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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 35m
    $115–502

  2. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    21h 18m
    $149–254

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    21h 55m
    $313–673

  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 14m
    $214–577

  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 35m
    $224–677

  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
    5h 59m
    $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 30m
    $157–895

  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 27m
    $168–373

Rye to Chicago by bus and foot (Flixbus)

Calendar30Weekly Services
Duration21h 18mAverage Duration
Ticket$149Cheapest Price
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Questions & Answers

Map of how to get from Rye to Chicago.ExpandLaunch map view
  • Distance: 762 mi
  • Duration: 3h 35m

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 4 times a day. Tickets cost $140–240 and the journey takes 16h 55m.

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