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How to get fromGreenwich to Chicagoby plane, bus (Greyhound, Flixbus), train (Amtrak), car, train, or bus

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There are 9 ways to get from Greenwich to Chicago by plane, bus (Greyhound, Flixbus), 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 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 33m
    $118–579

  2. Bus

    1. Take the bus from Stamford Bus Stop to Port Authority Bus Terminalbus bus Greyhound US0240
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    21h 17m
    $137–235

  3. Train

    1. Take the train from Greenwich to Grand Central Terminaltrain train New Haven / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    22h 1m
    $303–674

  4. Drive 813.1 mi

    1. Drive from Greenwich to Chicagocar car 813.1 mi
    13h 36m
    $149–215

  5. Train, bus to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Greenwich 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 19m
    $215–578

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

    1. Take the train from Greenwich 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 40m
    $145–678

  7. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Greenwich to Grand Central Terminaltrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 9m
    $336–889

  8. Train, bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Greenwich to Grand Central Terminaltrain train
    2. Take the bus from Grand Central to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 35m
    $157–896

  9. Train, bus

    1. Take the train from Greenwich to Grand Central Terminaltrain train
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    24h 43m
    $168–354

Greenwich to Chicago by bus and foot

Calendar7Weekly Services
Duration21h 17mAverage Duration
Ticket$137Cheapest Price
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Questions & Answers

Map of how to get from Greenwich to Chicago.ExpandLaunch map view
  • Distance: 761.1 mi
  • Duration: 3h 33m

What companies run services between Greenwich, CT, 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, you can take a bus from Mason St @ Lexington Ave to Chicago Bus Station via Stamford Transportation Center @ Bay E, Stamford Bus Stop, Port Authority Bus Terminal, and New York Midtown in around 21h 17m.

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