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

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There are 7 ways to get from Brattleboro to Chicago by train, plane, bus, 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. Train to Bradley International Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Brattleboro Station to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    6h 34m
    $104–464

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

    cheapest
    1. Take the train from Brattleboro Station to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    7h 8m
    $94–414

  3. Bus, train

    1. Take the bus from Brattleboro to Springfield Union Stationbus bus Greyhound US0255s
    2. Take the train from Springfield to Chicago Union Stationtrain train Lake Shore Limited
    22h 16m
    $258–615

  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
    23h 15m
    $146–260

  5. Drive 883 mi

    1. Drive from Brattleboro to Chicagocar car 883 mi
    15h 48m
    $162–233

  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 35m
    $128–653

  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 5m
    $123–553

Brattleboro to Chicago by bus and train

Calendar7Weekly Services
Duration22h 16mAverage Duration
Ticket$258Cheapest Price
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Questions & Answers

Map of how to get from Brattleboro to Chicago.ExpandLaunch map view
  • Distance: 863.9 mi
  • Duration: 6h 34m

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

You can take a bus from Brattleboro to Chicago Bus Station via Springfield Union Station and Newark Penn Station in around 23h 15m.

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