Rome2Rio

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

Find Transport to 59th St.

See all options

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)

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 42m

  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 39m
    $80–373

  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
    $127–504

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicagobus bus FlixBus N2640
    21h
    $112–180

  5. Drive 782.7 mi

    1. Drive from Times Square to 59th St.car car 782.7 mi
    12h 54m
    $143–207

  6. Subway, bus to Laguardia Airport, fly to Chicago O'Hare International Airport, train

    1. Take the subway from 42 St-Port Authority Bus Terminal to 125 Stsubway subway
    2. Take the bus from W 125 St/Saint Nicholas Av to Laguardia Rd/94 Stbus bus
    3. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    4. Take the train from Van Buren St. to 59th St.train train
    5h 59m

  7. Subway, bus to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the subway from 42 St-Port Authority Bus Terminal to 125 Stsubway subway
    2. Take the bus from W 125 St/Saint Nicholas Av to Laguardia Rd/94 Stbus bus
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 47m
    $87–465

  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 49m
    $816–1,023

  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 37m
    $100–1,061

  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 16m
    $111–317

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

Calendar10Weekly Services
Duration20h 45mAverage Duration
Ticket$127Cheapest Price
See schedules

Questions & Answers

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 $120–500 and the journey takes 19h 32m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago once daily. Tickets cost $110–180 and the journey takes 19h 55m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

More Questions & Answers

Trips from Times Square

Trips to 59th St.

Popular routes