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

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There are 9 ways to get from Great Barrington 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 Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Great Barrington to New Yorkbus bus
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 41m
    $232–710

  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 47m
    $87–407

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 20m
    $232–552

  4. Bus

    1. Take the bus from Great Barrington 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
    21h 17m
    $144–282

  5. Drive 859 mi

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

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

    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
    8h 6m
    $119–633

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

    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 36m
    $109–523

  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
    8h 13m
    $97–467

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

    1. Take the bus from Great Barrington to New Yorkbus bus
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    10h 9m
    $144–633

Great Barrington to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration20h 20mAverage Duration
Ticket$232Cheapest Price
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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 $230–550 and the journey takes 18h 30m. Alternatively, you can take a bus from Great Barrington to Chicago Bus Station via New York, Port Authority Bus Terminal, and Newark Penn Station in around 21h 17m.

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