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

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There are 9 ways to get from Greenwich to Chicago by plane, bus (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
    $108–469

  2. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    20h 55m
    $136–240

  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 2m
    $323–674

  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 21m
    $165–578

  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 42m
    $215–678

  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 10m
    $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 36m
    $187–1,446

  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 44m
    $168–374

Greenwich to Chicago by bus (Flixbus)

Calendar7Weekly Buses
Duration20h 55mAverage Duration
Ticket$136Cheapest 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) hourly. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $130–230 and the journey takes 16h 55m.

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