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

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There are 9 ways to get from Stockbridge to Chicago by bus, plane, train (Amtrak), bus (Greyhound, Flixbus), or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Bus to Albany County Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Pittsfield to Albany Bus Terminal, NYbus bus
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    7h 39m
    $135–677

  2. Bus to Bradley International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Lee to Springfieldbus bus
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    8h 21m
    $86–396

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 2m
    $473–755

  4. Bus

    1. Take the bus from Stockbridge to New Yorkbus bus
    2. Take the bus from Port Authority Bus Terminal to Newark Penn Stationbus bus 108
    3. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus
    24h 52m
    $173–303

  5. Drive  853.5 mi

    1. Drive from Stockbridge to Chicagocar car 853.5 mi
    14h 38m
    $156–225

  6. Bus to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the bus from Stockbridge to New Yorkbus bus
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    8h 1m
    $230–701

  7. Bus to Albany County Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Pittsfield to Albany Bus Terminal, NYbus bus
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    8h 17m
    $105–517

  8. Bus to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Lee to Springfieldbus bus
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    7h 48m
    $111–516

  9. Bus to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Stockbridge to New Yorkbus bus
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    10h 38m
    $152–674

Stockbridge to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration20h 2mAverage Duration
Ticket$473Cheapest Price
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Comparing Your Travel Options

Map of how to get from Stockbridge to Chicago.ExpandLaunch map view
  • Distance: 788 mi
  • Duration: 7h 39m

What companies run services between Stockbridge, MA, USA and Chicago, IL, USA?

Amtrak operates a train from Pittsfield Amtrak Station to Chicago Union Station once daily. Tickets cost $470–750 and the journey takes 18h 30m. Alternatively, you can take a bus from Stockbridge to Chicago Bus Station via New York, Port Authority Bus Terminal, and Newark Penn Station in around 24h 52m.

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Want to know more about travelling around United States

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