How much does a train ticket from Chicago to Middlebury cost?

The average train ticket price from Chicago to Middlebury is $162. The best way to find 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 trains 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 you 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.

Train Chicago to Middlebury from $103 | Refundable Tickets

Previously seen trips

Next departures for Chicago to Middlebury on November 21
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	9:30pm	Chicago (Union Station), IL	22h 15m	8:45pm	Middlebury Amtrak Station	No tags
Train	9:30pm	Chicago (Union Station), IL	22h 15m	8:45pm	Middlebury Amtrak Station	No tags
Train	9:30pm	Chicago (Union Station), IL	22h 15m	8:45pm	Middlebury Amtrak Station	No tags
Train	9:30pm	Chicago (Union Station), IL	22h 15m	8:45pm	Middlebury Amtrak Station	No tags
Train	9:30pm	Chicago (Union Station), IL	22h 15m	8:45pm	Middlebury Amtrak Station	No tags

Get from Chicago to Middlebury

This route is served by train only

The journey takes about 22 hours 15 minutes and with fares starting at just $162, it presents an excellent value for a comfortable ride.

1train per day

22h 15mAverage Duration

744 milesDistance

109kgCO₂ emissions

Train Companies

Amtrak

4/55,597 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wifi3.6

Based on 5597 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

Train and bus companies in US:Amtrak, Trenitalia, Renfe, VIA Rail Canada, Amtrak Acela, NS Nederlandse Spoorwegen, Iryo

Frequently asked questions about traveling from Chicago to Middlebury, VT by train

How much does a train ticket from Chicago to Middlebury cost?
How long is the train trip from Chicago to Middlebury?
How many daily trains are there between Chicago and Middlebury?
Which train companies travel from Chicago to Middlebury?

Find cheapest prices for trains

Price is for a one-way ticket for one passenger and based on past searches.

Best price found

11/19

No data

11/20

$208

Today

No data

11/22

No data

11/23

No data

11/24

No data

11/25

No data

11/26

$116

The cheapest trip from Chicago to Middlebury, VT was searched and found on Nov 26, 2025 with a price of $116

To 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 $116 to $1,553 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 $116 which is on 2025-11-26.