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Compare prices and tickets Windsor, VT to Chicago, IL by train
Compare train prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
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Journey information
Overview: Bus from Windsor, VT to Chicago, IL
Take a bus from Windsor, VT to Chicago, IL and enjoy the approximately 782 miles (1259 km) long journey. Find schedules and pricing options for a convenient and affordable trip.
The earliest bus runs at 05:20, the last at 23:15.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Train from $356 (€291)
Distance 782 miles (1259 km) |
Buses per day 2 |
First bus 05:20 |
Last bus 23:15 |
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Train from $356 (€291)
FAQs: Bus from Windsor, VT to Chicago, IL
Find answers to the most common questions about traveling from Windsor, VT to Chicago, IL by bus. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest bus, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

Cheap bus tickets from Windsor, VT to Chicago, IL can start from as little as $168 (€137) when you book in advance. The average bus ticket price for Windsor, VT to Chicago, IL is $199 (€163); however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
On average the Windsor, VT to Chicago, IL bus time is 31 h 40 min covering the 781 mile (1259 km) long route, but the journey time can vary depending on specific dates or if traveling on weekends and holidays.
The first bus from Windsor, VT to Chicago, IL leaves at 5: 20AM. Plan your trip with the Journey Planner from Omio.
The last bus from Windsor, VT to Chicago, IL leaves at 10: 50PM.
The cheapest month to travel from Windsor, VT to Chicago, IL by bus is October.
You have options as you can travel between Windsor, VT and Chicago, IL 2 different ways: train or bus.
No, the bus from Windsor, VT to Chicago, IL has no accessibility options.
No, there are no bathrooms on board the bus from Windsor, VT to Chicago, IL.
Some of the most interesting sights to explore in Chicago, IL are:
- Millennium Park, a public park known for its modern art installations and the iconic Cloud Gate sculpture
- Art Institute of Chicago, a renowned museum housing an extensive collection of art from around the world
- Navy Pier, a popular entertainment destination featuring rides, restaurants, and lakefront views
- Willis Tower Skydeck, an observation deck offering panoramic views of the city from one of the tallest buildings in the Western Hemisphere
- Field Museum, a natural history museum with vast exhibits including the famous T. Rex skeleton, Sue.
The best things to do in Chicago, IL include:
- Museum of Science and Industry, an interactive museum featuring exhibits on science, technology, and industry
- Explore the vibrant neighborhoods of Chicago, such as Wicker Park and Lincoln Park, known for their unique shops and eateries
- Take a river cruise to see the city's iconic architecture from a different perspective
- Attend a live performance at the historic Chicago Theatre
- Enjoy a day at Lincoln Park Zoo, one of the oldest zoos in the U. S. Offering free admission.
No, bikes are not allowed on board the bus from Windsor, VT to Chicago, IL.
To find the cheapest bus tickets for your trip from Windsor, VT to Chicago, IL, follow these tips:
Start your search now and compare ticket prices to find the best deal!
Yes, there is food available to purchase on board the bus from Windsor, VT to Chicago, IL.
No, luggage for the bus from Windsor, VT to Chicago, IL needs to be booked in addition.
No, there are no additional luggage options for the bus from Windsor, VT to Chicago, IL.
Unfortunately, pets are not allowed on the bus from Windsor, VT to Chicago, IL.
No, there are no USB plugs on board the bus from Windsor, VT to Chicago, IL.
No, there is no WiFi on board the bus from Windsor, VT to Chicago, IL.
popular bus stations
Popular bus stations from Windsor, VT to Chicago, IL
Windsor
Chicago
Chicago, Greyhound Bus Station
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Chicago, Union Station (Amtrak)
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