Rome2Rio

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

Find Transport to Chicago

See all options

There are 8 ways to get from Stockbridge to Chicago by bus, plane, 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. Bus to Albany County Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Lee to Albanybus bus
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    7h 36m
    $127–589

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

    cheapest
    1. Take the bus from Lee to Albanybus bus
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    8h 5m
    $107–509

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 2m
    $283–608

  4. Bus

    1. Take the bus from Stockbridge to Port Authority Bus Terminalbus bus Williamstown
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    21h 26m
    $167–307

  5. Drive 853.5 mi

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

  6. 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 43m

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

    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 17m

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

    1. Take the bus from Stockbridge to Port Authority Bus Terminalbus bus
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    10h 32m
    $134–548

Stockbridge to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration20h 2mAverage Duration
Ticket$283Cheapest Price
See schedules

Questions & Answers

Map of how to get from Stockbridge to Chicago.ExpandLaunch map view
  • Distance: 790.3 mi
  • Duration: 7h 36m

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 $280–600 and the journey takes 18h 30m. Alternatively, you can take a bus from Stockbridge to Chicago Bus Station via Port Authority Bus Terminal and New York Midtown in around 21h 26m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

More Questions & Answers