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

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There are 8 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)plane plane MDW - ALB
    2. Take the bus from Albany Bus Terminal, NY to Pittsfieldbus bus
    7h 38m
    $152–824

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the train from Springfield to Pittsfield Amtrak Stationtrain train
    9h 28m
    $104–476

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Pittsfield Amtrak Stationtrain train Lake Shore Limited
    19h 9m
    $255–533

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640 / ...
    2. Take the bus from Port Authority Bus Terminal to Lenoxbus bus New York
    25h 11m
    $156–276

  5. Drive 853.9 mi

    1. Drive from Chicago to Lenoxcar car 853.9 mi
    14h 44m
    $156–226

  6. 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 Bus Terminal, NY to Pittsfieldbus bus
    8h 8m
    $112–574

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

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Springfield to Pittsfield Amtrak Stationtrain train
    8h 57m
    $134–656

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

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Pittsfield Amtrak Stationtrain train
    10h 27m
    $192–835

Chicago to Lenox by train and bus (Amtrak)

Calendar7Weekly Services
Duration19h 9mAverage Duration
Ticket$255Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Lenox.ExpandLaunch map view
  • Distance: 781 mi
  • Duration: 7h 38m

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 $250–550 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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