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How to get fromTimes Square to 59th St.by subway, plane, train, train (Amtrak), bus (Flixbus), car, bus, or bus (Greyhound, Amtrak)

Find Transport to 59th St.

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There are 10 ways to get from Times Square to 59th St. by subway, plane, train, train (Amtrak), bus (Flixbus), car, bus, or bus (Greyhound, Amtrak)

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

  1. Line 7 subway to Laguardia Airport, fly to Chicago Midway International Airport, train

    best
    1. Take the subway from 42 St-Times Square to Flushing-Main Stsubway subway
    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 33m
    $211–671

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

    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
    3. Take the train from Van Buren St. to 59th St.train train
    7h 28m
    $117–627

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    20h 45m
    $255–559

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    21h 39m
    $152–239

  5. Drive  782.9 mi

    1. Drive from Times Square to 59th St.car car 782.9 mi
    13h 1m
    $143–207

  6. Line 7 subway to Laguardia Airport, fly to Chicago O'Hare International Airport, train

    1. Take the subway from 42 St-Times Square to Flushing-Main Stsubway subway
    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 53m
    $141–571

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

    1. Take the bus from Port Authority Bus Terminal to Terminal Bbus bus
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    5h 44m
    $150–925

  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 41m
    $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 14m
    $169–979

  10. Bus via Toledo

    1. Take the bus from Port Authority Bus Terminal to Toledo Bus Stopbus bus Greyhound US0420
    2. Take the bus from Toledo to Chicago Union Stationbus bus Amtrak Thruway Connecting Service
    22h 45m
    $176–303

Times Square to 59th St. by train and bus (Amtrak)

Calendar10Weekly Services
Duration20h 45mAverage Duration
Ticket$255Cheapest Price
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Questions & Answers

Map of how to get from Times Square to 59th St..ExpandLaunch map view
  • Distance: 753.5 mi
  • Duration: 5h 33m

What companies run services between Times Square, NY, USA and 59th St., IL, USA?

Amtrak operates a train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station once daily. Tickets cost $250–600 and the journey takes 19h 32m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $140–240 and the journey takes 20h 25m.

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