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The cheapest and fastest buses from Windsor, ON to Chicago, IL
Showing times and prices for Dec 01
Cheapest price
$84
Average price
$127
Fastest journey
4 h 10 m
Average duration
6 h 8 m
Buses per day
4
Distance
386 km
Cheap tickets
The best way to find a cheap bus ticket from Windsor, ON to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Windsor, ON to Chicago, IL will cost around $127 if you buy it on the day, but the cheapest tickets can be found for only $84.
Fast buses
Of the 4 buses that leave Windsor, ON for Chicago, IL on Mon, Dec 01, 3 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Mon, Dec 01 the direct buses cover the 386 km distance in an average of 6 h 8 m but if you time it right, some buses will get you there in just 4 h 10 m .
On Mon, Dec 01 the slowest buses will take 9 h 35 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.
09:45AM4h10
Windsor, ON01:55PMChicago, IL
$841One-way
0 transfers
10:30AM9h35
Windsor, ON08:05PMChicago, IL
$1311One-way
1 transfer
08:35AM5h45
Windsor, ON02:20PMChicago, IL
$1461One-way
0 transfers
04:20PM5h00
Windsor, ON09:20PMChicago, IL
$1461One-way
0 transfers
09:45AM4h10
Windsor, ON01:55PMChicago, IL
$841One-way
0 transfers
04:20PM5h00
Windsor, ON09:20PMChicago, IL
$1461One-way
0 transfers
08:35AM5h45
Windsor, ON02:20PMChicago, IL
$1461One-way
0 transfers
10:30AM9h35
Windsor, ON08:05PMChicago, IL
$1311One-way
1 transfer
Windsor, ON to Chicago, IL Bus Timetables
| Operator | Departure Time | Arrival Time | Duration | Departure days | Cheapest price |
|---|---|---|---|---|---|
Operator Greyhound | Departure Time 08:35PM | Arrival Time 05:35AM | Duration 10h00 | Departure days Sun | Cheapest price $279 |
Live departures
Windsor, ON to Chicago, IL bus times
The table below shows live departures for Windsor, ON to Chicago, IL buses for tomorrow, Monday, December 1. You can also manually refresh the results below to see updated bus journeys.
Last updated at 5:11 AM
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| FlixBus+ | 1:35 AM Windsor, Chatham St W (Windsor Transit Terminal) | 10h00 | 11:35 AM Chicago, Greyhound Bus Station | 1 transfer | |
This is the last bus of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Windsor, ON to Chicago, IL by bus or train
Compare bus and 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.
Mon
Dec 01
Dec 01
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Dec 02
Dec 02
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Dec 07
Dec 07
Journey information
Overview: Bus from Windsor, ON to Chicago, IL
Canada
USA
Buses from Windsor, ON to Chicago, IL run on average 2 times per day, taking around 6h 23m. Cheap bus tickets for this journey start at $85 (€69) if you book in advance.
The earliest bus runs at 05:00, the last at 23:25. The fastest bus covers the 239 miles (386 km) distance in 4h 10m.
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
Distance 239 miles (386 km) |
Average bus duration 6h 23m |
Cheapest ticket price $85 (€69) |
Buses per day 2 |
Fastest bus 4h 10m |
First bus 05:00 |
Last bus 23:25 |
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
Bus providers: Miller Transportation, Greyhound, FlixBus from Windsor, ON to Chicago, ILYou can travel by bus between Windsor, ON to Chicago, IL with Miller Transportation, Greyhound, FlixBus for as low as $85 (€69). When you search for schedules and tickets, Omio will show you the best journey
FlixBus
About
FlixBus is one of Europe’s leading low-cost bus companies, founded in Germany and now offering long-distance services across Europe and the United States. In addition to its extensive daytime network, FlixBus also operates overnight buses on select European routes. Standard amenities include free Wi-Fi, power outlets to charge devices, extra legroom, luggage space, and onboard toilets, with snacks and drinks available for purchase. FlixBus offers a single Standard ticket type for all routes, which includes one carry-on bag and one checked bag per passenger. Additional fees apply for extra luggage and for reserving specific seats, such as Extra Seats, Table Seats, or Panorama Seats. This combination of affordability, comfort, and wide coverage makes FlixBus a popular choice for budget-conscious travelers.
Luggage & cancellation policy
Average Duration
4h 10m
Cheapest Price
$84 (€68)
FlixBus frequency
1 a day
Luggage included
One carry-on bag up to 7kg (42x30x18 cm) and one checked bag up to 20kg (80x50x30 cm).
Additional luggage
Additional luggage can be purchased for a fee.
Cancellation Policy
You can cancel your ticket up to 15 minutes before departure and receive a voucher for future travel. Refund requests for delays over 120 minutes are possible.
Amenities on board the bus
Wifi
Food sold onboard
Seat reservation
Toilets
USB plugs
Accessibility
Assistance; Priority boarding; Wheelchair-accessible buses.
Bikes
Bikes are allowed for a fee; must be booked.
Pets
Small pets in carriers allowed; guide dogs travel for free.
Greyhound
About
Greyhound Lines, Inc. is a prominent American intercity bus transportation provider, established in 1914. It operates the largest intercity bus network in the United States, also extending services to Canada and Mexico. Greyhound is known for offering affordable and reliable long-distance travel, connecting major cities and rural communities across North America. The company's buses are equipped with amenities such as free Wi-Fi, power outlets, and extra legroom to enhance passenger comfort. Greyhound is a subsidiary of Flix SE, which also owns FlixBus, and together they offer an extensive network of over 1,600 destinations.
Luggage & cancellation policy
Average Duration
8h 30m
Cheapest Price
$73 (€59)
Greyhound frequency
2 a day
Luggage included
One carry-on bag up to 25 lbs (11 kg) and one checked bag up to 50 lbs (23 kg).
Additional luggage
$15 per additional bag.
Cancellation Policy
You can cancel your ticket for a refund or exchange up to 24 hours before departure, for a cancellation fee applied.
Amenities on board the bus
Wifi
Food sold onboard
Seat reservation
Toilets
USB plugs
Accessibility
Assistance; Priority seating; Wheelchair-accessible buses.
Bikes
Bikes are allowed.
Miller Transportation
Luggage & cancellation policy
Average Duration
9h 35m
Cheapest Price
$131 (€106)
Miller Transportation frequency
1 a day
FAQs: Bus from Windsor, ON to Chicago, IL
Find answers to the most common questions about traveling from Windsor, ON 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, ON to Chicago, IL can start from as little as $41 (€33) when you book in advance. The average bus ticket price for Windsor, ON to Chicago, IL is $60 (€48); however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The bus time from Windsor, ON to Chicago, IL is on average 7 h 50 min for the 239 mile (385 km) long journey, but the time it takes to go to Chicago, IL from Windsor, ON by bus can vary depending on specific dates or if traveling on weekends and holidays.
The first bus from Windsor, ON to Chicago, IL leaves at 1: 45AM. Plan your trip with the Journey Planner from Omio.
The last bus from Windsor, ON to Chicago, IL leaves at 11: 25PM.
There are 2 buses a day from Windsor, ON to Chicago, IL which require at least one change with Greyhound, FlixBus or Miller Transportation. Schedules can vary on holidays or weekends with fewer buses.
For the best Windsor, ON to Chicago, IL bus to book, you can travel safely and comfortably with Greyhound, FlixBus or Miller Transportation. However, it's always good to check all possible bus providers with services between Windsor, ON and Chicago, IL to compare what amenities they may offer.
The cheapest month for a bus from Windsor, ON to Chicago, IL is November.
You have options as you can travel to Chicago, IL from Windsor, ON 2 different ways: bus or train.
Yes, the following accessibility options are available when taking the bus from Windsor, ON to Chicago, IL:
- Greyhound
- Assistance
- Priority seating
- Wheelchair-accessible buses.
- FlixBus
- Assistance
- Priority boarding
- Wheelchair-accessible buses.
Yes, there are bathrooms on board the bus from Windsor, ON to Chicago, IL for bus companies Greyhound and FlixBus.
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.
Yes, bikes are allowed on board the bus with bus companies Greyhound and FlixBus.
Whether you can cancel your bus ticket from Windsor, ON to Chicago, IL depends on the bus providers:
- Greyhound
- You can cancel your ticket for a refund or exchange up to 24 hours before departure, for a cancellation fee applied.
- FlixBus
- You can cancel your ticket up to 15 minutes before departure and receive a voucher for future travel. Refund requests for delays over 120 minutes are possible.
To find the cheapest bus tickets for your trip from Windsor, ON 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, ON to Chicago, IL.
Yes, the following luggage options are included when booking a bus ticket from Windsor, ON to Chicago, IL:
- Greyhound
- One carry-on bag up to 25 lbs (11 kg) and one checked bag up to 50 lbs (23 kg).
- FlixBus
- One carry-on bag up to 7kg (42x30x18 cm) and one checked bag up to 20kg (80x50x30 cm).
Yes, the following additional luggage options are available when booking a bus ticket from Windsor, ON to Chicago, IL:
- Greyhound
- $15 per additional bag.
- FlixBus
- Additional luggage can be purchased for a fee.
Yes, you can bring your pet on the bus from Windsor, ON to Chicago, IL. The following conditions apply:
- FlixBus
- Small pets in carriers allowed
- Guide dogs travel for free.
You can reserve your seat on the bus from Windsor, ON to Chicago, IL with the following bus providers: Greyhound and FlixBus
Yes, there are USB plugs on board the bus from Windsor, ON to Chicago, IL with the following bus providers: Greyhound and FlixBus.
Yes, there is Wifi on board the bus from Windsor, ON to Chicago, IL with the following bus companies: Greyhound and FlixBus.
popular bus stations
Popular bus stations from Windsor, ON to Chicago, IL
Windsor
Chicago
The major bus station for departures in Windsor is Windsor, Chatham St W (Windsor Transit Terminal). Find all the information you need to know about services, amenities and connections at Windsor, Chatham St W (Windsor Transit Terminal) for your trip from Windsor to Chicago.
Windsor, Chatham St W (Windsor Transit Terminal)
information
The major bus station for arrivals in Chicago is Chicago, Greyhound Bus Station. Find all the information you need to know about services, amenities and connections at Chicago, Greyhound Bus Station for your trip to Chicago from Windsor.
Chicago, Greyhound Bus Station
information
Most popular bus connections from Windsor, ON
More options for your journey from Windsor, ON to Chicago, IL
Here are some other resources that might have the information you need
Most popular buses to and from Chicago, IL and Windsor, ON
Most popular bus connections to Chicago, IL
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