Cheap flights from Winnipeg to Chicago from $177
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 8/4. 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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WestJet flights from Winnipeg to Chicago O'Hare Intl Airport
Our best WestJet deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
Air Canada flights from Winnipeg to Chicago O'Hare Intl Airport
Our best Air Canada 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 cheapest month to fly to Chicago O'Hare Intl Airport?
The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around $403.
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 $411. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Winnipeg because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $877.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from Winnipeg at noon is the least expensive time of day to depart. momondo users have found prices as low as $628 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $641. Of course, these prices can vary depending on the time of year and what airport you fly to.
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 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $462 when searching 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 $276 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 68% more expensive when compared to flights at the same time last year.
How many flights depart from Winnipeg to Chicago O'Hare Intl Airport on average per day?
As of June 2025, 7 flights take off from Winnipeg and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 7:00AM, with 61% of daily flights taking off at noon.
How many flights depart from Winnipeg to Chicago O'Hare Intl Airport on average per week?
As of June 2025, there are 55 flights per week flying from Winnipeg to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Mon, with 15% of flights 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?
There are 702.3 mi between Winnipeg and Chicago O'Hare Intl. A reasonable flight in good conditions will take 2h 31m.
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 refresh daily.
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 2 as of June 2025.
How old do you have to be to fly from Winnipeg Airport to Chicago O'Hare Intl Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Winnipeg to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Winnipeg and Chicago O'Hare Intl Airport, the leading plane model is Embraer 175 (Enhanced Winglets), making up 72.43% of the total bookings. Other popular models include Boeing 737-700 Passenger/BBJ1 (winglets) with 8.09%, Boeing 737 MAX 8 with 5.51%, and Airbus A330-300 with 3.31%.
What is the most popular airline from Winnipeg to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Winnipeg and Chicago O'Hare Intl Airport, the leading airline is United Airlines, making up 52% of the total bookings. Other popular airlines include Air Canada with 48%.
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 $222 | Free Cancellation | Rating 7.1 9,657 reviews | |||
| PriceFrom $443 | Free Cancellation | Rating 7.4 8,852 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 8,852 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 $443 (round-trip), much lower than the average airfare cost of $729 for United Airlines flights on this route.
Air Canada Flights From Winnipeg to Chicago O'Hare Intl Airport
Another popular option for Winnipeg to Chicago O'Hare Intl Airport flights is Air Canada (7.1/10, 9,654 ratings). Air Canada flies from Winnipeg to Chicago O'Hare Intl Airport around 14 times per week, with deals starting from $222 round-trip and rising to an average price of around $550.
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Why should I use momondo to find a flight deal from Winnipeg to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Winnipeg.
Can I find flights from Winnipeg to Chicago with flexible booking policies on momondo?
Flights from Winnipeg to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Winnipeg to Chicago?
Once all potential Winnipeg to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Winnipeg to Chicago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Winnipeg and alert you when they change.