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

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There are 11 ways to get from Times Square to Midtown by bus, plane, train, bus (Flixbus), train (Amtrak), car, 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, train

    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
    3. Take the train from Van Buren St. to Gary Metro Centertrain train
    6h 18m
    $94–332

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

    cheapest
    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 55m
    $69–317

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Merrillvillebus bus FlixBus N2640
    19h 23m
    $142–228

  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 27m
    $231–512

  5. Drive 761.7 mi

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

  6. Fly Laguardia Airport to Chicago Midway International Airport, train

    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 35m
    $119–587

  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 26m
    $78–305

  8. Bus to Newark Liberty International Airport, fly to Chicago Midway 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 Midway International Airport (MDW)plane plane EWR - MDW
    3. Take the train from Van Buren St. to Gary Metro Centertrain train
    6h 14m
    $119–492

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

    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 26m
    $87–345

  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
    $153–295

  11. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Dyer Stationtrain train Cardinal
    27h 7m
    $289–613

Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD) flights

Calendar130Weekly Planes
Duration2h 55mAverage Duration
Ticket$46Cheapest Price
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Questions & Answers

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

Flixbus USA operates a bus from New York Midtown to Merrillville once daily. Tickets cost $110–190 and the journey takes 19h 10m. 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 27m.

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