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

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There are 10 ways to get from Times Square to Chicago by plane, train (Amtrak), bus (Flixbus), car, bus, 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. Fly Laguardia Airport to Chicago Midway International Airport

    best
    1. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 6m
    $208–666

  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
    $124–622

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    19h 32m
    $500–850

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    20h 25m
    $150–240

  5. Drive  790.2 mi

    1. Drive from Times Square to Chicagocar car 790.2 mi
    13h 9m
    $145–209

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

    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 11m
    $137–820

  7. Fly Laguardia Airport to Chicago O'Hare International Airport

    1. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 28m
    $138–566

  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 7m
    $326–873

  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
    5h 48m
    $175–975

  10. 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 Chicago Bus Stationbus bus Greyhound US0164
    23h 20m
    $172–263

Times Square to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration19h 32mAverage Duration
Ticket$500Cheapest Price
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Comparing Your Travel Options

Map of how to get from Times Square to Chicago.ExpandLaunch map view
  • Distance: 747.9 mi
  • Duration: 5h 6m

What companies run services between Times Square, NY, USA and Chicago, IL, USA?

Southwest Airlines flies from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) every 3 hours. Alternatively, 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.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

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