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

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There are 10 ways to get from Freeport to Chicago by plane, bus (Flixbus), train (Amtrak), car, 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 John F. Kennedy International Airport to Chicago O'Hare International Airport

    best
    1. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    5h 2m
    $327–874

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

    cheapest
    1. Take the train from Freeport to Grand Central Terminaltrain train
    2. Take the train from Grand Central Terminal to White Plainstrain train
    3. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 42m
    $112–509

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    18h 39m
    $148–256

  4. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    21h 16m
    $308–666

  5. Drive 811.6 mi

    1. Drive from Freeport to Chicagocar car 811.6 mi
    13h 46m
    $149–214

  6. Fly Laguardia Airport to Chicago Midway International Airport

    1. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 10m
    $213–579

  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 31m
    $223–679

  8. Train, train to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Freeport to New York Penn Stationtrain train
    2. Take the train from New York Penn Station to Newark Airport Railroad Stationtrain train
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    5h 49m
    $150–899

  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
    6h 40m
    $173–994

  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
    24h 27m
    $163–366

Freeport to Chicago by train and bus (Flixbus)

Calendar15Weekly Services
Duration18h 39mAverage Duration
Ticket$148Cheapest Price
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Questions & Answers

Map of how to get from Freeport to Chicago.ExpandLaunch map view
  • Distance: 773.9 mi
  • Duration: 5h 2m

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

American Airlines, JetBlue Airways, and Delta fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $140–240 and the journey takes 16h 55m.

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