Rome2Rio

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

Find Transport to Chicago

See all options

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

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 Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Great Barrington to Port Authority Bus Terminalbus bus
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 41m
    $211–622

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

    cheapest
    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    9h 28m
    $91–375

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 20m
    $282–602

  4. Bus

    1. Take the bus from Great Barrington to Port Authority Bus Terminalbus bus Williamstown
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    21h 11m
    $166–304

  5. Drive 859 mi

    1. Drive from Great Barrington to Chicagocar car 859 mi
    14h 48m
    $157–227

  6. Line 921 bus, bus, line 905 bus to Albany County Airport, fly to Chicago Midway International Airport

    1. Take the bus from Great Barrington Fire Department to Intermodal Centerbus bus
    2. Take the bus from Pittsfield to Albany Bus Terminal, NYbus bus
    3. Take the bus from Albany Bus Terminal to Colonie Station - Central Ave & Colonie Centerbus bus
    4. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    7h 43m
    $123–572

  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 12m
    $103–492

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

    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    8h 54m
    $101–435

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

    1. Take the bus from Great Barrington 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 17m
    $133–545

Great Barrington to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration20h 20mAverage Duration
Ticket$282Cheapest Price
See schedules

Questions & Answers

Map of how to get from Great Barrington to Chicago.ExpandLaunch map view
  • Distance: 861.2 mi
  • Duration: 7h 41m

What companies run services between Great Barrington, 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 Great Barrington to Chicago Bus Station via Port Authority Bus Terminal and New York Midtown in around 21h 11m.

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

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers