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

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There are 7 ways to get from Lenox 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 Albany County Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Pittsfield to Albany Bus Terminal, NYbus bus
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    7h 28m
    $123–673

  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 8m
    $80–357

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h
    $272–554

  4. Bus

    1. Take the bus from Lenox to Port Authority Bus Terminalbus bus Williamstown
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2642 / ...
    27h 21m
    $170–319

  5. Drive 853.6 mi

    1. Drive from Lenox to Chicagocar car 853.6 mi
    14h 44m
    $156–225

  6. 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
    7h 58m
    $98–483

  7. 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 39m
    $100–457

Lenox to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration20hAverage Duration
Ticket$272Cheapest Price
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Questions & Answers

Map of how to get from Lenox to Chicago.ExpandLaunch map view
  • Distance: 780.6 mi
  • Duration: 7h 28m

What companies run services between Lenox, MA, USA and Chicago, IL, USA?

Amtrak operates a train from Pittsfield Amtrak Station to Chicago Union Station once daily. Tickets cost $270–550 and the journey takes 18h 30m. Alternatively, you can take a bus from Lenox to Chicago Bus Station via Port Authority Bus Terminal and New York Midtown in around 27h 21m.

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