Winnipeg to Chicago, IL from undefined1815: 10 ways by bus, train, flight or car

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

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$1815 - DriveBest price

1397 kmDistance

5h 36m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Winnipeg 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.

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Traveling From Winnipeg to Chicago

Traveling from Winnipeg to Chicago offers a striking contrast between the serene, scenic landscapes of Canada and the vibrant, bustling city life of the Windy City.

Best Neighbourhoods in Chicago

Chicago’s neighborhoods each offer distinct experiences and local charm.

Wicker Park

• Trendy shops and art galleries abound.

• Vibrant nightlife with unique bars and restaurants.

Lincoln Park

• Home to beautiful parks and the Lincoln Park Zoo.

• Upscale dining and shopping options throughout.

The Loop

• Central business district filled with iconic skyscrapers.

• Easy access to museums, theaters, and public transport.

Best Times To Visit Chicago's Attractions

Visiting Chicago’s attractions can be a breeze with the right timing.

Millennium Park

Early mornings or weekdays offer a peaceful vibe and fewer visitors.

The Art Institute of Chicago

Visit during late afternoons on weekdays for a quieter experience.

Navy Pier

Go in the evening during weekdays to enjoy the views without the rush.

Chicago Weather: What to Expect Year-Round

Chicago experiences a humid continental climate, with distinct seasons that include hot summers and cold winters; the best times to visit are typically late spring and early fall for mild temperatures. Weather conditions can significantly impact your travel experience, as snow in winter may limit some activities, while summer heat brings vibrant festivals and outdoor events.

Dining Recommendation in Chicago

When in Chicago, indulge in a deep-dish pizza at Lou Malnati's, where the rich, buttery crust and layers of gooey cheese create a hearty dining experience that’s a far cry from Winnipeg’s more straightforward offerings. The lively atmosphere and focus on fresh, local ingredients give Chicago's culinary scene a unique flair that sets it apart, inviting you to savor every bite.

Winnipeg - Chicago operators

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

Plane Show flights

Website

united.com

Plane from Winnipeg Airport (YWG) to Chicago O'Hare Airport (ORD)

Average Duration

2h 28m

Estimated price

12289-3030

Plane from Winnipeg Airport (YWG) to Chicago O'Hare Airport (ORD) via Toronto

Average Duration

5h 56m

Estimated price

3031-3032

Plane from Winnipeg Airport (YWG) to South Bend Airport (SBN) via Chicago O'Hare

Average Duration

4h 31m

Estimated price

3033-12288

Plane from Winnipeg Airport (YWG) to Milwaukee Airport (MKE) via Chicago O'Hare

Average Duration

4h 47m

Estimated price

3036-12288

Website

delta.com

Plane from Winnipeg Airport (YWG) to Chicago O'Hare Airport (ORD) via Minneapolis

Average Duration

4h 14m

Estimated price

1817-12281

Plane from Winnipeg Airport (YWG) to Chicago Midway Airport (MDW) via Atlanta

Average Duration

9h 1m

Estimated price

12284-12285

Website

aircanada.com

Plane from Winnipeg Airport (YWG) to Chicago O'Hare Airport (ORD)

Average Duration

2h 28m

Estimated price

12289-3030

Plane from Winnipeg Airport (YWG) to Chicago O'Hare Airport (ORD) via Toronto

Average Duration

5h 51m

Estimated price

3031-3032

Train Show train routes

Contact phone

+1 800-872-7245

Website

amtrak.com

Train from Winnipeg to Chicago Union Station

Average Duration

54h 6m

Estimated price

0-0

Train from Toronto Union Station to Windsor

Average Duration

4h 18m

Estimated price

22715-1858

Train from Toronto Union Station to London

Average Duration

2h 16m

Estimated price

15265-15260

Train from Buffalo Depew Station to Chicago Union Station

Average Duration

10h 33m

Estimated price

2273-22780

Contact phone

+1 888 842-7245

Website

viarail.ca

Train from Winnipeg to Toronto Union Station

Average Duration

37h 59m

Estimated price

12282-1857

Bus

Contact phone

+1 705 472 4500

Website

ontarionorthland.ca

Bus from Winnipeg to Thunder Bay

Average Duration

8h 49m

Estimated price

1856-15269

Bus from Thunder Bay to Sault Ste Marie

Average Duration

9h 47m

Estimated price

15267-12282

Contact phone

+1 214-849-8100

Website

greyhound.com

Bus from Kalamazoo Bus Stop to Chicago Bus Station

Average Duration

2h 55m

Estimated price

14120-1854

Bus from Detroit Bus Station to Chicago Bus Station

Average Duration

7h 5m

Estimated price

22710-1852

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

Traveling between Winnipeg 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 Winnipeg to the vibrant city of Chicago covering a distance of 868 miles in approximately 14 hours and 23 minutes. Enjoy the changing landscapes and charming towns along the way as you make your way south. 💰 The cost of driving from Winnipeg to Chicago by car can range from C$257 to C$392, depending on factors like gas prices, tolls, and potential overnight stays. Plan your budget accordingly to ensure a smooth journey with no financial surprises.

Average price

C$262 - C$400

🌆 The trip includes transfers at Toronto Union Station and Buffalo Depew Station before arriving at Chicago Union Station. The total duration of the journey, with transfers, is approximately 2 days and 6 hours. 💰 Ticket prices for the train from Winnipeg to Chicago range from C$269 to C$577. This adventure by train offers a unique and leisurely way to travel between these two vibrant cities.

Departure Point

Winnipeg station

Arrival Point

Chicago Union Station

🛫 Flying from Winnipeg to Chicago is a convenient option, with the quickest direct flight taking just 2 hours and 28 minutes. 💰 Depending on the airline and time of booking, the prices for flights between Chicago and Winnipeg can range from C$181 to C$1225, making it essential to plan ahead for the best deals.

Departure Point

Winnipeg Airport

Arrival Point

Chicago O'Hare Airport

Frequently asked questions

Find out more about the route from Winnipeg to Chicago.

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The distance between Winnipeg and Chicago is approximately 721 miles or 868.3 road miles. Travel times vary depending on the mode of transportation. By train, it takes about to reach Chicago from Winnipeg. By taking a flight to South Bend and then a train, the travel time is approximately 13 hours and 38 minutes. By plane, it takes around 7 hours and 58 minutes to reach Chicago from Winnipeg. To drive from Chicago to Winnipeg, the travel time is about 14 hours and 23 minutes.

The most cost-effective option for traveling from Winnipeg to Chicago is to drive, as it is cheaper compared to other modes of transportation. However, driving takes the longest time, with a travel duration of 14 hours and 23 minutes. For a more time-efficient option, flying is the quickest choice, with a travel time of 7 hours and 2 minutes. Although it may be more expensive, flying allows for a much faster journey.

The prices for a train ticket between Winnipeg and Chicago range from C$265 to C$572. The exact price depends on factors such as the class of ticket and availability. It is recommended to check with various train operators or travel agencies to find the best price and deals for this journey.

To travel from Winnipeg to Chicago without using public transportation, you can drive. The road distance between the two cities is 868 miles, and it takes approximately 14 hours and 23 minutes to drive from Winnipeg to Chicago. Keep in mind that the prices for a car trip vary, ranging from C$256 to C$390.

To travel from Winnipeg to Chicago without a car, the best option is to take a combination of train and bus. This journey takes approximately 2 days and 5 hours and costs around C$256 to C$592. Alternatively, you can fly from Winnipeg to Chicago which takes about 7 hours and 58 minutes and costs between C$256 and C$942. Another option is to take a combination of bus and Amtrak Thruway operated by Indian Trails, which takes about 34 hours and 54 minutes. Train travel is also an option, taking approximately 2 days and 2 hours and costing between C$256 and C$578.

No, there is no direct train link between Winnipeg and Chicago. However, there are alternative routes available with transfers. The journey typically takes approximately 2 days and 7 hours, involving transfers at Toronto Union Station and Buffalo Depew Station. The train services are operated by VIA Rail and Amtrak.

The flight duration between Winnipeg and Chicago varies depending on the number of stopovers. The quickest flight with one stopover takes approximately 4 hours and 49 minutes. However, please note that there are no direct flights available for this route. The cost of a flight between Chicago and Winnipeg can range from C$261 to C$884, depending on factors such as airline, time of booking, and class of service. It is advisable to check with different airlines and compare prices to find the best deal for your travel needs.

There are a variety of accommodations available in Chicago, with over 1,116 hotels to choose from. Prices start at C$78 per night, offering options for various budgets. Whether you prefer luxury hotels, boutique accommodations, or budget-friendly options, there is something to suit every traveler's preference near Chicago. It is recommended to research and book in advance to secure the best rates and availability.

Winnipeg to Chicago, IL from undefined1815: 10 ways by bus, train, flight or car

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

Compare Train, Bus, Flight, and Driving Options

See more options

Traveling From Winnipeg to Chicago

Best Neighbourhoods in Chicago

Best Times To Visit Chicago's Attractions

Chicago Weather: What to Expect Year-Round

Dining Recommendation in Chicago

Winnipeg - Chicago operators

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

Frequently asked questions

Trips from Winnipeg

Trips to Chicago

Popular routes