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

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There are 8 ways to get from Chicago to Brattleboro by plane, train, bus, bus (Flixbus, Greyhound), 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. Fly Chicago Midway International Airport to Bradley International Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Windsor Locks to Brattleboro Stationtrain train
    7h 34m
    $134–658

  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 Windsor Locks to Brattleboro Stationtrain train
    8h 6m
    $110–498

  3. Train, bus

    1. Take the train from Chicago Union Station to Springfieldtrain train Lake Shore Limited
    2. Take the bus from Springfield Union Station to Brattleborobus bus Greyhound US0255s
    21h 39m
    $270–583

  4. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus
    2. Take the bus from Newark Penn Station to Springfield Union Stationbus bus
    3. Take the bus from Springfield Union Station to Brattleborobus bus
    23h 15m
    $154–261

  5. Drive 882.5 mi

    1. Drive from Chicago to Brattleborocar car 882.5 mi
    15h 48m
    $162–233

  6. Fly Chicago Midway International Airport to Albany County Airport, bus, train

    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 Northamptonbus bus
    3. Take the train from Northampton to Brattleboro Stationtrain train
    9h 11m
    $168–854

  7. Fly Chicago O'Hare International Airport to Albany County Airport, bus, train

    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 Northamptonbus bus
    3. Take the train from Northampton to Brattleboro Stationtrain train
    9h 37m
    $138–654

  8. Fly Chicago Midway International Airport to Boston Logan Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take the train from Boston to Springfieldtrain train
    3. Take the train from Springfield to Brattleboro Stationtrain train
    10h 29m
    $156–664

Chicago to Brattleboro by train and bus

Calendar7Weekly Services
Duration21h 39mAverage Duration
Ticket$270Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Brattleboro.ExpandLaunch map view
  • Distance: 864.8 mi
  • Duration: 7h 34m

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

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

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