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

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There are 9 ways to get from Chicago to Stockbridge by plane, bus, train (Amtrak), bus (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. Fly Chicago Midway International Airport to Albany County Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the bus from Albany to Leebus bus
    8h 8m

  2. Fly Chicago O'Hare International Airport to Bradley International Airport, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the bus from Springfield to Leebus bus
    8h 57m
    $92–433

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Pittsfield Amtrak Stationtrain train Lake Shore Limited
    19h 35m
    $285–573

  4. 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 Stockbridgebus bus New York
    21h 41m
    $172–305

  5. Drive 853.8 mi

    1. Drive from Chicago to Stockbridgecar car 853.8 mi
    14h 39m
    $156–226

  6. Fly Chicago O'Hare International Airport to Albany County Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Albany County Airport (ALB)plane plane ORD - ALB
    2. Take the bus from Albany to Leebus bus
    8h 35m

  7. Fly Chicago Midway International Airport to Laguardia Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the bus from Port Authority Bus Terminal to Stockbridgebus bus
    8h 46m
    $212–628

  8. Fly Chicago Midway International Airport to Bradley International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the bus from Springfield to Leebus bus
    8h 26m
    $116–543

  9. Fly Chicago O'Hare International Airport to Westchester County Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from New York to Stockbridgebus bus
    11h 18m

Chicago to Stockbridge by train and bus (Amtrak)

Calendar7Weekly Services
Duration19h 35mAverage Duration
Ticket$285Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Stockbridge.ExpandLaunch map view
  • Distance: 790.9 mi
  • Duration: 8h 8m

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

Amtrak operates a train from Chicago Union Station to Pittsfield Amtrak Station once daily. Tickets cost $280–600 and the journey takes 18h. Alternatively, you can take a bus from Chicago Bus Station to Stockbridge via New York Midtown and Port Authority Bus Terminal in around 21h 41m.

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