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How to get fromChicago to Ryeby plane, train (Amtrak), bus (Greyhound), car, subway, train, shuttle, or bus (Flixbus)

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There are 9 ways to get from Chicago to Rye by plane, train (Amtrak), bus (Greyhound), car, subway, train, shuttle, or bus (Flixbus)

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 Chicago O'Hare International Airport to Westchester County Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    4h 18m
    $114–492

  2. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Jamaica to Grand Central Terminaltrain train
    3. Take the train from Grand Central Terminal to Ryetrain train
    5h 48m
    $80–338

  3. Train

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    2. Take the train from Croton-Harmon to 125th Street - Harlemtrain train Hudson
    21h 26m
    $306–615

  4. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus Greyhound US0164
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus Greyhound US0670 / ...
    22h 56m
    $169–363

  5. Drive 808.2 mi

    1. Drive from Chicago to Ryecar car 808.2 mi
    13h 32m
    $148–213

  6. Subway to Chicago Midway International Airport, fly to Laguardia Airport, train

    1. Take the subway from Adams/Wabash to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    3. Take the train from 125th Street - Harlem to Ryetrain train
    5h 14m
    $144–726

  7. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Ryetrain train
    5h 35m
    $104–286

  8. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, shuttle

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take a shuttle bus from Newark Airport Terminal B to Grand Centralshuttle bus
    6h 26m
    $146–360

  9. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2642 / ...
    26h 17m
    $152–247

Chicago to Rye by train

Calendar7Weekly Trains
Duration21h 26mAverage Duration
Ticket$306Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Rye.ExpandLaunch map view
  • Distance: 762 mi
  • Duration: 4h 18m

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

American Airlines flies from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN) every 4 hours. Alternatively, you can take a train from Chicago Union Station to Rye via Croton-Harmon and 125th Street - Harlem in around 21h 26m.

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