Rome2Rio

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

Find Transport to Bennington

See all options

There are 5 ways to get from Chicago to Bennington by plane, bus, train, bus (Flixbus), 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 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
    $130–667

  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 37m
    $100–507

  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
    $111–276

  4. 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
    26h 20m
    $123–277

  5. Drive 843.1 mi

    1. Drive from Chicago to Benningtoncar car 843.1 mi
    14h 43m
    $154–223

Chicago to Bennington by train and bus

Calendar14Weekly Services
Duration18h 28mAverage Duration
Ticket$111Cheapest Price
See schedules

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 New York Midtown, New York, NY, and AMTRAK Station Rensselaer in around 26h 20m.

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

More Questions & Answers

Trips from Chicago

Trips to Bennington

Popular routes