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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 8 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
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)planeALB - MDW
    7h 35m
    $127–650

  2. Train (Amtrak)

    cheapest
    1. Take the train from Pittsfield Amtrak Station to Chicago Union StationtrainLake Shore Limited
    20h
    $76–286

  3. Bus

    1. Take the bus from Lenox to Port Authority Bus TerminalbusWilliamstown
    2. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    25h 21m
    $114–263

  4. Drive 854.4 mi

    1. Drive from Lenox to Chicagocar854.4 mi
    14h 35m
    $156–226

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

    1. Take the bus from Pittsfield to Albany Bus Terminal, NYbus
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)planeALB - ORD
    8h 8m
    $217–600

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

    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)planeBDL - MDW
    8h 49m
    $107–774

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

    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)planeBDL - ORD
    9h 7m
    $362–934

  8. Train, train to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Pittsfield Amtrak Station to Croton-Harmon Amtrak Stationtrain
    2. Take the train from Croton-Harmon to 125th Street - Harlemtrain
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)planeLGA - MDW
    10h 29m
    $110–550

Lenox to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration20hAverage Duration
Ticket$76Cheapest Price
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Questions & Answers

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 $75–260 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 25h 21m.

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