International Airport

    1. Drive from Penn Yan to Rochestercar car
    2. Take the bus from Rochester to Buffalobus bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    6h 13m
    $199–358

Rochester (ROC) to Chicago Midway International Airport (MDW) flights

Calendar31Weekly Planes
Duration2h 55mAverage Duration
Ticket$87Cheapest Price
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Comparing Your Travel Options

Map of how to get from Penn Yan to Chicago.ExpandLaunch map view
  • Distance: 586.4 mi
  • Duration: 3h 49m

What companies run services between Penn Yan, NY, USA and Chicago, IL, USA?

There is no direct connection from Penn Yan to Chicago. However, you can drive to Rochester (ROC) airport, fly to Chicago Midway International Airport (MDW), walk to Midway, then take the subway to Harold Washington Library. Alternatively, you can take a vehicle from Penn Yan to Chicago Union Station via Rochester in around 12h 55m.

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