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

Find Transport to Stockbridge

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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 Bus Terminal, NY to Pittsfieldbus bus
    8h 12m
    $166–828

  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 55m
    $112–517

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Pittsfield Amtrak Stationtrain train Lake Shore Limited
    19h 35m
    $481–739

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640 / ...
    2. Take the bus from New York to Stockbridgebus bus Bz 0712
    24h 58m
    $180–279

  5. Drive  853.8 mi

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

  6. 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 New York to Stockbridgebus bus
    8h 51m
    $230–703

  7. 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 Bus Terminal, NY to Pittsfieldbus bus
    8h 46m
    $116–578

  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
    $152–737

  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 25m
    $118–481

Chicago to Stockbridge by train and bus (Amtrak)

Calendar7Weekly Services
Duration19h 35mAverage Duration
Ticket$481Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Stockbridge.ExpandLaunch map view
  • Distance: 788.5 mi
  • Duration: 8h 12m

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 $470–750 and the journey takes 18h. Alternatively, you can take a bus from Chicago Bus Station to Stockbridge via New York Midtown, 8 Av/W 31 St, 8 Av/W 41 St, and New York in around 24h 58m.

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