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

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There are 9 ways to get from Rye to Chicago by plane, bus (Flixbus), train (Amtrak), 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 39m
    $465–632

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

    cheapest
    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 34m
    $78–316

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    20h 51m
    $122–219

  4. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    21h 54m
    $272–622

  5. Drive 808.3 mi

    1. Drive from Rye to Chicagocar car 808.3 mi
    13h 33m
    $148–214

  6. 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 20m
    $93–486

  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 2m
    $526–1,238

  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 30m
    $112–335

  9. 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 36m
    $177–352

Rye to Chicago by train and bus (Flixbus)

Calendar14Weekly Services
Duration20h 51mAverage Duration
Ticket$122Cheapest Price
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Questions & Answers

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) every 2 hours. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $110–200 and the journey takes 16h 55m.

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