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

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There are 9 ways to get from Weston 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 58m
    $166–563

  2. Drive 833.8 mi

    cheapest
    1. Drive from Weston to Chicagocar car 833.8 mi
    14h 6m
    $153–220

  3. Bus

    1. Take the bus from Bridgeport Bus Stop to Port Authority Bus Terminalbus bus Greyhound US0255s
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    22h 12m
    $168–280

  4. Train

    1. Take the train from South Norwalk to 125th Street - Harlemtrain train
    2. Take the train from 125th Street - Harlem to Croton-Harmontrain train
    3. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train
    22h 18m
    $342–721

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

    1. Take the train from South Norwalk to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 52m
    $247–617

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

    1. Take the train from South Norwalk to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 13m
    $257–717

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

    1. Take the train from South Norwalk 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 39m
    $368–928

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

    1. Take the train from South Norwalk to Grand Central Terminaltrain train
    2. Take the bus from Bryant Park to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    7h 7m
    $189–935

  9. Train, bus

    1. Take the train from South Norwalk 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
    25h 57m
    $184–394

Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD) flights

Calendar86Weekly Planes
Duration4h 21mAverage Duration
Ticket$93Cheapest Price
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Questions & Answers

Map of how to get from Weston to Chicago.ExpandLaunch map view
  • Distance: 778 mi
  • Duration: 3h 58m

What companies run services between Weston, 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 vehicle from Weston to Chicago Bus Station via Post Rd. East at Opposite Main St., Bridgeport Bus Stop, Port Authority Bus Terminal, and New York Midtown in around 22h 12m.

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