Previously seen trips
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | Chicago (Union Station), IL | Middlebury Amtrak Station | No tags | ||||
| Train | Chicago (Union Station), IL | Middlebury Amtrak Station | No tags | ||||
| Train | Chicago (Union Station), IL | Middlebury Amtrak Station | No tags | ||||
| Train | Chicago (Union Station), IL | Middlebury Amtrak Station | No tags | ||||
| Train | Chicago (Union Station), IL | Middlebury Amtrak Station | No tags |
Get from Chicago to Middlebury
The journey takes about 22 hours 15 minutes and with fares starting at just $162, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5621 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 $162
Frequently asked questions about traveling from Chicago to Middlebury, VT 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 Chicago to Middlebury?
The cheapest train tickets from Chicago to Middlebury start from $162. The average price for this train route is around $162. 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 Chicago to Middlebury?
The average train ride duration from Chicago to Middlebury is 22h 15m, covering a distance of 744 miles (1200 km). The quickest train can get you there in 22h 15m and is operated by Amtrak.
Which train operators service the Chicago to Middlebury 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 Chicago to Middlebury?
The earliest train departs from Chicago to Middlebury at 9:30pm. And the latest train departs at 9:30pm.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Chicago to Middlebury, VT was searched and found on Dec 5, 2025 with a price of $103To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Chicago to Middlebury, VT, as early as possible.
You can expect to pay from $103 to $2,014 for a train ticket from Chicago to Middlebury, VT based on the last 2 days. You can expect to find the cheapest price for the trip at $103 which is on 2025-12-05.
