Flight Winnipeg - Chicago, IL prices from $175.76

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$175.76

Winnipeg to Chicago, IL by flight

The journey from Winnipeg to Chicago, IL by flight is 1,156.49 km and takes 12 hrs 40 mins. There are 83 connections per day, with the first departure at 1:00 a.m. and the last at 11:45 p.m.. It is possible to travel from Winnipeg to Chicago, IL by flight for as little as $175.76 or as much as $3,164.08. The best price for this journey is $175.76.

Lowest Price$175.76
Journey Duration12 hrs 40 mins
Connection per Day83
Lowest Price$175.76
Highest Price$3,164.08
First Departure1:00 a.m.
Last Departure11:45 p.m.
Distance1,156.49 km
DepartureWinnipeg
ArrivalChicago, IL
CarriersAir Canada, Viva AerobusMore

Quick and easy travel from Winnipeg to Chicago, IL with Virail

Do you know the best way to get from Winnipeg to Chicago, IL? No? Don't worry, Virail knows. Our search tool uses data from thousands of travel providers to show you all the available routes for your chosen travel dates. Whether you want to travel by train, bus, plane, or carpool, we can help. Filter your results to suit your personal needs: decide whether you want a one-way or round trip ticket, look for a direct journey or one with connections, and choose the time of day that you prefer to travel. Take a look at all the information and find the transport option that's right for you. When you've selected your ideal journey, Virail will transfer you to the website of your chosen travel provider, where you can complete your booking. Your adventure is waiting - let Virail help you today.

How much does it cost to get from Winnipeg to Chicago, IL by plane?

The cheapest plane tickets from Winnipeg to Chicago, IL cost $175.76. On average, you can expect to spend around $722.92 for your plane ticket. Virail will help you find a journey that fits your budget. You can expect prices to vary between different travel providers and methods of transport; often, faster journeys will cost more than slower routes. If your travel dates are flexible, you might be able to find cheaper plane tickets, as prices may fluctuate a little from day to day. You may also find lower prices by booking at certain times of day, avoiding rush hour traffic. Another tip for travelers on a tight budget is to look for connecting journeys. Sometimes it can be cheaper to make a change or two along the way, rather than traveling on a direct route from Winnipeg to Chicago, IL.
Unfortunately, no price was found for your trip from Winnipeg to Chicago, IL. Selecting a new departure or arrival city, without dramatically changing your itinerary could help you find price results.

How long will it take me to travel from Winnipeg to Chicago, IL by plane?

Traveling from Winnipeg to Chicago, IL by plane will usually take 12 hrs 40 mins. This journey covers a distance of 1,156.49 km . When planning your trip, bear in mind that 12 hrs 40 mins is an average, and route times may vary from day to day. Weather conditions, issues with transport, unexpected diversions, and local events could all cause delays to your journey. Please keep the possibility of these exceptional events in mind when making travel plans. In order to get from Winnipeg to Chicago, IL faster, consider looking for an express service that makes fewer stops along the way. Conversely, a connecting route may, in some circumstances, be faster than a direct journey. The fastest routes between Winnipeg and Chicago, IL will complete the journey in 2 hrs 21 mins.On average, it will take you about 12 hrs 40 mins to travel the 1,156.49 km between Winnipeg and Chicago, IL.

Which airports can I use on the Winnipeg to Chicago, IL route?

In Winnipeg, departure airports include Winnipeg Railway Station,Winnipeg James Armstrong Richardson International Airport. When you arrive in Chicago, IL, you may be able to disembark at airports such as Chicago/Rockford International Airport,Chicago Midway International Airport,Union Station,O'Hare International Airport. Remember though that the exact airports served on each route can vary. Different airlines may depart from and arrive at different airports. Furthermore, if you travel on an express service, the number of airports may be limited, and the exact airports served on a particular route may vary at different times of day or day of the week. Check in advance to ensure that you are departing from and arriving at an airport that is convenient for your journey.

How many times a day do departures from Winnipeg leave for Chicago, IL?

The exact number of journeys from Winnipeg to Chicago, IL can vary from day to day. Some services may only run on particular days of the week, while others might be seasonal. In general, an average of 83 departures leave each day. These are run by a number of different transport providers, including . On particularly busy days, there can be up to departures. You can usually expect there to be more connections on weekdays. Many providers run fewer journeys on weekends or public holidays. As a traveler, you may prefer to take a direct route from Winnipeg to Chicago, IL. However, you will find more options available to you if you are willing to take a connecting route. These pass through one or more different cities, and you'll have to change along the way. Not all travelers feel comfortable making multiple connections, but if you are, then you will enjoy greater flexibility when making your booking. The exact number of daily departures from Winnipeg to Chicago, IL varies, but in general, you can expect to find 1 direct connections with no changes leaving each day. Travelers who are happy to take an indirect route will find, on average, 82 journeys with one change or more. Unfortunately, no connection was found for your trip from Winnipeg to Chicago, IL. Selecting a new departure or arrival city, without dramatically changing your itinerary could help you find connections.

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Cheap flight tickets from Winnipeg to Chicago, IL
Looking for the best deal on a train ticket for your trip? Here are 4 ways to get cheap train tickets from Winnipeg to Chicago, IL.

Book in advance and save

If you're looking for the best deal for your trip from Winnipeg to Chicago, IL, booking train tickets in advance is a great way to save money, but keep in mind that advance tickets are usually not available until 3 months before your travel date.

Stay flexible with your travel time and explore off-peak journeys

Planning your trips around off-peak travel times not only means that you'll be able to avoid the crowds, but can also end up saving you money. Being flexible with your schedule and considering alternative routes or times will significantly impact the amount of money you spend on getting from Winnipeg to Chicago, IL.

Always check special offers

Checking on the latest deals can help save a lot of money, making it worth taking the time to browse and compare prices. So make sure you get the best deal on your ticket and take advantage of special fares for children, youth and seniors as well as discounts for groups.

Unlock the potential of slower trains or connecting trains

If you're planning a trip with some flexible time, why not opt for the scenic route? Taking slower trains or connecting trains that make more stops may save you money on your ticket – definitely worth considering if it fits in your schedule.

Best time to book cheap flight tickets from Winnipeg to Chicago, IL

The cheapest Winnipeg - Chicago, IL flight tickets can be found for as low as $290.52 if you’re lucky, or $343.34 on average. The most expensive ticket can cost as much as $433.59.

Find the best day to travel to Chicago, IL by plane

When travelling to Chicago, IL by plane, if you want to avoid crowds you can check how frequently our customers are travelling in the next 30-days using the graph below. On average, the peak hours to travel are between 6:30am and 9am in the morning, or between 4pm and 7pm in the evening. Please keep this in mind when travelling to your point of departure as you may need some extra time to arrive, particularly in big cities!

Carriers on this route

Find out more about the carriers on this route.

Air Canada is the largest airline in Canada, providing scheduled and charter air transportation for passengers and cargo to over 200 destinations worldwide. The airline operates a fleet of over 400 aircraft, including narrow-body and wide-body jets, and serves both domestic and international routes. Air Canada is a member of the Star Alliance, a global airline network that provides passengers with access to over 1,000 destinations in 190 countries. The airline offers a range of services, including in-flight entertainment, Wi-Fi, and a loyalty program called Aeroplan. Air Canada is headquartered in Montreal, Quebec, and has hubs in Toronto, Vancouver, and Calgary.

Alaska Airlines is a major American airline headquartered in Seattle, Washington. It was founded in 1932 and operates a fleet of over 300 aircraft, serving more than 115 destinations across the United States, Canada, Mexico, and Costa Rica. Alaska Airlines is known for its commitment to customer service, on-time performance, and sustainability initiatives. It is a member of the Oneworld airline alliance and has codeshare agreements with several other airlines. Alaska Airlines offers a variety of travel classes, including First Class, Premium Class, and Main Cabin, as well as a loyalty program called Mileage Plan.

Flair Airlines is a Canadian low-cost airline that operates scheduled and charter flights to destinations across Canada, the United States, Mexico, and the Caribbean. Founded in 2005, the airline is headquartered in Edmonton, Alberta, and operates a fleet of Boeing 737 aircraft. Flair Airlines offers a range of fare options, including basic economy, economy, and premium economy, and allows passengers to add on additional services such as baggage, seat selection, and in-flight meals for an additional fee. The airline has grown rapidly in recent years, expanding its route network and increasing its fleet size to meet growing demand for affordable air travel in Canada.

Lynx Air is a regional airline based in Honduras that operates domestic and international flights to destinations in Central America and the Caribbean. The airline was founded in 2006 and has its main hub at Ramón Villeda Morales International Airport in San Pedro Sula. Lynx Air operates a fleet of small aircraft, including Cessna Caravans and Beechcraft 1900s, and offers both scheduled and charter flights. The airline's mission is to provide safe, reliable, and affordable air transportation to its customers, with a focus on serving remote and underserved communities in the region.

Porter Airlines is a regional airline based in Toronto, Canada. It was founded in 2006 and operates flights to various destinations in Canada and the United States. The airline is known for its distinctive brand and high level of customer service, offering amenities such as complimentary snacks and beverages, lounge access, and free Wi-Fi on board. Porter Airlines operates a fleet of Bombardier Q400 turboprop aircraft, which are known for their fuel efficiency and low noise levels. The airline has won numerous awards for its service and has been recognized for its commitment to sustainability and community involvement.

Spirit Airlines is an American ultra-low-cost carrier that operates flights throughout the United States, the Caribbean, Mexico, and Central and South America. The airline was founded in 1983 and is headquartered in Miramar, Florida. Spirit Airlines is known for its low fares and no-frills approach to air travel, with passengers paying extra for amenities such as checked baggage, seat selection, and in-flight refreshments. The airline operates a fleet of Airbus aircraft and has a frequent flyer program called Free Spirit. Despite its low-cost model, Spirit Airlines has faced criticism for its customer service and fees.

United Airlines is a major American airline headquartered in Chicago, Illinois. It is one of the world's largest airlines, operating a comprehensive domestic and international network of flights. United Airlines operates a fleet of over 800 aircraft, serving more than 350 destinations in over 50 countries. The airline is a founding member of the Star Alliance, which is the world's largest airline alliance. United Airlines offers a range of services to its passengers, including in-flight entertainment, Wi-Fi, and a loyalty program called MileagePlus. The airline has a strong commitment to sustainability and has implemented various initiatives to reduce its environmental impact.

Sun Country Airlines is a low-cost American airline headquartered in Minneapolis, Minnesota. It was founded in 1982 and operates scheduled and charter flights to destinations across the United States, Mexico, Central America, and the Caribbean. Sun Country Airline's fleet consists of Boeing 737-800 and 737-700 aircraft, and it offers a variety of services including in-flight entertainment, Wi-Fi, and food and beverage options for purchase. The airline has a reputation for providing affordable fares and friendly service, making it a popular choice for leisure travelers. Sun Country Airlines is committed to safety, sustainability, and customer satisfaction.

Services on board Air Canada, Viva Aerobus and Frontier from Winnipeg to Chicago, IL
Compare services on board when travelling from Winnipeg to Chicago, IL by plane.
Facilities Air Canada Viva Aerobus Frontier Delta Swoop Porter Airlines Lynx Air WestJet Flair Airlines United Airlines Sun Country Airlines Spirit Airlines Alaska Airlines Volaris SWISS
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luggage Luggage check cross cross cross check check cross cross check check cross check cross cross check
food_and_drink Food and drink cross cross check cross check check check check check cross cross check cross cross check

Winnipeg to Chicago, IL CO2 Emissions by Flight

Ecology
Train
80.95kg
Bus
86.74kg
Flight
231.3kg
Car
185.04kg

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Frequently Asked Questions

How much is a flight ticket from Winnipeg to Chicago, IL?
A flight ticket from Winnipeg to Chicago, IL is $722.92. However the price varies depending on how early you buy, and if it's peak time to travel. Occasionally you can find them for as cheap as $175.76.
What's the cheapest flight ticket from Winnipeg to Chicago, IL?
The cheapest ticket you can get from Winnipeg to Chicago, IL is $175.76. We recommend booking as early as possible and off-peak hours to get the cheapest ticket possible. Off-peak times are usually from 09:30 to 16:00, and after 19:00.
What's the distance between Winnipeg and Chicago, IL by flight?
Winnipeg to Chicago, IL is 1,156.49 km.
How long does the flight between Winnipeg and Chicago, IL take?
Winnipeg to Chicago, IL is on average 12 hrs 40 mins. However the fastest option will get you there in 2 hrs 21 mins.
Which companies operate from Winnipeg to Chicago, IL?
The flight journey from Winnipeg to Chicago, IL is covered by 15 operator(s). On Virail you can find these carriers that provide services on this route: Air Canada, Viva Aerobus, Frontier, Delta, _, Swoop, Porter Airlines, Lynx Air, WestJet, Flair Airlines, United Airlines, Sun Country Airlines, Spirit Airlines, Alaska Airlines, Volaris and SWISS.
How many flight connections per day go from Winnipeg to Chicago, IL?
Winnipeg to Chicago, IL has 83 connection(s) per day on average.
What time does the first flight from Winnipeg to Chicago, IL leave?
The earliest flight from Winnipeg to Chicago, IL departs at 1:00 a.m.. However be sure to check with us the schedule on the day you want to leave as the time may differ.
What time does the last flight from Winnipeg to Chicago, IL depart?
The latest flight from Winnipeg to Chicago, IL departs at 11:45 p.m.. However be sure to check with us the schedule on the day you want to leave as the time may differ.
Should I book my ticket from Winnipeg to Chicago, IL in advance?
If you can, we recommend booking your ticket as early as possible to ensure you get better savings. The cheapest flight ticket we have found is $175.76 but this may be subject to change depending on the day of travel, hour you wish to depart and how far in advance you book.
How many direct connections depart from Winnipeg to Chicago, IL?
There are on average 1 direct connection(s) from Winnipeg to go to Chicago, IL.
What's the fastest journey time between Winnipeg to Chicago, IL by flight?
The fastest journey time by flight between Winnipeg and Chicago, IL is 2 hrs 21 mins.
Is there a direct flight from Winnipeg to Chicago, IL?
Yes, there is a direct flight between Winnipeg and Chicago, IL.
What are the CO2 emissions for Winnipeg to Chicago, IL by flight?
The flight journey from Winnipeg to Chicago, IL creates 231.3kg of CO2 emissions.

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