Previously seen trips
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | Middlebury Amtrak Station | Chicago (Union Station), IL | No tags | ||||
| Train | Middlebury Amtrak Station | Chicago (Union Station), IL | No tags | ||||
| Train | Middlebury Amtrak Station | Chicago (Union Station), IL | No tags | ||||
| Train | Middlebury Amtrak Station | Chicago (Union Station), IL | No tags | ||||
| Train | Middlebury Amtrak Station | Chicago (Union Station), IL | No tags |
Get from Middlebury to Chicago
The journey takes about 1 day, 31 minutes and with fares starting at just $122, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5610 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $122
Frequently asked questions about traveling from Middlebury, VT to Chicago by train
Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.
How much is the train ticket from Middlebury to Chicago?
The cheapest train tickets from Middlebury to Chicago start from $122. The average price for this train route is around $187. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the train journey from Middlebury to Chicago?
The average train ride duration from Middlebury to Chicago is 1d , covering a distance of 744 miles (1200 km). The quickest train can get you there in 1d and is operated by Amtrak.
Which train operators service the Middlebury to Chicago route?
Several major train operators operate on this route with 1 trains available per day.
What is the earliest and latest departure time for the train from Middlebury to Chicago?
The earliest train departs from Middlebury to Chicago at 10:41am. And the latest train departs at 10:41am.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Middlebury, VT to Chicago was searched and found on Nov 27, 2025 with a price of $208To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Middlebury, VT to Chicago, as early as possible.
Top Traveled Train Routes
People from around the world trust Busbud
Popular train departures from Middlebury
- Find train tickets from Middlebury to Omaha
- Middlebury to Philadelphia train times and fares
- How to travel from Middlebury to New York City
- Find train tickets from Middlebury to Albany
- Middlebury to Burlington train times and fares
- How to travel from Middlebury to Boston
- Find train tickets from Middlebury to White River Junction