- Must visit
Art Institute of Chicago
One of the leading art museums in the world, known for Impressionist masterpieces, American art, and major rotating exhibitions.
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The cheapest and fastest buses from Windsor, ON to Chicago, IL
Showing times and prices for Jun 02
Cheapest price
$44
Average price
$56
Fastest journey
7 h 25 m
Average duration
8 h 38 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 $56 if you buy it on the day, but the cheapest tickets can be found for only $44.
Fast buses
Of the 4 buses that leave Windsor, ON for Chicago, IL on Tue, Jun 02, 4 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Tue, Jun 02 the direct buses cover the 386 km distance in an average of 8 h 38 m but if you time it right, some buses will get you there in just 7 h 25 m .
On Tue, Jun 02 the slowest buses will take 9 h 50 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.
10:00 AM7h25Windsor, ON5:25 PMChicago, IL$441One-way0 transfers- 9:00 AM7h25Windsor, ON4:25 PMChicago, IL$491One-way0 transfers
1:35 AM9h50Windsor, ON11:25 AMChicago, IL$581One-way0 transfers- 12:35 AM9h50Windsor, ON10:25 AMChicago, IL$731One-way0 transfers
- 10:00 AM7h25Windsor, ON5:25 PMChicago, IL$441One-way0 transfers
- 9:00 AM7h25Windsor, ON4:25 PMChicago, IL$491One-way0 transfers
- 1:35 AM9h50Windsor, ON11:25 AMChicago, IL$581One-way0 transfers
- 12:35 AM9h50Windsor, ON10:25 AMChicago, IL$731One-way0 transfers
Travel Information
Compare bus, train, and flight for Windsor, ON to Chicago, IL
Omio recommends booking the train as it is the most popular option from Windsor, ON to Chicago, IL among Omio's users. If you are prioritising price take the train with prices starting from $43. For those with little time consider booking a flight which can get you there in 4h 49m. The ticket price range depends on the travel mode: a train costs an average of $43, and a flight costs an average of $239.
Distance: 239 miles (386 km)
Compare bus with
| Bus | Most popular Train | Flight | Driving |
|---|---|---|---|
$62 Average price | $59 Average price Cheapest | $442 Average price | $95 Average price (fuel + tolls) |
9h 3m Average total duration 8h 33m Onboard + 30m Additional time* | 5h 56m Average total duration 5h 26m Onboard + 30m Additional time* | 7h 49m Average total duration Fastest 4h 49m Onboard + 3h 0m Additional time* | 4h 27m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
The cheapest way to travel from Windsor, ON to Chicago, IL is a train with an average price of $59 (€48).
This is compared to other travel options from Windsor, ON to Chicago, IL:
A train is $3 (€3) less than a bus for this route with tickets for a bus from Windsor, ON to Chicago, IL costing on average $62 (€51).
A train is $383 (€310) less than a flight for this route with tickets for a flight from Windsor, ON to Chicago, IL costing on average $442 (€357).
The fastest way to travel from Windsor, ON to Chicago, IL is by flight with an average journey time of 4h 49m.
Other travel options to Chicago, IL take longer:
Train takes on average 5h 26m.
Bus takes on average 8h 33m.
It's helpful to compare your options as there are 3 ways to travel between Windsor, ON and Chicago, IL including taking a bus, train, and flight.
We recommend using the train as it is the most popular way to get from Windsor, ON to Chicago, IL 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 $62 (€51) compared to roughly $95 (€77) in fuel and tolls — a saving of about $32 (€26). The journey takes 8h 33m versus 4h 27m 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.
Windsor, ON to Chicago, IL Bus Timetables
| Operator | Departure Time | Arrival Time | Duration | Departure days | Cheapest price |
|---|---|---|---|---|---|
Operator Greyhound | Departure Time 12:35AM | Arrival Time 10:25AM | Duration 9h50 | Departure days Wed, Thu, Fri | Cheapest price $65 |
Operator Greyhound | Departure Time 01:35AM | Arrival Time 11:25AM | Duration 9h50 | Departure days Wed, Fri, Sat | Cheapest price $53 |
Operator FlixBus | Departure Time 05:00AM | Arrival Time 11:25AM | Duration 7h25 | Departure days Sat | Cheapest price $67 |
Operator FlixBus | Departure Time 08:30AM | Arrival Time 05:35PM | Duration 10h05 | Departure days Sat | Cheapest price $67 |
Operator FlixBus | Departure Time 09:00AM | Arrival Time 04:25PM | Duration 7h25 | Departure days Tue | Cheapest price $49 |
Operator FlixBus | Departure Time 10:00AM | Arrival Time 05:25PM | Duration 7h25 | Departure days Tue | Cheapest price $44 |
Operator Greyhound | Departure Time 02:10PM | Arrival Time 09:25PM | Duration 8h15 | Departure days Sat | Cheapest price $67 |
Operator Greyhound | Departure Time 06:10PM | Arrival Time 02:25AM | Duration 8h15 | Departure days Mon, Wed, Thu, Fri | Cheapest price $47 |
Operator Greyhound | Departure Time 07:10PM | Arrival Time 03:25AM | Duration 8h15 | Departure days Mon, Wed, Thu, Fri, Sun | Cheapest price $54 |
Operator Greyhound | Departure Time 08:35PM | Arrival Time 05:25AM | Duration 9h50 | Departure days Sat | Cheapest price $67 |
Live departures
Windsor, ON to Chicago, IL bus times
The table below shows live departures for Windsor, ON to Chicago, IL buses for tomorrow, Tuesday, June 2. You can also manually refresh the results below to see updated bus journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 12:35 AM Windsor, ON | 9h50 | 10:25 AM Chicago, IL | 0 transfersDirect | |
| 1:35 AM Windsor, ON | 9h50 | 11:25 AM Chicago, IL | 0 transfersDirect | |
| 9:00 AM Windsor, ON | 7h25 | 4:25 PM Chicago, IL | 0 transfersDirect | |
| 10:00 AM Windsor, ON | 7h25 | 5:25 PM Chicago, IL | 0 transfersDirect | |
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, 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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Why should you book Windsor, ON to Chicago, IL buses with Omio?
Greyhound as well as FlixBus offer buses services from Windsor, ON to Chicago, IL.
Omio is an official ticket reseller for all your travel options from Windsor, ON to Chicago, IL.
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 Windsor, ON to Chicago, IL.
- 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 Windsor, ON to Chicago, IL.
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 Windsor, ON to Chicago, IL.
- Multiple modes of transport: Omio allows you to compare travel options including bus, train and flight to find the ideal travel option from Windsor, ON to Chicago, IL.
Journey information
Overview: Bus from Windsor, ON to Chicago, IL
Canada
USA
Buses from Windsor, ON to Chicago, IL run on average 3 times per day, taking around 8h 33m. Cheap bus tickets for this journey start at $41 (€33) if you book in advance.
The earliest bus runs at 05:00, the last at 23:55. The fastest bus covers the 239 miles (386 km) distance in 7h 25m.
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 8h 33m |
Cheapest ticket price $41 (€33) |
Buses per day 3 |
Fastest bus 7h 25m |
First bus 5:00 AM |
Last bus 11:55 PM |
Cheapest Month Sep |
Cheapest Day Mon |
High Season Jan - Mar |
Low Season Jul - Sep |
Busiest Day Thu |
Least Busy Day Thu |
Best time to book 7 days |
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: Greyhound, FlixBus from Windsor, ON to Chicago, ILYou can travel by bus between Windsor, ON to Chicago, IL with Greyhound, FlixBus for as low as $41 (€33). 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
7h 25m
Cheapest Price
$44 (€35)
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 15m
Cheapest Price
$41 (€33)
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.
Complete guide to Chicago
Things to do in Chicago
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
- Must visit
Field Museum
A top natural history museum famous for Sue the T. rex, global anthropology collections, and large-scale science exhibits.
- Must visit
Museum of Science and Industry
A large hands-on science museum with iconic exhibits including a captured German U-boat, trains, space, and engineering displays.
- Must visit
Millennium Park
Chicago's flagship downtown park, home to major public art, gardens, event spaces, and some of the city's busiest photo spots.
- Must visit
The Magnificent Mile
Famous stretch of North Michigan Avenue lined with historic towers, flagship stores, hotels, and classic city views.
- Must visit
Chicago Riverwalk
Popular pedestrian promenade along the river with excellent architecture views, bridges, and easy access to downtown attractions.
Deep-Dish Pizza
Chicago’s iconic thick-crust pizza baked in a deep pan with layers of cheese, toppings, and chunky tomato sauce.
Chicago-Style Hot Dog
An all-beef hot dog on a poppy seed bun topped with mustard, onions, relish, tomato, pickle spear, sport peppers, and celery salt.
Italian Beef Sandwich
A classic Chicago sandwich of thin-sliced seasoned beef served on a roll, often dipped in jus and topped with giardiniera or sweet peppers.
The Purple Pig
A well-known Magnificent Mile restaurant serving Mediterranean-influenced small plates, charcuterie, and strong wine selections.
Alinea
Chicago’s internationally acclaimed fine-dining restaurant known for inventive tasting menus and a polished, theatrical experience.
Lou Malnati's Pizzeria
A legendary Chicago pizzeria best known for buttery-crust deep-dish pizza in a casual, family-friendly setting.
United States Dollar
Moderate for a major U.S. city: casual food is reasonable, but hotels, downtown dining, and drinks can be pricey.
Average meal costs
- Budget
- USD 10-18 for fast food or casual takeout.
- Mid-range
- USD 25-45 per person at a mid-range restaurant.
- Fine dining
- USD 80+ per person before drinks and tip.
- Coffee
- USD 4-7 for a regular coffee or latte.
Tipping culture
Tip 18-20% at restaurants, 20%+ for great service. USD 1-2 per drink at bars, 10-15% for taxis, and a few dollars for hotel staff.
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 $62 (€51) ; 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 Windsor, ON to Chicago, IL is 7h 25m 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 Windsor, ON to Chicago, IL leaves at 5:00 AM. Plan your trip with the Journey Planner from Omio.
The latest bus from Windsor, ON to Chicago, IL leaves at 11:55 PM.
There are 3 buses a day from Windsor, ON to Chicago, IL which require at least one change with Greyhound, FlixBus. Schedules can vary on holidays or weekends with fewer buses.
When taking a bus from Windsor, ON to Chicago, IL, you can count on Greyhound, FlixBus for the best way to get you to Chicago, IL. You can also check all possible bus companies who offer a service between Windsor, ON and Chicago, IL and compare the amenities they offer before buying a bus ticket.
A trip to Chicago, IL from Windsor, ON is worth doing but not as a day trip with a journey time of 7h 25m each way. Check with Omio app the best way to travel.
The cheapest month for a bus from Windsor, ON to Chicago, IL is September.
It's helpful to compare your options as there are 3 ways to travel between Windsor, ON and Chicago, IL including taking a bus, train, and flight.
Yes, there are bathrooms on board the bus from Windsor, ON to Chicago, IL for bus company Greyhound, FlixBus.
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.
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.
Whether you can cancel your bus ticket from Windsor, ON to Chicago, IL 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 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 company: Greyhound, FlixBus
Yes, there are USB plugs on board the bus from Windsor, ON to Chicago, IL with the following bus company: Greyhound, FlixBus.
Yes, there is Wifi on board the bus from Windsor, ON to Chicago, IL with the following bus company: Greyhound, FlixBus.
Since neither Windsor, ON nor Chicago, IL are in the Schengen Area, passport requirements depend on the specific immigration rules of Canada and United States. 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 Windsor, ON to Chicago, IL among Omio's users.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Chicago, IL, travelers should be cautious of pickpocketing and purse snatching, especially in crowded areas like public transit and popular tourist spots. Common scams include fake charity solicitations and distraction thefts. It is advisable to stay alert in neighborhoods outside downtown after dark and use authorized transportation services to avoid unlicensed taxi scams. Keeping valuables secure and being aware of surroundings helps mitigate these risks.
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 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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