Rome2Rio

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

Find Transport to Brattleboro

See all options

There are 9 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 Windsor Locks to Brattleboro Stationtrain train
    7h 34m
    $128–558

  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 5m
    $102–448

  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
    $321–644

  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
    $154–299

  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

    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the bus from Albany International Airport to Green Mountain Community Bus Terminalbus bus
    9h 29m
    $150–767

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Albany County Airport (ALB)plane plane ORD - ALB
    2. Take the bus from Albany International Airport to Green Mountain Community Bus Terminalbus bus
    9h 56m
    $120–617

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

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take the bus from Boston to Springfield Union Stationbus bus
    3. Take the train from Springfield to Brattleboro Stationtrain train
    9h 20m
    $136–589

  9. Bus, train

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Brattleboro Stationtrain train Vermonter
    23h 28m
    $206–359

Chicago to Brattleboro by train (Amtrak)

Calendar7Weekly Trains
Duration22hAverage Duration
Ticket$321Cheapest Price
See schedules

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 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.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers