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

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There are 8 ways to get from Brattleboro to Chicago by train, plane, train (Amtrak), bus (Greyhound, Flixbus), car, or bus

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

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

    best
    1. Take the train from Brattleboro Station to Hartford Amtrak Stationtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    7h 28m
    $141–569

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

    cheapest
    1. Take the train from Brattleboro Station to Hartford Amtrak Stationtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    7h 57m
    $116–429

  3. Train (Amtrak)

    1. Take the train from Brattleboro Station to Springfieldtrain train Vermonter
    2. Take the train from Springfield to Chicago Union Stationtrain train Lake Shore Limited
    22h 19m
    $533–851

  4. Bus

    1. Take the bus from Brattleboro 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
    26h 35m
    $191–296

  5. Drive  883 mi

    1. Drive from Brattleboro to Chicagocar car 883 mi
    15h 47m
    $156–226

  6. Train, bus to Albany County Airport, fly to Chicago Midway International Airport

    1. Take the train from Brattleboro Station to Northamptontrain train
    2. Take the bus from Northampton to Albany Bus Terminal, NYbus bus
    3. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    8h 59m
    $172–764

  7. Train, bus to Albany County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Brattleboro Station to Northamptontrain train
    2. Take the bus from Northampton to Albany Bus Terminal, NYbus bus
    3. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    9h 27m
    $132–564

  8. Train, train to Boston Logan Airport, fly to Chicago Midway International Airport

    1. Take the train from Brattleboro Station to Springfieldtrain train
    2. Take the train from Springfield to Bostontrain train
    3. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    10h 3m
    $194–700

Brattleboro to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration22h 19mAverage Duration
Ticket$533Cheapest Price
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Comparing Your Travel Options

Map of how to get from Brattleboro to Chicago.ExpandLaunch map view
  • Distance: 884.8 mi
  • Duration: 7h 28m

What companies run services between Brattleboro, VT, USA and Chicago, IL, USA?

You can take a train from Brattleboro Station to Chicago Union Station via Springfield in around 22h 19m. Alternatively, you can take a bus from Brattleboro to Chicago Bus Station via Springfield Union Station and Newark Penn Station in around 26h 35m.

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