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Chicago, IL, USA to Windsor from $12: 9 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Chicago, United States of America
to
Windsor, Canada

How to Get from Chicago to Windsor: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$12 by trainBest price
386 kmDistance
3h 55m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Chicago to Windsor with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
Amtrak
Train
Average Duration
5h  43m
Estimated price
$12-122
Recommended
Company
Amtrak
Train
Average Duration
5h  43m
Estimated price
$12-125
Cheapest
route map
Distance: 386 km
Duration: 3h 55m

See more options

Company
Greyhound
Bus
Average Duration
6h 
Estimated price
$26-90
Company
Various
Plane
Average Duration
4h  24m
Estimated price
$32-387
Company
Various
Drive
Average Duration
4h  45m
Estimated price
$65-95
Company
Various
Drive
Average Duration
4h  8m
Estimated price
$120-121
Company
Various
Drive
Average Duration
4h  4m
Estimated price
$122-123
Company
Various
Plane
Average Duration
5h  32m
Estimated price
$122-124
Company
Various
Plane
Average Duration
3h  55m
Estimated price
$228-234
Browse car rentalsExplore flights

Traveling From Chicago to Windsor

The journey from Chicago, bustling with urban energy and iconic architecture, to Windsor, known for its serene riverside views and charming small-town vibe, offers a fascinating contrast in experiences.

Best Neighbourhoods in Windsor

Windsor features diverse neighborhoods, each offering unique experiences to explore.

Walkerville
• Known for its historic architecture.
• Home to local breweries and artisan shops.
Downtown Windsor
• Vibrant nightlife and entertainment options.
• Scenic waterfront parks along the Detroit River.
Riverside
• Picturesque views of the river and Detroit skyline.
• Great for leisurely walks and outdoor activities.

Best Times To Visit Windsor's Attractions

Timing can elevate your experience at Windsor's must-see spots.

Canadian Club Brand Centre
Midweek visits offer a quieter atmosphere and more personalized tours.
Windsor Sculpture Park
Early mornings provide peaceful strolls and perfect photo opportunities.
Dieppe Gardens
Visit during weekdays to fully enjoy the garden’s tranquility.

Windsor Weather: What to Expect Year-Round

Windsor experiences a humid continental climate, characterized by warm summers and cold winters, making spring and early fall ideal for pleasant excursions. Being mindful of seasonal weather patterns can enhance your travel plans, whether you're enjoying summer festivals or exploring winter festivities.

Dining Recommendation in Windsor

For a unique culinary experience, try the classic Canadian dish of peameal bacon sandwich at The Cook’s Shop, where the cozy atmosphere and locally sourced ingredients create a welcoming vibe. This contrasts with Chicago's bustling food scene, offering a simpler yet flavorful taste that celebrates Windsor's cultural heritage.

Chicago - Windsor operators

Explore transport companies operating between Chicago and Windsor, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Train Show train routes
Contact phone
+1 800-872-7245
Website
https://www.amtrak.com/home.html

Train from Chicago Union Station to Dearborn

Average Duration
4h 54m
Estimated price
$120-128

Train from Chicago Union Station to Milwaukee

Average Duration
1h 29m
Estimated price
$650-909
Bus Show bus routes
Contact phone
+1 214-849-8100
Website
https://www.greyhound.com/

Bus from Chicago Bus Station to Detroit Bus Station

Average Duration
6h
Estimated price
$129-260
Contact phone
+1 (855) 626-8585
Website
https://www.flixbus.com/

Bus from Chicago Bus Station to Detroit Bus Station

Average Duration
5h 10m
Estimated price
$26-90
Plane Show flights
Website
https://www.delta.com/

Plane from Chicago Midway to Detroit

Average Duration
1h 7m
Estimated price
$261-262

Plane from Chicago O'Hare to Detroit

Average Duration
1h 21m
Estimated price
$261-262
Website
https://www.southwest.com/

Plane from Chicago Midway to Detroit

Average Duration
1h 6m
Estimated price
$900-1220
Website
https://www.aa.com/

Plane from Chicago O'Hare to Detroit

Average Duration
1h 29m
Estimated price
$2630-266
Website
https://www.united.com/

Plane from Chicago O'Hare to Detroit

Average Duration
1h 25m
Estimated price
$2630-266

Chicago to Windsor: Overview of Bus, Train, Flight, and Car Trips

Traveling between Chicago and Windsor offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🚗 Embark on a scenic road trip from Chicago to Windsor, covering a distance of 286 miles. Taking around 4 hours and 45 minutes, the journey promises beautiful landscapes and smooth highways. 💸 Depending on factors such as gas prices and tolls, the cost of driving from Chicago to Windsor typically ranges between $65 to $95. Make sure to budget accordingly for a comfortable and enjoyable ride.
Average price
$65 - $95
🚅 Embark on a scenic train journey from Chicago to Windsor that takes approximately 5 hours and 43 minutes. Enjoy a comfortable ride while taking in the beauty of the landscapes along the way. 💵 The prices for a train ticket from Chicago to Windsor range from $12 to $122, offering travelers a range of options to suit their budget and preferences. Choose from different classes and amenities to enhance your travel experience.
🛫 Flying from Chicago to Windsor involves taking a direct 1 hour and 5-minute flight from Chicago Midway Airport to Detroit Airport. Both Delta and Southwest Airlines operate flights on this route. 🛄 After arriving in Detroit, travelers will have a layover before boarding a connecting flight to Windsor. The total travel time from Chicago to Windsor by plane is approximately 3 hours and 55 minutes. 💸 Prices for flights between Windsor and Chicago typically range from $228 to $234, depending on the airline, time of booking, and other factors. It's recommended to compare different options to find the best deal for your trip.
Departure Point
Chicago Midway Airport
Arrival Point
Detroit Airport
🌇 Services operate three times a day and run every day, making it easy to plan your trip and choose a suitable departure time. The journey typically takes approximately 6 hours, allowing for a comfortable and efficient travel experience. 💸 Prices for the bus ticket between Windsor and Chicago can range from $26 to $90, providing flexibility for different budgets and travel preferences. Enjoy the scenic route and hassle-free transportation as you make your way from the bustling city of Chicago to the charming city of Windsor.
Departure Point
Chicago Bus Station
Arrival Point
Detroit Bus Station

Frequently asked questions

Find out more about the route from Chicago to Windsor.

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The distance between Chicago and Windsor is 240 miles. The typical travel time from Chicago to Windsor varies depending on the mode of transportation chosen. By train, it takes approximately 5 hours and 43 minutes. Taking a flight from Chicago O'Hare to Flint and then a bus from Flint to Windsor takes about 5 hours and 51 minutes. Flying directly from Chicago to Windsor takes around 3 hours and 47 minutes. If driving, it takes about 4 hours and 45 minutes, while taking a bus from Chicago to Windsor takes around 7 hours.
The most cost-effective and time-efficient transportation options for traveling from Chicago to Windsor are by bus or by plane. Taking the bus is the cheapest option, with prices ranging from $24 to $160 and a travel time of approximately 7 hours. However, if time is a priority, flying would be the quickest option, taking only 3 hours and 47 minutes with prices ranging from $65 to $370. Considering both cost and time, it is recommended to choose the option that best suits your personal preferences and needs.
The prices for a train ticket between Chicago and Windsor range from $12 to $122, depending on factors such as class and availability. On the other hand, the prices for a bus ticket between Windsor and Chicago can range from $24 to $160, depending on the bus company and type of service. It's important to compare prices and book in advance to get the best deal for your travel from Chicago to Windsor or vice versa.
To travel from Chicago to Windsor without using public transportation, you can opt to drive. The road distance is 286 miles, and it typically takes around 4 hours and 45 minutes to drive from Chicago to Windsor. Renting a car or using your own vehicle would provide flexibility and convenience during the journey. The cost of car rental varies, with prices ranging from $65 to $95, depending on the rental agency and the type of vehicle chosen.
To travel from Chicago to Windsor without a car, the best option is to take a train. The train journey takes approximately 5 hours and 43 minutes and costs between $12 and $130. Another option is to take a bus, which takes around 7 hours and costs between $24 and $160. Alternatively, flying is also an option, with a flight duration of 3 hours and 47 minutes and a cost ranging from $65 to $370. Choose the mode of transportation that best suits your budget and time preference.
Yes, there is a direct link between Chicago and Windsor. Indian Trails operates a bus service that departs from Chicago and arrives at Detroit, MI. The journey takes approximately 7 hours and operates four times a day, every day. This provides a convenient and direct option for travel between the two cities.
The flight between Chicago and Windsor typically takes around 1 hour. However, it's important to note that this is the duration of the direct flight from Chicago Midway Airport to Detroit Airport, which is the closest airport to Windsor. The cost of the flight can vary, ranging from $68 to $367, depending on the airline, time of booking, and other factors.
There are plenty of options for accommodation near Windsor. With over 277 hotels to choose from, you can find a range of options to suit different budgets and preferences. Prices for hotels in Windsor start at around $60 per night, so there are options available for those looking for affordable stays. From budget-friendly options to luxury hotels, visitors to Windsor will have a variety of choices to accommodate their needs.

Trips from Chicago