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

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There are 6 ways to get from Chicago to Bennington by plane, bus, train, bus (Greyhound), car, or bus (Flixbus)

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 from Chicago Midway International Airport, bus

    best
    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
    6h 6m
    $120–667

  2. Fly from Chicago O'Hare International Airport, bus

    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 International Airport to Green Mountain Community Bus Terminalbus bus
    6h 36m
    $96–487

  3. Train, bus

    1. Take the train from Chicago Union Station to Albany-Rensselaer Amtrak Stationtrain train Lake Shore Limited
    2. Take the bus from AMTRAK Station Rensselaer to Green Mountain Community Bus Terminalbus bus 7
    18h 28m
    $237–511

  4. Bus via Brook Park

    1. Take the bus from Chicago Bus Station to Cleveland Bus Stationbus bus
    2. Take the bus from Cleveland Bus Station to Albany Bus Terminal, NYbus bus
    3. Take the bus from Greyhound \ Trailways Terminal to Green Mountain Community Bus Terminalbus bus 7
    20h 35m
    $151–291

  5. Drive 843.2 mi

    1. Drive from Chicago to Benningtoncar car 843.2 mi
    14h 43m
    $154–223

  6. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from New York, NY to Albany-Rensselaerbus bus Nyc
    3. Take the bus from AMTRAK Station Rensselaer to Green Mountain Community Bus Terminalbus bus 7
    23h 15m
    $143–257

Chicago to Bennington by train and bus

Calendar14Weekly Services
Duration18h 28mAverage Duration
Ticket$237Cheapest Price
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Questions & Answers

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

You can take a bus from Chicago Bus Station to Green Mountain Community Bus Terminal via Cleveland Bus Station and Greyhound \ Trailways Terminal in around 20h 35m.

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Need to know: Greyhound

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