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

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There are 11 ways to get from Times Square to Midtown by plane, train, bus (Flixbus), train (Amtrak), car, bus, 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 27m
    $114–517

  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 Gary Metro Centertrain train
    8h 16m
    $107–445

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Gary Bus Stationbus bus FlixBus N2642 / ...
    21h 39m
    $152–246

  4. Train via Ossining

    1. Take the train from Grand Central Terminal to Croton-Harmontrain 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 Ssl
    22h 2m
    $321–642

  5. Drive 761.7 mi

    1. Drive from Times Square to Midtowncar car 761.7 mi
    12h 37m
    $139–201

  6. 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 31m
    $134–382

  7. 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 46m
    $119–277

  8. 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
    $683–895

  9. 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 4m
    $153–1,226

  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 Gary Bus Stationbus bus Greyhound US0164
    21h 59m
    $155–333

  11. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Dyer Stationtrain train Cardinal
    27h 33m
    $389–752

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

Calendar68Weekly Planes
Duration2h 51mAverage Duration
Ticket$92Cheapest Price
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Questions & Answers

Map of how to get from Times Square to Midtown.ExpandLaunch map view
  • Distance: 780.1 mi
  • Duration: 6h 27m

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 twice daily. Tickets cost $140–240 and the journey takes 21h 35m. Alternatively, you can take a train from Grand Central Terminal 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 22h 2m.

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