- Must visit
Art Windsor-Essex
Windsor’s main art museum presents Canadian and international works, with a strong focus on contemporary and regional art.
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The cheapest and fastest buses from Chicago, IL to Windsor, ON
Showing times and prices for Aug 04
Cheapest price
€62
Average price
€74
Fastest journey
7 h 30 m
Average duration
10 h 29 m
Buses per day
4
Distance
386 km
Cheap tickets
The best way to find a cheap bus ticket from Chicago, IL to Windsor, ON is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chicago, IL to Windsor, ON will cost around €74 if you buy it on the day, but the cheapest tickets can be found for only €62.
Fast buses
It's difficult to get from Chicago, IL to Windsor, ON without transferring at least once.
+
FlixBus3:55 PM7h30Chicago, Greyhound Bus Station12:25 AMWindsor, Chatham St W (Windsor Transit Terminal)€621One-way1 transfer- +FlixBus11:35 PM11h50Chicago, Greyhound Bus Station12:25 PMWindsor, Chatham St W (Windsor Transit Terminal)€621One-way1 transfer
- · +FlixBus6:30 AM9h25Chicago, Greyhound Bus Station4:55 PMWindsor, Chatham St W (Windsor Transit Terminal)€861One-way2 transfers
- · · +FlixBus10:15 AM13h10Chicago, Union Station (Amtrak), IL12:25 AMWindsor, Chatham St W (Windsor Transit Terminal)€871One-way3 transfers
- +FlixBus3:55 PM7h30Chicago, Greyhound Bus Station12:25 AMWindsor, Chatham St W (Windsor Transit Terminal)€621One-way1 transfer
- · +FlixBus6:30 AM9h25Chicago, Greyhound Bus Station4:55 PMWindsor, Chatham St W (Windsor Transit Terminal)€861One-way2 transfers
- +FlixBus11:35 PM11h50Chicago, Greyhound Bus Station12:25 PMWindsor, Chatham St W (Windsor Transit Terminal)€621One-way1 transfer
- · · +FlixBus10:15 AM13h10Chicago, Union Station (Amtrak), IL12:25 AMWindsor, Chatham St W (Windsor Transit Terminal)€871One-way3 transfers
Travel Information
Compare bus, train, and flight for Chicago, IL to Windsor, ON
Omio recommends booking the train as it is the most popular option from Chicago, IL to Windsor, ON among Omio's users. If you are prioritising price take the train with prices starting from €35. For those with little time consider booking a train which can get you there in 5h 35m. The ticket price range depends on the travel mode: a train costs an average of €35, and a flight costs an average of €238.
Distance: 239 miles (386 km)
Compare bus with
| Bus | Most popular Train | Flight | Driving |
|---|---|---|---|
€56 Average price | €45 Average price Cheapest | €427 Average price | €60 Average price (fuel + tolls) |
7h 33m Average total duration 7h 3m Onboard + 30m Additional time* | 6h 5m Average total duration Fastest 5h 35m Onboard + 30m Additional time* | 10h 33m Average total duration 7h 33m Onboard + 3h 0m Additional time* | 4h 12m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
The cheapest way to travel from Chicago, IL to Windsor, ON is a train with an average price of €45.
This is compared to other travel options from Chicago, IL to Windsor, ON:
A train is €11 less than a bus for this route with tickets for a bus from Chicago, IL to Windsor, ON costing on average €56.
A train is €382 less than a flight for this route with tickets for a flight from Chicago, IL to Windsor, ON costing on average €427.
The fastest way to travel from Chicago, IL to Windsor, ON is by train with an average journey time of 5h 35m.
Other travel options to Windsor, ON take longer:
Bus takes on average 7h 3m.
Flight takes on average 7h 33m.
It's helpful to compare your options as there are 3 ways to travel between Chicago, IL and Windsor, ON including taking a bus, train, and flight.
We recommend using the train as it is the most popular way to get from Chicago, IL to Windsor, ON among Omio's users.
Take the bus. It's the cheapest way to make this trip, and the price gap is usually bigger than people expect.
Tickets start at around €56 compared to roughly €60 in fuel and tolls — a saving of about €3. The journey takes 7h 3m versus 4h 12m by car, so you'll arrive a bit later, but you can use the time productively rather than spending it behind the wheel. No parking to sort, no fuel stops, and most coaches have Wi-Fi and power outlets.
Direct services are operated by Greyhound, FlixBus.
Driving is worth considering if you're on a tight schedule, travelling as a group (where fuel costs split several ways), or want the flexibility to stop along the way.
Chicago, IL to Windsor, ON Bus Timetables
| Operator | Departure Time | Arrival Time | Duration | Departure days | Cheapest price |
|---|---|---|---|---|---|
Operator Greyhound | Departure Time 04:35AM | Arrival Time 04:25PM | Duration 11h50 | Departure days Thu, Fri | Cheapest price €61 |
Operator Greyhound USA | Departure Time 06:20AM | Arrival Time 02:45PM | Duration 8h25 | Departure days Sun | Cheapest price €60 |
Operator Greyhound | Departure Time 06:30AM | Arrival Time 04:55PM | Duration 9h25 | Departure days Mon, Tue, Fri, Sat | Cheapest price €36 |
Operator Flixbus USA | Departure Time 09:30AM | Arrival Time 06:25PM | Duration 8h55 | Departure days Mon, Sat, Sun | Cheapest price €36 |
Operator Greyhound | Departure Time 10:15AM | Arrival Time 12:25AM | Duration 13h10 | Departure days Mon, Tue, Fri, Sat | Cheapest price €46 |
Operator Greyhound | Departure Time 01:00PM | Arrival Time 09:55PM | Duration 8h55 | Departure days Wed, Thu | Cheapest price €39 |
Operator Flixbus USA | Departure Time 02:30PM | Arrival Time 08:40PM | Duration 6h10 | Departure days Sun | Cheapest price €40 |
Operator Greyhound USA | Departure Time 03:55PM | Arrival Time 11:00PM | Duration 7h05 | Departure days Mon, Tue, Fri, Sat, Sun | Cheapest price €36 |
Operator Greyhound USA | Departure Time 11:35PM | Arrival Time 06:50AM | Duration 7h15 | Departure days Mon, Tue, Fri, Sat, Sun | Cheapest price €36 |
Live departures
Chicago, IL to Windsor, ON bus times
The table below shows live departures for Chicago, IL to Windsor, ON buses for today, Monday, August 3. You can also manually refresh the results below to see updated bus journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| +FlixBus | 11:35 PM Chicago, Greyhound Bus Station | 11h50 | 12:25 PM Windsor, Chatham St W (Windsor Transit Terminal) | 1 transfer | |
| Tuesday, August 4 | |||||
| · +FlixBus | 6:30 AM Chicago, Greyhound Bus Station | 9h25 | 4:55 PM Windsor, Chatham St W (Windsor Transit Terminal) | 2 transfers | |
| · · +FlixBus | 10:15 AM Chicago, Union Station (Amtrak), IL | 13h10 | 12:25 AM Windsor, Chatham St W (Windsor Transit Terminal) | 3 transfers | |
| +FlixBus | 3:55 PM Chicago, Greyhound Bus Station | 7h30 | 12:25 AM Windsor, Chatham St W (Windsor Transit Terminal) | 1 transfer | |
This is the last bus of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Chicago, IL to Windsor, ON by bus, train, or flight
Compare bus, train, and flight 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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Aug 04
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Aug 10
Why should you book Chicago, IL to Windsor, ON buses with Omio?
Greyhound as well as FlixBus offer buses services from Chicago, IL to Windsor, ON.
Omio is an official ticket reseller for all your travel options from Chicago, IL to Windsor, ON.
Why book with Omio vs Greyhound?
- Compare with other providers: On Omio, you can not only buy tickets for Greyhound, but also compare tickets for the likes of FlixBus to find the best option for your trip from Chicago, IL to Windsor, ON.
- Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
- Compare all your options: Omio allows you to compare Greyhound with all available travel options, which are bus, train and flight to ensure you get the best deal for traveling from Chicago, IL to Windsor, ON.
Why book with Omio over Wanderu or Trainline?
- Compare with other providers: On Omio, you can also compare tickets for the likes of FlixBus to find the best option for your trip from Chicago, IL to Windsor, ON.
- Multiple modes of transport: Omio allows you to compare travel options including bus, train and flight to find the ideal travel option from Chicago, IL to Windsor, ON.
Journey information
Overview: Bus from Chicago, IL to Windsor, ON
USA
Canada
Buses from Chicago, IL to Windsor, ON run on average 4 times per day, taking around 7h 3m. Cheap bus tickets for this journey start at €39 but you can travel from only €35 by train.
The earliest bus runs at 05:00, the last at 23:55. The fastest bus covers the 239 miles (386 km) distance in 7h 30m.
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 €35
Distance 239 miles (386 km) |
Average bus duration 7h 3m |
Cheapest ticket price €39 |
Buses per day 4 |
Fastest bus 7h 30m |
First bus 5:00 AM |
Last bus 11:55 PM |
Cheapest Month Dec |
Cheapest Day Thu |
High Season Apr - Jun |
Low Season Jan - Mar |
Busiest Day Sat |
Least Busy Day Sat |
Best time to book 1 day |
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 €35
Bus providers: Greyhound, FlixBus from Chicago, IL to Windsor, ONYou can travel by bus between Chicago, IL to Windsor, ON with Greyhound, FlixBus for as low as €35. 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
6h 10m
Cheapest Price
€40
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
7h 30m
Cheapest Price
€39
Greyhound frequency
3 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.
Complete guide to Windsor, ON
Things to do in Windsor, ON
Discover the best of Windsor, ON — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Windsor, ON trip today.
- Recommended
Chimczuk Museum
Local history museum inside the François Baby House, covering Windsor’s Indigenous, French, and borderland stories.
- Recommended
Canada South Science City
Hands-on science centre for families with interactive exhibits that make learning playful and accessible for children.
- Must visit
Windsor Riverfront Trail
Signature riverfront promenade with skyline views, gardens, public art, and one of Windsor’s best urban walks.
- Recommended
Festival Plaza
Lively downtown park and festival space hosting events, concerts, and seasonal gatherings beside the riverfront.
- Recommended
Riverside Park
Expansive waterfront park with lawns, paths, and broad Detroit River views, popular for relaxing and sunset walks.
Windsor-Style Pizza
Windsor-style pizza is the city’s signature pie, known for shredded pepperoni, canned mushrooms, Galati cheese, and often a sweeter sauce cut into squares.
Peameal Bacon Sandwich
A peameal bacon sandwich reflects Southwestern Ontario roots: cured cornmeal-coated pork on a bun, popular as a hearty local breakfast or lunch.
- Vegetarian
Poutine
Poutine is widely loved in Windsor, especially after nights out, with fries, cheese curds, and gravy served across diners, pubs, and takeaway spots.
The Carvery
Well-known Lebanese restaurant serving shawarma, grilled meats, salads, and fresh pita in a relaxed, family-friendly setting.
Antonino's Original Pizza
Iconic casual spot famous for classic Windsor-style pizza. Long-standing local favourite for takeout and informal dine-in.
Neros Steakhouse
Refined steakhouse by Caesars Windsor known for premium steaks, seafood, and polished service in an upscale dining room.
Canadian dollar ($)
Moderate for Canada. Hotels and dining are usually a bit cheaper than Toronto; transit is limited, so visitors may spend more on taxis or driving.
Average meal costs
- Budget
- $10-18 for fast food or casual takeaway.
- Mid-range
- $20-40 per person for a restaurant meal.
- Fine dining
- $60+ per person for upscale dining.
- Coffee
- $3-6 for coffee or cappuccino.
Tipping culture
Tip 15-20% at restaurants before or after tax, depending on the bill. Taxis usually get 10-15%. Cafes often have tip jars or card prompts, but small tips are optional.
FAQs: Bus from Chicago, IL to Windsor, ON
Find answers to the most common questions about traveling from Chicago, IL to Windsor, ON 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 Windsor, ON, this guide helps you travel smarter and with confidence.
Cheap bus tickets from Chicago, IL to Windsor, ON can start from as little as €39 when you book in advance. The average bus ticket price for Chicago, IL to Windsor, ON is €56 ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The average journey time by bus from Chicago, IL to Windsor, ON is 7h 30m to travel the 239 miles (386 km) long journey. Journey times can vary on weekends and holidays, so use our Journey Planner to search for a specific date.
The earliest bus from Chicago, IL to Windsor, ON leaves at 5:00 AM. Plan your trip with the Journey Planner from Omio.
The latest bus from Chicago, IL to Windsor, ON leaves at 11:55 PM.
There are 4 buses a day from Chicago, IL to Windsor, ON which require at least one change with Greyhound, FlixBus. Schedules can vary on holidays or weekends with fewer buses.
When taking a bus from Chicago, IL to Windsor, ON, you can count on Greyhound, FlixBus for the best way to get you to Windsor, ON. You can also check all possible bus companies who offer a service between Chicago, IL and Windsor, ON and compare the amenities they offer before buying a bus ticket.
A trip to Windsor, ON from Chicago, IL is worth doing but not as a day trip with a journey time of 7h 30m each way. Check with Omio app the best way to travel.
The cheapest month for a bus from Chicago, IL to Windsor, ON is December.
It's helpful to compare your options as there are 3 ways to travel between Chicago, IL and Windsor, ON including taking a bus, train, and flight.
Yes, the following accessibility options are available when taking the bus from Chicago, IL to Windsor, ON:
- Greyhound
- Assistance
- Priority seating
- Wheelchair-accessible buses.
- FlixBus
- Assistance
- Priority boarding
- Wheelchair-accessible buses.
Yes, there are bathrooms on board the bus from Chicago, IL to Windsor, ON for bus company Greyhound, FlixBus.
Whether you can cancel your bus ticket from Chicago, IL to Windsor, ON depends on the bus companies:
- 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.
Yes, bikes are allowed on board the bus with bus company Greyhound, FlixBus.
Tickets are often cheaper when booked early. Traveling during off-peak hours or on weekdays can help you save money. Sort results by price to quickly identify the most affordable options. Check for promotions or discounts available on our website and app.
Yes, there is food available to purchase on board the bus from Chicago, IL to Windsor, ON.
Yes, the following luggage options are included when booking a bus ticket from Chicago, IL to Windsor, ON:
- 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 Chicago, IL to Windsor, ON:
- Greyhound
- $15 per additional bag.
- FlixBus
- Additional luggage can be purchased for a fee.
Yes, you can bring your pet on the bus from Chicago, IL to Windsor, ON. The following conditions apply:
- FlixBus
- Small pets in carriers allowed
- guide dogs travel for free.
You can reserve your seat on the bus from Chicago, IL to Windsor, ON with the following bus company: Greyhound, FlixBus
Yes, there are USB plugs on board the bus from Chicago, IL to Windsor, ON with the following bus company: Greyhound, FlixBus.
Yes, there is Wifi on board the bus from Chicago, IL to Windsor, ON with the following bus company: Greyhound, FlixBus.
Since neither Chicago, IL nor Windsor, ON are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and Canada. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
We recommend using the train as it is the most popular way to get from Chicago, IL to Windsor, ON among Omio's users.
Canada uses the Canadian Dollar (CAD) as its currency. For travelers, using cards is generally more convenient and widely accepted across the country, including for transportation tickets, though carrying some cash can be useful for small vendors or remote areas.
In Windsor, ON, travelers should be cautious of petty theft, especially in crowded areas and public transit. Common scams include fake taxi services and inflated prices at some local vendors. It’s advisable to use licensed transportation and stay aware of surroundings, particularly near popular tourist spots and the waterfront.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
popular bus stations
Popular bus stations from Chicago, IL to Windsor, ON
Most Chicago, IL to Windsor, ON buses use the Chicago, Greyhound Bus Station to Windsor, Chatham St W (Windsor Transit Terminal) station pair. Use this guide to compare Chicago, IL and Windsor, ON bus stations on this route, check city-centre transport, alongside checking practicalities like bus station facilities and services.
Departure bus stations in Chicago
Arrival bus stations in Windsor
Chicago, Greyhound Bus Station
City-centre transport
Getting to Chicago, Greyhound Bus Station from Chicago city centre
Bus7 · 8m · €3 · every ~6 min
Chicago, Union Station (Amtrak)
City-centre transport
Getting to Chicago, Union Station (Amtrak) from Chicago city centre
Bus28, 151 · 7m · €3 · every ~13 min
Windsor, Chatham St W (Windsor Transit Terminal)Windsor Chatham St W, 300c Chatham St W, ON N9A
City-centre transport
Getting to Windsor, Chatham St W (Windsor Transit Terminal) from Windsor city centre
Bus1A, 1C · 16m · €3 · every ~13 min
1A, 1C · 18m · €3 · every ~13 min
Most popular bus connections from Chicago, IL
More options for your journey from Chicago, IL to Windsor, ON
Here are some other resources that might have the information you need
Most popular buses to and from Windsor, ON and Chicago, IL
Most popular bus connections to Windsor, ON
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