How much is the train ticket from Middlebury to Chicago?

The cheapest train tickets from Middlebury to Chicago start from $162. 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.

Train Middlebury to Chicago from $155 | Refundable Tickets

Next train departures

Next departures for Middlebury to Chicago on January 4
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	CheapestFastest
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

Next departures for Middlebury to Chicago on January 5
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	CheapestFastest
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

Next departures for Middlebury to Chicago on January 6
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	CheapestFastest
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

Next departures for Middlebury to Chicago on January 7
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	CheapestFastest
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

Next departures for Middlebury to Chicago on January 8
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	CheapestFastest
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

Last refresh of the prices: Last Wednesday at 9:18 PM EST.

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 $162, it presents an excellent value for a comfortable ride.

1train per day

1d Average Duration

744 milesDistance

109kgCO₂ emissions

Train Companies

Amtrak

4/55,699 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wifi3.6

Based on 5699 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

US train companies:Amtrak, Trenitalia, Renfe, VIA Rail Canada, Amtrak Acela, NS Nederlandse Spoorwegen, Iryo

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 $162. 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.

Best price found

01/01

$287

01/02

$287

Today

$243

01/04

$243

01/05

$155

01/06

$155

01/07

$155

01/08

$155

The cheapest trip from Middlebury, VT to Chicago was searched and found on Jan 5, 2026 with a price of $155

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 $155 to $1,212 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 $155 which is on 2026-01-05.