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

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There are 9 ways to get from Rye to Chicago by plane, train (Amtrak), bus (Flixbus), car, train, 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 Westchester County Airport to Chicago O'Hare International Airport

    best
    1. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    3h 45m
    $135–632

  2. Train

    1. Take the train from 125th Street - Harlem to Croton-Harmontrain train Hudson
    2. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    21h 40m
    $519–831

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    24h 50m
    $159–254

  4. Drive  808.3 mi

    1. Drive from Rye to Chicagocar car 808.3 mi
    13h 32m
    $148–214

  5. Train, bus to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Rye to 125th Street - Harlemtrain train
    2. Take the bus from E 125 St/Lexington Av to Laguardia Rd/94 Stbus bus
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 18m
    $214–677

  6. Train, bus to Laguardia Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Rye to 125th Street - Harlemtrain train
    2. Take the bus from E 125 St/Lexington Av to Laguardia Rd/94 Stbus bus
    3. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 40m
    $144–577

  7. Train, train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Rye to Grand Central Terminaltrain train
    2. Take the train from Grand Central Terminal to Jamaicatrain train
    3. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 7m
    $336–888

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

    1. Take the bus from Bryant Park to Terminal Bbus bus
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 37m
    $147–795

  9. 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
    25h 27m
    $183–288

Rye to Chicago by train

Calendar7Weekly Trains
Duration21h 40mAverage Duration
Ticket$519Cheapest Price
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Comparing Your Travel Options

Map of how to get from Rye to Chicago.ExpandLaunch map view
  • Distance: 762 mi
  • Duration: 3h 45m

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

American Airlines and Delta fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, you can take a train from Rye to Chicago Union Station via 125th Street - Harlem and Croton-Harmon Amtrak Station in around 21h 40m.

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