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Chicago, IL, USA to Winnipeg from $136: 9 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Chicago, United States of America
to
Winnipeg, Canada

How to Get from Chicago to Winnipeg: 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.

$136 - PlaneBest price
1396 kmDistance
5h 46m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Chicago to Winnipeg 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
various
Plane
Average Duration
5h  46m
Estimated price
$206-608
Recommended
Company
various
Plane
Average Duration
7h  55m
Estimated price
$136-608
Cheapest
route map
Distance: 1396 km
Duration: 5h 46m

See more options

Company
various
Bus
Train
Bus
Average Duration
35h  6m
Estimated price
$0-0
Company
various
Train
Average Duration
46h  35m
Estimated price
$198-434
Company
various
Train
Plane
Average Duration
10h  36m
Estimated price
$199-767
Company
various
Train
Plane
Average Duration
9h  13m
Estimated price
$269-743
Company
various
Bus
Bus
Train
Average Duration
48h 
Estimated price
$2060-2061
Company
various
Train
Average Duration
50h  3m
Estimated price
$2062-2063
Company
N/A
Drive
Average Duration
14h  22m
Estimated price
$2064-2065
Browse car rentalsExplore flights

Traveling From Chicago to Winnipeg

Your journey from the bustling streets of Chicago to the serene landscapes of Winnipeg offers a striking contrast between urban energy and Canadian charm.

Best Neighbourhoods in Winnipeg

Winnipeg boasts diverse neighborhoods, each offering distinct experiences for visitors.

The Forks
• Historic site with markets and parks.
• Stunning riverside views and walkways.
Osborne Village
• Vibrant arts scene with local shops.
• Popular dining spots and nightlife options.
Exchange District
• Rich in heritage buildings and culture.
• Home to unique galleries and theaters.

Best Times To Visit Winnipeg's Attractions

Timing your visits can enhance your experience at Winnipeg's attractions.

The Canadian Museum for Human Rights
Visit on weekdays early in the morning for a quieter experience.
Assiniboine Park
Explore during spring or early fall for fewer crowds and beautiful scenery.
The Forks Market
Go on a weekday afternoon to enjoy local vendors with less hustle.

Winnipeg Weather: What to Expect Year-Round

Winnipeg experiences a continental climate with hot summers and frigid winters, making your travel experience highly seasonal. The best times to visit are late spring and early fall, when mild temperatures and vibrant surroundings enhance outdoor activities.

Dining Recommendation in Winnipeg

Indulge in Winnipeg's signature dish, bison sliders, at the charmingly rustic restaurant, The Forks Market. This culinary experience features locally sourced ingredients and a cozy atmosphere, offering a delightful contrast to Chicago’s fast-paced dining scene.

Chicago - Winnipeg operators

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

Plane Show flights
Website
united.com

Plane from Chicago O'Hare to Winnipeg

Average Duration
2h 26m
Estimated price
$1364-1365

Plane from Chicago O'Hare to Winnipeg via Toronto

Average Duration
5h 22m
Estimated price
$1364-6088

Plane from Milwaukee to Winnipeg via Chicago O'Hare

Average Duration
5h
Estimated price
$1366-1367

Plane from South Bend to Winnipeg via Chicago O'Hare

Average Duration
6h 59m
Estimated price
$2064-6088
Website
delta.com

Plane from Chicago O'Hare to Winnipeg via Minneapolis

Average Duration
4h 58m
Estimated price
$6080-6081

Plane from Chicago Midway to Winnipeg via Minneapolis

Average Duration
5h 25m
Estimated price
$6082-6083

Plane from Chicago Midway to Winnipeg via Atlanta

Average Duration
8h 55m
Estimated price
$2066-6084

Plane from Chicago Midway to Winnipeg via Detroit, Minneapolis

Average Duration
10h 22m
Estimated price
$6085-6086
Website
aircanada.com

Plane from Chicago O'Hare to Winnipeg

Average Duration
2h 26m
Estimated price
$1364-1365

Plane from Chicago O'Hare to Winnipeg via Toronto

Average Duration
5h 22m
Estimated price
$1364-6088

Plane from Milwaukee to Winnipeg via Chicago O'Hare

Average Duration
5h
Estimated price
$1366-1367

Plane from South Bend to Winnipeg via Chicago O'Hare

Average Duration
6h 59m
Estimated price
$2064-6088
Train Show train routes
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from Chicago Union Station to Milwaukee

Average Duration
1h 29m
Estimated price
$1368-1369

Train from Chicago Union Station to Buffalo Depew Station

Average Duration
10h 23m
Estimated price
$2690-6087

Train from Chicago Union Station to Dearborn

Average Duration
4h 54m
Estimated price
$2698-2699

Train from Chicago Union Station to Toronto Union Station

Average Duration
34h 35m
Estimated price
$1366-6082
Contact phone
+1 888-842-7245
Website
viarail.ca

Train from Windsor to Toronto Union Station

Average Duration
4h 9m
Estimated price
$13685-1992

Train from Toronto Union Station to Winnipeg

Average Duration
34h 35m
Estimated price
$1366-6082
Bus
Contact phone
+1 214-849-8100
Website
greyhound.com

Bus from Chicago Bus Station to Kalamazoo Bus Stop

Average Duration
2h 50m
Estimated price
$1994-7439

Bus from Kalamazoo, MI - Amtrak to Sault Sainte Marie Amtrak Bus Stop

Average Duration
10h 15m
Estimated price
$0-0
Contact phone
+1 705 472 4500
Website
ontarionorthland.ca

Bus from Sault Ste Marie to Thunder Bay

Average Duration
10h
Estimated price
$7434-1366

Bus from Thunder Bay to Winnipeg

Average Duration
8h 49m
Estimated price
$7437-7436

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

Traveling between Chicago and Winnipeg 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 Winnipeg covering a distance of 867 miles. The journey offers a mix of urban landscapes and tranquil countryside views along the way. 💰 Budget-conscious travelers can expect car trip costs ranging from $190 to $290 for the entire journey from Chicago to Winnipeg. With careful planning, you can make the most of your travel budget while enjoying the scenic route and diverse attractions awaiting in Winnipeg. ⏱️ Set aside around 14 hours and 22 minutes for this exciting road adventure from Chicago to Winnipeg. Prepare to make pit stops, explore charming towns en route, and create lasting memories as you traverse the miles towards your Canadian destination.
Average price
$190 - $290
💵 The ticket prices for the Chicago to Winnipeg train range from $198 to $434, offering affordable options for different budgets. ⏱️ Plan for a journey of approximately 46 hours and 35 minutes, including transfers. 🌟 Get ready for a memorable train ride filled with camaraderie and exploration as you make your way from the Windy City to the heart of the Canadian prairies.
Departure Point
Chicago Union Station
Arrival Point
Winnipeg station
🛫 Traveling from Chicago to Winnipeg by plane offers a convenient and relatively quick journey. With the quickest direct flight taking just 2 hours and 26 minutes, you can reach your destination efficiently. 💸 Depending on the time of booking and airline choice, prices for flights between Chicago and Winnipeg can vary between $206 to $608.
Departure Point
Chicago O'Hare Airport
Arrival Point
Winnipeg Airport

Frequently asked questions

Find out more about the route from Chicago to Winnipeg.

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The cheapest way to travel from Chicago to Winnipeg is by driving. The approximate cost of gas for the round trip is around $190 to $290, depending on the vehicle's fuel efficiency and gas prices. The driving distance is approximately 1,000 miles, which takes about 14 hours and 22 minutes without any stops. However, it is important to consider road conditions, traffic, and other factors that may affect travel time.
The fastest way to travel from Chicago to Winnipeg is by taking a flight. With an estimated flight duration of 7 hours and 59 minutes, you can quickly reach your destination. The cost of a flight ticket can range from $130 to $650, depending on various factors such as the airline, time of booking, and availability. It is advisable to check multiple airlines and compare prices to find the best deal for your travel.
The distance from Chicago to Winnipeg is approximately 721 miles. The road distance is slightly longer at 867.3 miles. This distance can be traveled by driving, taking approximately 14 hours and 22 minutes. Other transportation options, such as flying or taking a train, may offer a shorter travel time but at a higher cost.
The most convenient way to travel from Chicago to Winnipeg without a car is by taking a combination of night bus, bus, and train. You can take a night bus from Chicago to Minneapolis, then transfer to a bus from Minneapolis to Winnipeg. Finally, you can complete the journey by taking a train from Winnipeg to your final destination. This option takes approximately 2 days and can cost between $190 and $360, depending on the specific routes and ticket prices.
The quickest way to travel from Chicago to Winnipeg is by taking a direct flight. Several airlines offer this route and the flight time is typically around 2 hours and 20 minutes. It is recommended to check for deals and compare prices on different airline websites or online travel agencies to find the most affordable option. Additionally, booking in advance and being flexible with travel dates can also help save money on the flight ticket.
There are numerous hotel options available near Winnipeg. With over 192 hotels to choose from, travelers can find accommodation based on their preferences and budget. Prices for hotels in Winnipeg start at $48 per night, offering affordable options for all types of travelers. Whether you prefer luxury hotels or budget-friendly stays, there are plenty of options available in Winnipeg to suit your needs.
Yes, you can drive from Chicago to Winnipeg. The driving distance between the two cities is approximately 867 miles. It takes approximately 14 hours and 22 minutes to drive from Chicago to Winnipeg, depending on traffic and road conditions. It is recommended to plan your stops and rest breaks along the way for a comfortable journey.
To get to Winnipeg from Chicago O'Hare Airport, you can take a connecting flight. Multiple airlines offer flights from the airport to Winnipeg James Armstrong Richardson International Airport. The average flight duration is around 2-3 hours. Once you arrive in Winnipeg, you can take a taxi or use public transportation to reach your desired destination in the city.
There are several airlines that fly between Chicago and Winnipeg. These include WestJet, United Airlines, Delta, and Air Canada. Flights are available from Chicago O'Hare Airport to Winnipeg Airport. It is recommended to check with each airline for the most up-to-date schedules and prices for this route.
The fastest way to travel from Chicago to Winnipeg is by plane. However, there are no direct flights from Chicago O'Hare Airport to Winnipeg Airport. The quickest flight option involves a stopover and takes approximately 5 hours and 9 minutes. Airlines such as WestJet, United Airlines, Delta, and Air Canada offer flights between these two cities. The prices for flights range from $196 to $658. So, flying is the most efficient option for reaching Winnipeg from Chicago, but additional time should be accounted for due to layovers.
The flight duration from Chicago to Winnipeg varies depending on the number of stopovers. However, there is no direct flight between the two cities. The quickest option with one stopover takes around 5 hours and 9 minutes. Keep in mind that flight times may also be affected by factors such as airline schedules and weather conditions.
Trains from Chicago to Winnipeg arrive at the Winnipeg station. This is the main railway station in Winnipeg and serves as the final destination for VIA Rail train services from Chicago. The station is conveniently located in the downtown area, making it easy to access other parts of the city. Upon arrival, travelers can find various amenities including ticket counters, waiting areas, and transportation options to their final destinations within Winnipeg.
No, there is no direct train between Chicago and Winnipeg. However, there are train services available with transfers. The journey begins at Chicago Union Station and includes transfers at Buffalo and Toronto Union Station before arriving in Winnipeg. The total travel time for this route is approximately 2 days and 3 hours.
The Chicago to Winnipeg train departs from Chicago Union Station. This historic and centrally located train station is located at 225 S Canal St, Chicago 60606. It is easily accessible by various transportation options, including public transportation and taxis. It is recommended to arrive at the station at least 30 minutes prior to departure for check-in and boarding procedures.
The cost of a flight from Chicago to Winnipeg can range from $196 to $658. The price may vary depending on factors such as the airline, time of booking, and travel dates. It is recommended to compare different airlines and booking platforms to find the best deals and potentially save money on your flight.
The cost of a train from Chicago to Winnipeg ranges from $188 to $419. The prices may vary depending on factors such as the time of booking and class of service. It is advisable to check and compare different train companies' prices and schedules to find the best deal.
The cost of driving from Chicago to Winnipeg ranges from $190 to $290. This cost includes fuel expenses and tolls. It is important to note that the total cost may vary depending on factors such as the type of vehicle, gas prices, and the route taken.

Trips from Chicago

Trips to Winnipeg