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

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There are 7 ways to get from Lee to Chicago by bus, plane, train (Amtrak), bus (Greyhound, Flixbus), or car

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 Lee to Albany Bus Terminal, NYbus bus
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    6h 18m
    $113–573

  2. Bus to Bradley International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Lee to Springfield Union Stationbus bus
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    7h 4m
    $73–350

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 14m
    $282–602

  4. Bus

    1. Take the bus from Lee to Springfield Union Stationbus bus
    2. Take the bus from Springfield Union Station to Newark Penn Stationbus bus
    3. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus
    22h 30m
    $156–282

  5. Drive 857.8 mi

    1. Drive from Lee to Chicagocar car 857.8 mi
    14h 39m
    $157–227

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

    1. Take the bus from Lee to Albany Bus Terminal, NYbus bus
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    6h 47m
    $103–493

  7. Bus to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Lee to Springfield Union Stationbus bus
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    6h 30m
    $83–410

Lee to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration20h 14mAverage Duration
Ticket$282Cheapest Price
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Questions & Answers

Map of how to get from Lee to Chicago.ExpandLaunch map view
  • Distance: 783.4 mi
  • Duration: 6h 18m

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

Amtrak operates a train from Pittsfield Amtrak Station to Chicago Union Station once daily. Tickets cost $280–600 and the journey takes 18h 30m. Alternatively, you can take a bus from Lee to Chicago Bus Station via Springfield Union Station and Newark Penn Station in around 22h 30m.

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