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

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There are 10 ways to get from Chicago to Weston 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 42m
    $168–595

  2. Drive 833.8 mi

    cheapest
    1. Drive from Chicago to Westoncar car 833.8 mi
    14h 9m
    $153–220

  3. 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 Bridgeport Bus Stopbus bus Greyhound US0255s
    21h 21m
    $171–278

  4. 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 South Norwalktrain train
    22h 3m
    $350–680

  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 South Norwalktrain train
    5h 49m
    $246–617

  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 South Norwalktrain train
    6h 9m
    $256–717

  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 South Norwalktrain train
    6h 19m
    $368–928

  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 55m
    $186–1,479

  9. Fly Chicago Midway International Airport to Bradley International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    7h 20m
    $166–607

  10. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to South Norwalktrain train
    24h 21m
    $189–393

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

Calendar55Weekly Planes
Duration3h 12mAverage Duration
Ticket$99Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Weston.ExpandLaunch map view
  • Distance: 778.1 mi
  • Duration: 4h 42m

What companies run services between Chicago, IL, USA and Weston, 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 Weston via New York Midtown, Port Authority Bus Terminal, Bridgeport Transportation Center, and Post Rd. East at Compo Rd. North in around 21h 21m.

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