Cheap flights from Winnipeg to Chicago from C$ 208
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Chicago departing on 1/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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United Airlines flights from Winnipeg to Chicago O'Hare Intl Airport
Our best United Airlines deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
Delta flights from Winnipeg to Chicago O'Hare Intl Airport
Our best Delta deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
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How to get the cheapest flight ticket from Winnipeg to Chicago O'Hare Intl Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Winnipeg and Chicago O'Hare Intl Airport?
What is the cheapest month to fly to Chicago O'Hare Intl Airport?
In general, May is the cheapest month to fly from Winnipeg to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 551. The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around C$ 565.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as C$ 756. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Chicago O'Hare Intl Airport for around C$ 934.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
In the evening is the cheapest time of day to fly from Winnipeg to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 695. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are C$ 949 on average. Flights to Chicago O'Hare Intl Airport from Winnipeg in the afternoon are generally more expensive because this time of day is more convenient for travellers’ schedules.
What is the cheapest Winnipeg to Chicago O'Hare Intl flight route?
Fly from Winnipeg to Chicago O'Hare Intl for the best Winnipeg - Chicago O'Hare Intl flight prices
How far in advance should I book a flight to Chicago O'Hare Intl Airport?
You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Winnipeg when booking 24 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around C$ 645 when searching 24 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Winnipeg for as low as C$ 377 on momondo.
What cabin class options are available on Winnipeg to Chicago O'Hare Intl flights?
There are 4 cabin classes available to choose from on Winnipeg to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Winnipeg to Chicago O'Hare Intl Airport flights?
You could potentially save up to 55% on your flight if you consider stops on a Winnipeg to Chicago O'Hare Intl Airport flight.
How have Winnipeg to Chicago O'Hare Intl Airport flight prices changed over time?
As of June 2025, prices for Winnipeg to Chicago O'Hare Intl Airport flights are approximately 60% more expensive when compared to flights at the same time last year.
What is the cheapest airline that flies from Winnipeg to Chicago O'Hare Intl?
WestJet, United Airlines, and Delta are the most popular carriers operating from Winnipeg to Chicago O'Hare Intl
Which airlines fly to Chicago O'Hare Intl Airport?
United Airlines, Air Canada and WestJet are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Winnipeg according to our data. United Airlines is the first choice among our users, with 43% of people opting to fly with this airline when travelling to Chicago O'Hare Intl Airport. Keep in mind that there are 3 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Winnipeg to Chicago O'Hare Intl Airport on average per day?
7 flights are operational daily from Winnipeg to Chicago O'Hare Intl Airport as of June 2025. The most popular departure time for this route is 7:00a.m., with 61% of flights per day taking off at noon.
How many flights depart from Winnipeg to Chicago O'Hare Intl Airport on average per week?
54 flights are operational weekly from Winnipeg to Chicago O'Hare Intl Airport as of June 2025. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.
When to book flights from Winnipeg to Chicago O'Hare Intl Airport
Cheap Winnipeg to Chicago O'Hare Intl Airport (YWG to ORD) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago O'Hare Intl Airport
How far is Winnipeg to Chicago O'Hare Intl by plane?
Winnipeg and Chicago O'Hare Intl are 1130.2 km apart from one another. Flights usually cover this in 2h 31m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Winnipeg Airport to Chicago O'Hare Intl Airport?
Prices for flights from Winnipeg Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Winnipeg Airport to Chicago O'Hare Intl Airport?
The number of operators available for flights from Winnipeg Airport to Chicago O'Hare Intl Airport is 3 as of June 2025.
How old do you have to be to fly from Winnipeg Airport to Chicago O'Hare Intl Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Winnipeg to Chicago O'Hare Intl Airport?
momondo data reveals that the most frequently booked plane model on the route from Winnipeg to Chicago O'Hare Intl Airport is Embraer 175 (Enhanced Winglets), representing 74.61% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 5.86%, Boeing 737-700 Passenger/BBJ1 (winglets) at 3.91%, and Airbus A330-300 at 3.52%.
What is the most popular airline from Winnipeg to Chicago O'Hare Intl Airport?
momondo data reveals that the most frequently booked airline on the route from Winnipeg to Chicago O'Hare Intl Airport is United Airlines, representing 43% of all bookings. The subsequent popular airlines are Air Canada at 41% and WestJet at 16%.
Best airlines flying from Winnipeg to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Winnipeg to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom C$ 198 | Free Cancellation | Rating 7.2 2,868 reviews | |||
| PriceFrom C$ 375 | Free Cancellation | Rating 7.1 9,537 reviews | |||
| PriceFrom C$ 539 | Free Cancellation | Rating 7.4 8,790 reviews |
United Airlines Flights From Winnipeg to Chicago O'Hare Intl Airport
United Airlines flies from Winnipeg to Chicago O'Hare Intl Airport around 14 times per week, with 8,790 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Winnipeg to Chicago O'Hare Intl Airport in the last 72 hours was C$ 394 (round-trip), much lower than the average airfare cost of C$ 497 for United Airlines flights on this route.
Air Canada Flights From Winnipeg to Chicago O'Hare Intl Airport
Air Canada is also a popular choice for this route. Air Canada flight deals for Winnipeg to Chicago O'Hare Intl Airport start from as low as C$ 274 round-trip, depending on your selected dates, with average Air Canada deals seen on momondo around C$ 470. Air Canada operates 14 flights to Chicago O'Hare Intl Airport from Winnipeg in an average week. Users have rated it 7.1/10 across 9,531 reviews.
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Why should I use momondo to find a flight deal from Winnipeg to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Winnipeg to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Winnipeg to Chicago with flexible booking policies on momondo?
All flight searches from Winnipeg to Chicago on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Winnipeg to Chicago?
Once you have performed a search for Winnipeg to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Winnipeg to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Winnipeg. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.