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How to get fromChicago to Great Barringtonby plane, bus, train (Amtrak), bus (Flixbus), car, subway, or train

Find Transport to Great Barrington

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There are 9 ways to get from Chicago to Great Barrington by plane, bus, train (Amtrak), bus (Flixbus), car, subway, 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. Fly Chicago Midway International Airport to Laguardia Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the bus from New York to Great Barringtonbus bus
    8h 31m
    $228–703

  2. Fly Chicago O'Hare International Airport to Bradley International Airport, train, bus, line 21 bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the train from Windsor Locks to Springfieldtrain train
    3. Take the bus from Springfield to Leebus bus
    4. Take the bus from Lee Premium Outlets to Railroad St Southbus bus
    9h 25m
    $112–517

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Pittsfield Amtrak Stationtrain train Lake Shore Limited
    19h 52m
    $480–735

  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 Great Barringtonbus bus Bz 0712
    24h 38m
    $184–285

  5. Drive  859.2 mi

    1. Drive from Chicago to Great Barringtoncar car 859.2 mi
    14h 48m
    $157–227

  6. Fly Chicago Midway International Airport to Albany County Airport, bus

    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 47m
    $168–828

  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 to Leebus bus
    9h 21m
    $118–578

  8. Subway to Chicago Midway International Airport, fly to Bradley International Airport, train, bus, line 21 bus

    1. Take the subway from Adams/Wabash to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    3. Take the train from Windsor Locks to Springfieldtrain train
    4. Take the bus from Springfield to Leebus bus
    5. Take the bus from Lee Premium Outlets to Railroad St Southbus bus
    8h 56m
    $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 Great Barringtonbus bus
    11h 5m
    $116–481

Chicago to Great Barrington by train and bus (Amtrak)

Calendar7Weekly Services
Duration19h 52mAverage Duration
Ticket$480Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Great Barrington.ExpandLaunch map view
  • Distance: 860.8 mi
  • Duration: 8h 31m

What companies run services between Chicago, IL, USA and Great Barrington, 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 Great Barrington via New York Midtown, 8 Av/W 31 St, 8 Av/W 41 St, and New York in around 24h 38m.

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