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How to get fromChicago to Lenoxby plane, bus, train (Amtrak), bus (Flixbus), car or train

Find Transport to Lenox

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There are 9 ways to get from Chicago to Lenox by plane, bus, 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. Fly Chicago Midway International Airport to Albany County Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)planeMDW - ALB
    2. Take the bus from Albany Bus Terminal, NY to Pittsfieldbus
    7h 41m
    $138–753

  2. Train (Amtrak)

    cheapest
    1. Take the train from Chicago Union Station to Pittsfield Amtrak StationtrainLake Shore Limited
    19h 9m
    $81–282

  3. Bus

    1. Take the bus from Chicago Bus Station to New York MidtownbusFlixBus N2640
    2. Take the bus from Port Authority Bus Terminal to LenoxbusNew York
    25h 11m
    $121–330

  4. Drive 854.5 mi

    1. Drive from Chicago to Lenoxcar854.5 mi
    14h 35m
    $156–226

  5. 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)planeORD - ALB
    2. Take the bus from Albany Bus Terminal, NY to Pittsfieldbus
    8h 12m
    $218–603

  6. Fly Chicago Midway International Airport to Bradley International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)planeMDW - BDL
    2. Take the train from Springfield to Pittsfield Amtrak Stationtrain
    8h 54m
    $126–944

  7. Fly Chicago O'Hare International Airport to Bradley International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)planeORD - BDL
    2. Take the train from Springfield to Pittsfield Amtrak Stationtrain
    9h 28m
    $386–1,044

  8. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)planeMDW - LGA
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Pittsfield Amtrak Stationtrain
    10h 15m
    $132–527

  9. Fly Chicago O'Hare International Airport to Syracuse Hancock International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Syracuse Hancock International Airport (SYR)planeORD - SYR
    2. Take the train from Syracuse Regional Transportation Center to Pittsfield Amtrak Stationtrain
    11h 44m
    $132–753

Chicago to Lenox by train and bus (Amtrak)

Calendar7Weekly Services
Duration19h 9mAverage Duration
Ticket$81Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Chicago Union Station to Pittsfield Amtrak Station once daily. Tickets cost $75–260 and the journey takes 18h. Alternatively, you can take a bus from Chicago Bus Station to Lenox via New York Midtown and Port Authority Bus Terminal in around 25h 11m.

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