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How to get fromTimes Square to 59th St.by bus, plane, train (Amtrak), bus (Flixbus), car, subway, train, 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 bus, plane, train (Amtrak), bus (Flixbus), car, subway, train, 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. Bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    best
    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 40m
    $150–925

  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 33m
    $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
    $532–815

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    21h 17m
    $154–228

  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 Midway International Airport

    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
    5h 36m
    $211–671

  7. 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
    6h 1m
    $141–571

  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 44m
    $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 18m
    $168–980

  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

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

Calendar10Weekly Services
Duration20h 45mAverage Duration
Ticket$532Cheapest Price
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Comparing Your Travel Options

Map of how to get from Times Square to 59th St..ExpandLaunch map view
  • Distance: 803.9 mi
  • Duration: 5h 40m

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 $500–850 and the journey takes 19h 32m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $140–230 and the journey takes 20h 25m.

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