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

Find Transport to Chicago

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There are 5 ways to get from Bennington to Chicago by bus, plane, train, bus (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. Bus, fly to Chicago Midway International Airport

    best
    1. Take the bus from Green Mountain Community Bus Terminal to Albany International Airportbus bus
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    5h 36m
    $111–616

  2. Bus, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Green Mountain Community Bus Terminal to Albany International Airportbus bus
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    6h 5m
    $96–486

  3. Bus, train

    1. Take the bus from Green Mountain Community Bus Terminal to AMTRAK Station Rensselaerbus bus 7
    2. Take the train from Albany-Rensselaer Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    18h 12m
    $227–609

  4. Bus

    1. Take the bus from Green Mountain Community Bus Terminal to Greyhound \ Trailways Terminalbus bus 7
    2. Take the bus from Albany Bus Terminal, NY to Cleveland Bus Stationbus bus
    3. Take the bus from Cleveland Bus Station to Chicago Bus Stationbus bus
    20h 55m
    $142–229

  5. Drive  843 mi

    1. Drive from Bennington to Chicagocar car 843 mi
    14h 45m
    $154–223

Bennington to Chicago by bus and train

Calendar14Weekly Services
Duration18h 12mAverage Duration
Ticket$227Cheapest Price
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Comparing Your Travel Options

Map of how to get from Bennington to Chicago.ExpandLaunch map view
  • Distance: 775.6 mi
  • Duration: 5h 36m

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

You can take a bus from Green Mountain Community Bus Terminal to Chicago Bus Station via Albany Bus Terminal, NY and Cleveland Bus Station in around 20h 55m.

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Need to know: Greyhound

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