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

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There are 7 ways to get from Chicago Midway Airport (MDW) 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
    6h
    $120–548

  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 37m
    $102–473

  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
    23h 26m
    $284–624

  4. Bus

    1. Take the bus from Chicago to New York Midtownbus bus
    2. Take the bus from New York Midtown to Springfield Union Stationbus bus
    3. Take the bus from Springfield Union Station to Brattleborobus bus
    28h 22m
    $174–296

  5. 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
    7h 36m
    $166–771

  6. 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
    8h 54m
    $152–593

  7. Drive 883.3 mi

    1. Drive from Chicago Midway Airport (MDW) to Brattleborocar car 883.3 mi
    15h 53m
    $162–233

Chicago Midway Airport (MDW) to Brattleboro by subway, bus, and train

Calendar7Weekly Services
Duration23h 26mAverage Duration
Ticket$284Cheapest Price
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Questions & Answers

Map of how to get from Chicago Midway Airport (MDW) to Brattleboro.ExpandLaunch map view
  • Distance: 853.7 mi
  • Duration: 6h

What companies run services between Chicago Midway Airport (MDW), USA and Brattleboro, VT, USA?

You can take a bus from Midway Orange Line Station to Brattleboro via Ashland & 59th Street, 95th Red Line Station, Chicago, New York Midtown, and Springfield Union Station in around 28h 22m.

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