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

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There are 9 ways to get from Chicago to Old Greenwich by plane, bus (Flixbus, Greyhound), train (Amtrak), 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 23m
    $132–545

  2. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from Port Authority Bus Terminal to Stamford Bus Stopbus bus Greyhound US0240
    20h 12m
    $221–306

  3. 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
    $321–636

  4. Drive 818 mi

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

  5. 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 31m
    $196–579

  6. 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 51m
    $226–679

  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 27m
    $196–1,442

  9. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to Old Greenwichtrain train
    23h 19m
    $180–383

Chicago to Old Greenwich by bus, foot, and train

Calendar14Weekly Services
Duration20h 12mAverage Duration
Ticket$221Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Old Greenwich.ExpandLaunch map view
  • Distance: 765.4 mi
  • Duration: 4h 23m

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 bus from Chicago Bus Station to Old Greenwich via New York Midtown, Port Authority Bus Terminal, Stamford Bus Stop, and Stamford in around 20h 12m.

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