Compare 2 ways to go from Middlebury to Chicago.
Busbud recommends taking the bus from Middlebury to ChicagoAmong the sustainable travel choices, the bus stands out as the good way to reach Chicago. The journey takes about 20 hours 35 minutes and with fares starting at just $156, it presents an excellent value for a comfortable ride.
Train Middlebury, VT to Chicago: Trip Overview
Please note, this information is subject to change.
Train Companies
Based on 5343 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 $158
Middlebury to Chicago Train
Busbud helps you find a train from Middlebury to Chicago. Get the best fare and schedule, book a round trip ticket or find trains with WiFi and electrical outlets.
We make it our job to connect you with the most dependable companies that offer train service from Middlebury to Chicago.
Discover how much the train trip from Middlebury to Chicago will cost you. Use our filters and sorting features to find the cheapest train tickets or high-end trains.
Frequently asked questions for your trip Middlebury, VT - Chicago
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Middlebury, VT to Chicago was searched and found on Jul 26, 2025 with a price of $208To 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 $208 to $688 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 $230 which is on 2025-07-30.
About Train Travel
Train Travel Tips
There are many train stations in the world, check it station pages on Busbud to get all information you need.
Whether you take a regional or high-speed train to Chicago, you’ll help reduce the environmental impact and carbon footprint of your trip. As you watch the landscapes unfold before your eyes, you can tell yourself that with this choice, you are making sure they remain protected.
With up to 30x less CO2 emissions for your train journey between Middlebury and Chicago, the train is an ecological alternative to flights or personal cars.
Make a music playlist for your train ride from Middlebury to Chicago, and enjoy the scenery to tunes from your own personal soundtrack.
Did you know?
Japanese trains are always on time, it is extremely infrequent to see breakdowns during peak periods. In the event of a delay of more than 5 minutes, the crew will personally apologize to each passenger.
You can find the straightest railway in the world in Australia. This railway line is 478 kilometres long and is also considered the longest and straightest railway line in the world.
The longest train journey in the world is between Europe and Asia. This long journey starts from Porto in Portugal and crosses the whole European continent to reach Hanoi in Vietnam in 12 days while traveling more than 17,000 km.
Top Traveled Train Routes
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