Previously seen journeys
| 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 £126, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5607 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi-Fi. Amtrak ticket prices on this trip start at £126
Frequently asked questions about travelling from Chicago to Middlebury, VT by train
How much does a cheap train ticket from Chicago to Middlebury cost?
The average train ticket price from Chicago to Middlebury is £126. The best way to find cheap train tickets from Chicago to Middlebury is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the train trip from Chicago to Middlebury?
A train trip between Chicago and Middlebury is around 22h 15m, although the fastest train will take about 22h 15m. This is the time it takes to travel the 746 miles that separates the two cities.
How many daily train are there between Chicago and Middlebury?
The number of trains from Chicago to Middlebury can differ depending on the day of the week. On average, there is 1. Some trains are direct while others have layovers. Simplify your train trip from Chicago to Middlebury by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from Chicago to Middlebury?
When taking the train from Chicago to Middlebury, you can travel comfortably and safely with Amtrak.
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 26 Nov 2025 with a price of £90To 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 £90 to £491 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 £90, which is on 2025-11-27.
