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Travel Information
Compare train and flight for Chicago, IL to Bennington, VT
Omio recommends booking the train as it is the most popular option from Chicago, IL to Bennington, VT among Omio's users. If you are prioritising price take the train with prices starting from $210. For those with little time consider booking a flight which can get you there in 2h 13m. The ticket price range depends on the travel mode: a train costs an average of $210, and a flight costs an average of $457.
Distance: 740 miles (1191 km)
Compare train with
Most popular Train | Flight | Driving |
|---|---|---|
$210 Average price Cheapest | $457 Average price | $170 Average price (fuel + tolls) |
23h 0m Average total duration 22h 30m Onboard + 30m Additional time* | 5h 13m Average total duration Fastest 2h 13m Onboard + 3h 0m Additional time* | 12h 57m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chicago, IL to Bennington, VT:
A train is $248 (€203) less than a flight for this route with tickets for a flight from Chicago, IL to Bennington, VT costing on average $457 (€375).
Other travel options to Bennington, VT take longer:
Train takes on average 22h 30m.
Tickets start at around $210 (€172) compared to roughly $170 (€140) in fuel and tolls — a saving of about $-39.53 (€-32.40). The journey takes 22h 30m versus 12h 57m by car, so you'll arrive a bit later, but you can work, read, or sleep along the way rather than spending the time behind the wheel. You'll also save the hassle of parking at the other end.
Driving is worth it if you're on a tight schedule, travelling as a group, or want to stop somewhere en route.
Compare prices and tickets Chicago, IL to Bennington, VT by train or flight
Compare train and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
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Journey information
Overview: Train from Chicago, IL to Bennington, VT
USAUSA
Trains from Chicago, IL to Bennington, VT run on average 2 times per day, taking around 22h 30m. Cheap train tickets for this journey start at $210 (€172) if you book in advance.
The earliest train runs at 17:00, the last at 21:30. The fastest train covers the 740 miles (1191 km) distance in 22h 30m.
Distance 740 miles (1191 km) |
Average train duration 22h 30m |
Cheapest ticket price $210 (€172) |
Trains per day 2 |
Fastest train 22h 30m |
First train 5:00 PM |
Last train 9:30 PM |
Cheapest Month Sep |
Cheapest Day Sat |
High Season Jan - Mar |
Low Season Jul - Sep |
FAQs: Trains from Chicago, IL to Bennington, VT
Find answers to the most common questions about traveling from Chicago, IL to Bennington, VT by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Bennington, VT, this guide helps you travel smarter and with confidence.
popular train stations
Popular train stations from Chicago, IL to Bennington, VT
Most Chicago, IL to Bennington, VT trains use the Union Station to Bennington, Bennington Bus Terminal - 215 Pleasant Street station pair. Use this guide to compare Chicago, IL and Bennington, VT train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Which Chicago, IL station do trains to Bennington, VT leave from?
Getting to Union Station from Chicago city centre
Union Station is 3 km from Chicago city centre. Public transport options include:
Union Station train station facilities and services
Union Station has practical services for this route, including Wifi, Lockers, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lounge, Lost and Found Office, Ticket Office, Bike Parking, Car Rental, Information Desk, and Luggage Carts.
Food and drink
Food options include: The Chicago Firehouse Restaurant, Lou Mitchell's
Wi-Fi and ATMs
Free. ATMs are available in the train station.
Tickets and information
Ticket office support is available at Union Station. Information desks are located in the main hall.
Luggage and lost property
Luggage storage is available at Union Station. Lost and found is available at the station.
Parking, taxis and toilets
Available at Union Station: Parking, Taxis, WC.
Bike and car services
Available at Union Station: Bike Parking, Car Rental.
Accessibility
Accessibility facilities are available at Union Station: Elevators, ramps, restrooms.
Shops, hotels and contact
Nearby hotels include The Kimpton Gray Hotel, JW Marriott Chicago, W Chicago - City Center.
Most popular train connections from Chicago, IL
More options for your journey from Chicago, IL to Bennington, VT
Here are some other resources that might have the information you need
Most popular trains to and from Bennington, VT and Chicago, IL
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