Chicago, IL to Bennington, VT train

Mon, May 18
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Regionale
Deutsche Bahn
iryo
Frecciarossa
AVE
2,000+ travel companies
Regionale
Deutsche Bahn
iryo
Frecciarossa
AVE
2,000+ travel companies
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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 $213. 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 $213, and a flight costs an average of $464.

Distance: 740 miles (1191 km)

Compare train with

Most popular
Train
Flight
Driving

$213

Average price

Cheapest

$464

Average price

$173

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

The cheapest way to travel from Chicago, IL to Bennington, VT is a train with an average price of $213 (€172).

This is compared to other travel options from Chicago, IL to Bennington, VT:

A train is $251 (€203) less than a flight for this route with tickets for a flight from Chicago, IL to Bennington, VT costing on average $464 (€375).

The fastest way to travel from Chicago, IL to Bennington, VT is by flight with an average journey time of 2h 13m.

Other travel options to Bennington, VT take longer:

Train takes on average 22h 30m.

It's helpful to compare your options as there are 2 ways to travel between Chicago, IL and Bennington, VT including taking a train and flight.
Take the train. It's the cheaper option, and the extra time on board is usually more relaxing than driving it.

Tickets start at around $213 (€172) compared to roughly $173 (€140) in fuel and tolls — a saving of about $-40.12 (€-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.

Mon
May 18
Tue
May 19
Wed
May 20
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May 21
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May 22
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May 24

Journey information

Overview: Train from Chicago, IL to Bennington, VT

USAUSA
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Icon of train

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 $213 (€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.

Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Distance
740 miles (1191 km)
Average train duration
22h 30m
Cheapest ticket price
$213 (€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
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information

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.

FAQs
Train ticket prices from Chicago, IL to Bennington, VT can vary. The cheapest ticket starts at $213 (€172), while the average price is around $213 (€172).
The train from Chicago, IL to Bennington, VT takes 22h 30m and runs 2 per day.
The distance by train from Chicago, IL to Bennington, VT is 740 miles (1191 km).
The first train from Chicago, IL to Bennington, VT leaves at 5:00 PM.
The last train from Chicago, IL to Bennington, VT leaves at 9:30 PM.
Unfortunately, there is no night train available from Chicago, IL to Bennington, VT.
The cheapest way to get from Chicago, IL to Bennington, VT is by train, with a cost of around $213 (€172).
The train journey from Chicago, IL to Bennington, VT offers scenic views, especially as it passes through the picturesque landscapes of upstate New York and the Green Mountains in Vermont, providing a pleasant and visually appealing experience.
Spending 2-3 days in Bennington, VT is ideal, allowing time to explore the Bennington Battle Monument, enjoy the local art scene at the Bennington Museum, and experience the natural beauty of nearby hiking trails.
No, you cannot take the train from Chicago, IL to Bennington, VT.
Since neither Chicago, IL nor Bennington, VT are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
Items not allowed on trains typically include hazardous materials such as explosives, flammable liquids, corrosive substances, and illegal drugs. Additionally, large or bulky items that may obstruct aisles or emergency exits, as well as pets without proper carriers, may be restricted. Specific prohibited items can vary by train operator and region, so please check the rules for your particular journey.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Bennington, VT, travelers should be aware of typical small-town safety concerns such as petty theft and occasional vehicle break-ins. It is advisable to secure valuables and park in well-lit areas. There are no widespread reports of specific scams targeting visitors, but common travel scams like overcharging and fake tickets can occur, so travelers should purchase transportation tickets through official channels to avoid fraud.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.

popular train stations

Popular train stations from Chicago, IL to Bennington, VT

Chicago
Bennington
The major train station for departures in Chicago is Union Station. Find all the information you need to know about services, amenities and connections at Union Station for your trip from Chicago to Bennington.
Union StationWifiLockersParkingDiningATMTaxisAccessibilityWCHotelLoungeLost and Found OfficeTicket OfficeBike ParkingCar RentalInformation DeskLuggage Carts
Amenities at train station
WifiWifi
LockersLockers
ParkingParking
DiningDining
ATMATM
TaxisTaxis
AccessibilityAccessibility
WCWC
HotelHotel
LoungeLounge
Lost and Found OfficeLost and Found Office
Ticket OfficeTicket Office
Bike ParkingBike Parking
Car RentalCar Rental
Information DeskInformation Desk
Luggage CartsLuggage Carts
information
address
Address
225 South Canal Street, Chicago, IL 60606, USA
phone
Phone Number
ticketOfficeHours
Ticket Office Hours
  • 5:00 AM - 12:00 AM Monday - Sunday
ticketOfficeHours
Distance to city center
3 km
platformCount
Number of platforms
24
Wifi
Wifi
  • Free
Parking
Parking
  • 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.
Dining
Dining
  • The Chicago Firehouse Restaurant
  • Lou Mitchell's
Taxis
Taxis
  • Outside the main entrance.
Accessibility
Accessibility
  • Elevators, ramps, restrooms.
WC
WC
  • $1
Hotel
Hotel
  • The Kimpton Gray Hotel
  • JW Marriott Chicago
  • W Chicago - City Center
Lounge
Lounge
  • Located in the main hall
Lost and Found Office
Lost and Found Office
  • Located in the main hall
Car Rental
Car Rental
  • Avis
  • Budget
  • Enterprise
Information Desk
Information Desk
  • Located in the main hall
Luggage Carts
Luggage Carts
  • Free
Station Plan
  • Hall 1: main entrance, Amtrak services
  • Hall 2: Metra services
  • Hall 3: food court and retail shops
Public transit options for Union Station
  • Bus: Several lines available
  • CTA: Blue Line, Pink Line

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