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 $171. For those with little time consider booking a flight which can get you there in 2h 5m. The ticket price range depends on the travel mode: a train costs an average of $171, and a flight costs an average of $360.
Distance: 740 miles (1191 km)
Compare train with
Most popular Train | Flight |
|---|---|
$171 Average price Cheapest | $360 Average price |
23h 0m Average total duration 22h 30m Onboard + 30m Additional time* | 5h 5m Average total duration Fastest 2h 5m Onboard + 3h 0m Additional time* |
Direct Options | Direct Options |
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
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 $171 (€139) if you book in advance.
The earliest train runs at 16:25, 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 $171 (€139) |
Trains per day 2 |
Fastest train 22h 30m |
First train 16:25 |
Last train 21:30 |
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
- 5:00 AM - 12:00 AM Monday - Sunday
- Free
- The car park is open 7 days a week from 5:00 a.m. to 12:00 a.m. Departures can be made outside of opening hours. Access via Canal Street.
- The Chicago Firehouse Restaurant
- Lou Mitchell's
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $1
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
- Located in the main hall
- Located in the main hall
- Avis
- Budget
- Enterprise
- Located in the main hall
- Free
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
- Bus: Several lines available
- CTA: Blue Line, Pink Line
Most popular train connections from Chicago, IL
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