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

Find Transport to Brattleboro

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There are 10 ways to get from Chicago to Brattleboro by plane, train, train (Amtrak), bus (Greyhound), 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. 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 Hartford Amtrak Station to Brattleboro Stationtrain train
    8h 7m
    $200–932

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

    cheapest
    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 51m
    $142–617

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Springfieldtrain train Lake Shore Limited
    2. Take the train from Springfield to Brattleboro Stationtrain train Vermonter
    22h
    $536–831

  4. Bus (Greyhound)

    1. Take the bus from Chicago Bus Station to Cleveland Bus Stationbus bus
    2. Take the bus from Cleveland Bus Station to Springfield Union Stationbus bus
    3. Take the bus from Springfield Union Station to Brattleborobus bus
    22h 25m
    $174–270

  5. Drive  882.5 mi

    1. Drive from Chicago to Brattleborocar car 882.5 mi
    15h 48m
    $156–226

  6. Fly Chicago O'Hare International Airport to Bradley International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the train from Hartford Amtrak Station to Brattleboro Stationtrain train
    8h 32m
    $144–582

  7. 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 19m
    $202–967

  8. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to New Haventrain train
    3. Take the train from New Haven to Brattleboro Stationtrain train
    10h 48m
    $298–801

  9. 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 24m
    $212–804

  10. Bus, train

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640 / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Brattleboro Stationtrain train Vermonter
    26h 33m
    $260–404

Chicago to Brattleboro by train (Amtrak)

Calendar7Weekly Trains
Duration22hAverage Duration
Ticket$536Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Brattleboro.ExpandLaunch map view
  • Distance: 884.8 mi
  • Duration: 8h 7m

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

You can take a train from Chicago Union Station to Brattleboro Station via Springfield in around 22h. Alternatively, you can take a bus from Chicago Bus Station to Brattleboro via Cleveland Bus Station and Springfield Union Station in around 22h 25m.

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