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

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There are 10 ways to get from Times Square to Chicago by plane, bus (Flixbus), train (Amtrak), 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
    $127–665

  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
    6h 52m
    $90–433

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    16h 55m
    $120–220

  4. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    19h 32m
    $310–650

  5. Drive 790 mi

    1. Drive from Times Square to Chicagocar car 790 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 6m
    $117–480

  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 22m
    $97–345

  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 4m
    $446–873

  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 42m
    $126–1,204

  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
    22h 55m
    $155–333

Times Square to Chicago by bus (Flixbus)

Calendar15Weekly Buses
Duration16h 55mAverage Duration
Ticket$120Cheapest Price
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Questions & Answers

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 and Delta fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) every 3 hours. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $120–220 and the journey takes 16h 55m.

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