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How to get fromNew York Penn Station to 59th St.by train, plane, bus (Flixbus), train (Amtrak), car, or bus (Greyhound)

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There are 10 ways to get from New York Penn Station to 59th St. by train, plane, bus (Flixbus), train (Amtrak), car, or bus (Greyhound)

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 New York Penn Station to Flushing Main Streettrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    3. Take the train from Museum Campus/11th St. to 59th St.train train
    5h 18m
    $213–576

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

    cheapest
    1. Take the train from Grand Central Terminal to White Plainstrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 52m
    $107–497

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    18h 19m
    $146–237

  4. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    20h 45m
    $308–632

  5. Drive 783.1 mi

    1. Drive from New York Penn Station to 59th St.car car 783.1 mi
    13h 3m
    $143–207

  6. Fly Newark Liberty International Airport to Chicago O'Hare International Airport

    1. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    5h 32m
    $145–887

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

    1. Take the train from New York Penn Station to Flushing Main Streettrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    3. Take the train from Van Buren St. to 59th St.train train
    5h 46m
    $223–676

  8. Fly John F. Kennedy International Airport to Chicago O'Hare International Airport

    1. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    5h 39m
    $329–878

  9. Train to Philadelphia International Airport, fly to Chicago Midway International Airport

    1. Take the train from Ny Moynihan Train Hall At Penn Station to 30th Street Stationtrain train
    2. Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)plane plane PHL - MDW
    6h 13m
    $169–979

  10. Bus via Baltimore

    1. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus Greyhound US0670 / ...
    2. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus Greyhound US0164
    24h 30m
    $158–351

New York Penn Station to 59th St. by foot and bus (Flixbus)

Calendar30Weekly Services
Duration18h 19mAverage Duration
Ticket$146Cheapest Price
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Questions & Answers

Map of how to get from New York Penn Station to 59th St..ExpandLaunch map view
  • Distance: 753.5 mi
  • Duration: 5h 18m

What companies run services between New York Penn Station, NY, USA and 59th St., IL, USA?

Flixbus USA operates a bus from New York Midtown to Chicago Bus Station 4 times a day. Tickets cost $140–240 and the journey takes 16h 55m. Alternatively, Amtrak operates a train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station once daily. Tickets cost $300–650 and the journey takes 19h 32m.

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