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How to get fromChicago to Old Greenwichby plane, train (Amtrak), bus (Flixbus, Greyhound), car, train, or bus

Find Transport to Old Greenwich

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

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 15m
    $118–505

  2. Train

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train
    2. Take the train from Croton-Harmon to 125th Street - Harlemtrain train
    3. Take the train from 125th Street - Harlem to Old Greenwichtrain train
    21h 45m
    $248–572

  3. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640 / ...
    2. Take the bus from Port Authority Bus Terminal to Stamford Bus Stopbus bus Greyhound US0240
    23h 17m
    $158–238

  4. Drive  818 mi

    1. Drive from Chicago to Old Greenwichcar car 818 mi
    13h 47m
    $150–216

  5. 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 Old Greenwichtrain train
    5h 44m
    $146–579

  6. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Old Greenwichtrain train
    5h 30m
    $216–679

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

    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 Grand Central Terminal to Old Greenwichtrain train
    6h 4m
    $338–890

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Stationtrain train
    6h 25m
    $156–1,442

  9. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to New Yorkbus bus
    3. Take the train from Grand Central Terminal to Old Greenwichtrain train
    23h 54m
    $179–296

Chicago to Old Greenwich by train

Calendar7Weekly Trains
Duration21h 45mAverage Duration
Ticket$248Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Old Greenwich.ExpandLaunch map view
  • Distance: 765.4 mi
  • Duration: 4h 15m

What companies run services between Chicago, IL, USA and Old Greenwich, CT, USA?

American Airlines and Delta fly 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 Old Greenwich via Croton-Harmon and 125th Street - Harlem in around 21h 45m.

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