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Windsor to Chicago, IL from undefined16: 7 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Windsor, Canada
to
Chicago, United States of America

How to Get from Windsor to Chicago: 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.

$16 by trainBest price
386 kmDistance
3h 26m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Windsor to Chicago 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
Southwest Airlines, Delta
Plane
Average Duration
3h  37m
Estimated price
97-510
Recommended
Company
Amtrak
Train
Average Duration
6h  41m
Estimated price
16-162
Cheapest
route map
Distance: 386 km
Duration: 3h 26m

See more options

Company
Greyhound
Bus
Average Duration
7h  5m
Estimated price
35-122
Company
various
Plane
Average Duration
4h 
Estimated price
92-375
Company
various
Drive
Average Duration
3h  26m
Estimated price
133-363
Company
various
Bus
Average Duration
7h  25m
Estimated price
970-165
Company
various
Drive
Average Duration
4h  45m
Estimated price
971-972
Browse car rentalsExplore flights

Traveling From Windsor to Chicago

The journey from Windsor to Chicago showcases a fascinating contrast, with Windsor's charming riverside tranquility offering a serene escape, while Chicago's vibrant urban energy pulses with lively culture and iconic landmarks.

Best Neighborhoods in Chicago

Chicago’s neighborhoods are vibrant and diverse, each offering a distinct character.

Wicker Park
• Known for its trendy boutiques and cafes.
• A hub for live music and nightlife.
Lincoln Park
• Features beautiful parks and the Lincoln Park Zoo.
• Offers a mix of cultural attractions and dining options.
The Loop
• Home to iconic skyscrapers and Millennium Park.
• Great access to museums, shopping, and dining.

Best Times To Visit Chicago's Attractions

Timing your visits to Chicago's attractions can greatly enhance your experience.

Millennium Park
Visit early morning on weekdays to enjoy fewer crowds and tranquility.
The Art Institute of Chicago
Plan for late afternoons during weekdays for a more relaxed atmosphere.
Navy Pier
Go on weekdays in the late afternoon to avoid the weekend rush.

Chicago Weather: What to Expect Year-Round

Chicago experiences a diverse climate with cold winters and warm summers, making spring and fall the ideal times for comfortable exploration. Understanding the weather can help you pack appropriately and plan your activities, ensuring a more enjoyable travel experience.

Dining Recommendation in Chicago

Try the deep-dish pizza at Lou Malnati's, an iconic Chicago staple known for its buttery crust and rich, savory toppings that stand in stark contrast to Windsor's more classic fare. The lively atmosphere and distinct use of local ingredients elevate your dining experience, offering a bold taste of Chicago's culinary identity.

Windsor - Chicago operators

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

Plane Show flights
Website
southwest.com

Plane from Detroit (DTW) to Chicago Midway (MDW)

Average Duration
1h 12m
Estimated price
97-510
Website
delta.com

Plane from Detroit (DTW) to Chicago Midway (MDW)

Average Duration
1h 17m
Estimated price
97-510

Plane from Detroit (DTW) to Chicago O'Hare (ORD)

Average Duration
1h 25m
Estimated price
9730-5105
Website
united.com

Plane from Detroit (DTW) to Chicago O'Hare (ORD)

Average Duration
1h 32m
Estimated price
9730-978

Plane from Flint (FNT) to Chicago O'Hare (ORD)

Average Duration
1h 35m
Estimated price
979-5100
Train Show train routes
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from Dearborn to Chicago Union Station

Average Duration
5h 11m
Estimated price
16-162
Bus Show bus routes
Contact phone
+1 214-849-8100
Website
greyhound.com

Bus from Detroit Bus Station to Chicago Bus Station

Average Duration
7h 5m
Estimated price
35-122

Bus from Detroit, MI to South Street Station - South Bend

Average Duration
1h 40m
Estimated price
166-5106

Bus from South Bend Transpo to Chicago Bus Station

Average Duration
1h 40m
Estimated price
166-5106
Contact phone
+1 (855) 626-8585
Website
flixbus.com

Bus from Detroit Bus Station to Chicago Bus Station

Average Duration
5h 10m
Estimated price
35-122
Contact phone
+1 800-544-2383
Website
hoosierride.com
Contact phone
+1 888-378-3823
Website
baronsbus.com

Bus from South Bend, IN to Chicago

Average Duration
1h 45m
Estimated price
167-5106

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

Traveling between Windsor and Chicago 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 Windsor to Chicago, covering a distance of 286 miles. Enjoy around 4 hours and 45 minutes of picturesque drive through the diverse landscapes of Ontario and Illinois. 💰 Exploreeconomical options for the journey, as prices to reach Chicago from Windsor by car range from C$88 to C$128. Choose from various routes and plan your budget-friendly adventure accordingly.
Average price
C$90 - C$131
🚆 Embark on a scenic train journey from Windsor to Chicago lasting approximately 6 hours and 41 minutes. Relax and enjoy the views as you travel through the beautiful Great Lakes region. 💸 Ticket prices for the train ride between Windsor and Chicago range from C$16 to C$162, offering a range of options to suit different budgets. Whether you opt for a standard seat or a more luxurious class, the journey promises a comfortable and enjoyable experience.
🛫 Experience a convenient journey from Windsor to Chicago by taking a quick 1 hour and 5 minute direct flight from Detroit Airport to Chicago Midway Airport with airlines like Delta and Southwest Airlines. 🏙️ Enjoy a smooth and efficient travel experience as you cover the distance of 3 hours and 37 minutes from Windsor to Chicago. With multiple flights available, you can easily find a suitable option that fits your schedule. 💸 Prices for flights between Chicago and Windsor range from C$97 to C$509, offering travelers a range of choices to suit their budget and travel preferences. Plan your trip ahead and secure your flight booking for a hassle-free journey.
Departure Point
Detroit Airport
Arrival Point
Chicago Midway Airport
🚌 The bus journey from Windsor to Chicago starts at the Detroit Bus Station and ends at the Chicago Bus Station, with departures occurring four times daily. The ride takes approximately 7 hours and 5 minutes. 🚌 Greyhound USA operates the Windsor to Chicago bus services, making it a convenient and reliable transportation option. The buses run every day, offering travelers flexibility in their schedules for the 7-hour journey through scenic routes. 🚌 Travelers can expect ticket prices for the Windsor to Chicago bus to range from C$35 to C$122, providing an affordable and comfortable way to explore the vibrant city of Chicago from the charming town of Windsor.
Departure Point
Detroit Bus Station
Arrival Point
Chicago Bus Station

Frequently asked questions

Find out more about the route from Windsor to Chicago.

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The distance between Windsor and Chicago is approximately 240 miles by air. The quickest mode of transportation is by plane, with a typical travel time of 3 hours and 38 minutes. Alternatively, if you prefer to travel by train, it would take around 6 hours and 40 minutes. By car, the travel time is approximately 4 hours and 45 minutes, while taking a bus can take around 7 hours and 5 minutes.
The most cost-effective option for traveling from Windsor to Chicago is by bus via 95th, which takes approximately 7 hours and 7 minutes and costs between C$33 and C$214. This mode of transportation allows for a budget-friendly journey but may take longer. However, if time efficiency is a priority, flying is the quickest option, taking around 3 hours and 38 minutes and costing between C$87 and C$494. Flying allows travelers to reach their destination swiftly but may be more expensive than taking the bus.
The prices for traveling from Windsor to Chicago by train range from C$16 to C$162. The cost of a bus ticket from Chicago to Windsor can range from C$32 to C$214. It is advisable to compare prices and book in advance to secure the best deal for your travel needs.
To travel from Windsor to Chicago without using public transportation, you can choose to drive. The distance between Windsor and Chicago is approximately 286 miles, and it takes around 4 hours and 45 minutes to drive between the two cities. The driving route offers flexibility and the price for a car rental varies from C$87 to C$127.
To travel from Windsor to Chicago without a car, the best option is by train, which takes approximately 6 hours and 40 minutes and costs between C$15-C$174. Another option is to fly, which takes about 3 hours and 38 minutes and costs between C$87-C$494. If you prefer, you can also take a bus, which takes around 7 hours and 5 minutes and costs between C$32-C$214. These modes of transportation provide convenient and affordable options for traveling from Windsor to Chicago without a car.
Yes, there is a direct link between Windsor and Chicago. Greyhound USA operates a bus service that departs from Detroit Bus Station and arrives at Chicago Bus Station. The journey takes approximately 7 hours and 5 minutes. The buses run five times a day and operate every day, providing a convenient and direct transportation option between Windsor and Chicago.
The flight between Windsor and Chicago typically takes around 1 hour and 5 minutes. The quickest route is a direct flight from Detroit Airport to Chicago Midway Airport. The cost of a flight between Chicago and Windsor can vary between C$91 and C$490. Prices may vary depending on factors such as airline, class of travel, and timing.
There are plenty of accommodation options in Chicago with over 1116 hotels to choose from. Prices for hotels start at C$77 and range to suit different budgets and preferences. Whether you are looking for luxury hotels, boutique accommodations, or budget-friendly options, there is something for everyone in Chicago. It is advisable to book your hotel in advance to secure the best deals and availability.

Trips from Windsor

Trips to Chicago