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

The average train ticket price from Middlebury to Chicago is $187. The best way to find train tickets from Middlebury to Chicago 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 Middlebury to Chicago?

A train trip between Middlebury and Chicago is around 1d , although the fastest train will take about 1d . This is the time it takes to travel the 746 miles that separates the two cities.

How many daily trains are there between Middlebury and Chicago?

The number of trains from Middlebury to Chicago 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 Middlebury to Chicago by comparing and selecting the train that fits you travel style and budget on Busbud.

Which train companies travel from Middlebury to Chicago?

When taking the train from Middlebury to Chicago, you can travel comfortably and safely with Amtrak.

What are the best sights and things to do in Chicago?

Once in Chicago, you can explore the city. The top sights and things to do are Museum of Contemporary Art, Willis Tower (Sears Tower), Chicago Shakespeare Theater on Navy Pier, Navy Pier, Lincoln Park Zoo.

Train Middlebury to Chicago from $116 | Refundable Tickets

Previously seen trips

Next departures for Middlebury to Chicago on November 23
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	10:41am	Middlebury Amtrak Station	1d	10:12am	Chicago (Union Station), IL	No tags
Train	10:41am	Middlebury Amtrak Station	1d	10:12am	Chicago (Union Station), IL	No tags
Train	10:41am	Middlebury Amtrak Station	1d	10:12am	Chicago (Union Station), IL	No tags
Train	10:41am	Middlebury Amtrak Station	1d	10:12am	Chicago (Union Station), IL	No tags
Train	10:41am	Middlebury Amtrak Station	1d	10:12am	Chicago (Union Station), IL	No tags

Get from Middlebury to Chicago

This route is served by train only

The journey takes about 1 day, 31 minutes and with fares starting at just $122, it presents an excellent value for a comfortable ride.

1train per day

1d Average Duration

744 milesDistance

109kgCO₂ emissions

Train Companies

Amtrak

4/55,600 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wifi3.6

Based on 5600 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

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

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

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

Find cheapest prices for trains

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

Best price found

11/21

$287

11/22

No data

Today

No data

11/24

$243

11/25

No data

11/26

No data

11/27

No data

11/28

No data

The cheapest trip from Middlebury, VT to Chicago was searched and found on Nov 24, 2025 with a price of $243

To 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.

You can expect to pay from $243 to $862 for a train ticket from Middlebury, VT to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $243 which is on 2025-11-24.