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How to get fromTimes Square to Midtownby plane, train, bus (Flixbus), train (Amtrak), car, bus, shuttle, or bus (Greyhound)

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There are 12 ways to get from Times Square to Midtown by plane, train, bus (Flixbus), train (Amtrak), car, bus, shuttle, 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. Fly Laguardia Airport to Chicago Midway International Airport, train

    best
    1. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    2. Take the train from Van Buren St. to Gary Metro Centertrain train
    6h 25m
    $226–689

  2. Drive  761.9 mi

    cheapest
    1. Drive from Times Square to Midtowncar car 761.9 mi
    12h 36m
    $126–182

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Gary Bus Stationbus bus FlixBus N2641 / ...
    16h 14m
    $148–216

  4. Train via Ossining

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Croton-Harmon Amtrak Stationtrain train
    2. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train
    3. Take the train from Van Buren St. to Gary Metro Centertrain train
    21h 52m
    $539–853

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

    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
    3. Take the train from Van Buren St. to Gary Metro Centertrain train
    6h 27m
    $155–693

  6. Fly Laguardia Airport to Chicago O'Hare International Airport, train

    1. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    2. Take the train from Van Buren St. to Gary Metro Centertrain train
    6h 45m
    $146–499

  7. Fly John F. Kennedy International Airport to Chicago O'Hare International Airport, train

    1. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    2. Take the train from Van Buren St. to Gary Metro Centertrain train
    6h 28m
    $384–896

  8. Train to Philadelphia International Airport, fly to Chicago Midway International Airport, train

    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
    3. Take the train from Van Buren St. to Gary Metro Centertrain train
    7h 6m
    $193–998

  9. Fly Westchester County Airport to Chicago O'Hare International Airport, train

    1. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    2. Take the train from Van Buren St. to Gary Metro Centertrain train
    8h 22m
    $142–695

  10. Bus to Newark Liberty International Airport, fly to Indianapolis, shuttle, bus

    1. Take the bus from Port Authority Bus Terminal to Terminal Bbus bus
    2. Fly from Newark Liberty International Airport (EWR) to Indianapolis (IND)plane plane EWR - IND
    3. Take a shuttle bus from Indianapolis Airport to Holiday Inn City Centreshuttle bus
    4. Take the bus from Lafayette Bus Stop to Gary Bus Stationbus bus
    8h 41m
    $243–1,038

  11. Bus via Baltimore (Greyhound)

    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 Gary Bus Stationbus bus Greyhound US0164
    22h 24m
    $173–266

  12. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Dyer Stationtrain train Cardinal
    27h 33m
    $650–986

Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) flights

Calendar73Weekly Planes
Duration3h 1mAverage Duration
Ticket$105Cheapest Price
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Comparing Your Travel Options

Map of how to get from Times Square to Midtown.ExpandLaunch map view
  • Distance: 780.1 mi
  • Duration: 6h 25m

What companies run services between Times Square, NY, USA and Midtown, IN, USA?

Flixbus USA operates a bus from New York Midtown to Gary Bus Station once daily. Tickets cost $130–210 and the journey takes 16h 10m. Alternatively, you can take a train from Ny Moynihan Train Hall At Penn Station to Midtown via Croton-Harmon Amtrak Station, Chicago Union Station, Jackson & Clinton, Michigan & Van Buren/Ida B. Wells, Van Buren St., and Gary Metro Center in around 21h 52m.

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