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

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There are 8 ways to get from Chicago to Lenox by plane, bus, train (Amtrak), bus (Flixbus, Greyhound), 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 to Lenoxbus bus
    6h 43m
    $146–781

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the bus from Springfield to Lenoxbus bus
    8h 2m
    $92–452

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Pittsfield Amtrak Stationtrain train Lake Shore Limited
    19h 6m
    $268–567

  4. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus
    2. Take the bus from Newark Penn Station to Port Authority Bus Terminalbus bus 108
    3. Take the bus from Port Authority Bus Terminal to Lenoxbus bus
    22h
    $163–316

  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 to Lenoxbus bus
    7h 10m
    $126–631

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

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the bus from Springfield to Lenoxbus bus
    7h 31m
    $112–542

  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 24m
    $262–695

Chicago to Lenox by train and bus (Amtrak)

Calendar7Weekly Services
Duration19h 6mAverage Duration
Ticket$268Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Lenox.ExpandLaunch map view
  • Distance: 780.1 mi
  • Duration: 6h 43m

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 $260–600 and the journey takes 18h. Alternatively, you can take a bus from Chicago Bus Station to Lenox via Newark Penn Station and Port Authority Bus Terminal in around 22h.

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