Cheap flights from Chicago to Winnipeg from $111
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Winnipeg departing on 7/8. 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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How to get the cheapest flight ticket from Chicago to Winnipeg
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 Winnipeg?
In general, May is the cheapest month to fly from Chicago to Winnipeg. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $271. If you’re not able to fly to Winnipeg in May, then January is your next best option. Flight prices from Chicago to Winnipeg during January average around $319.
What is the cheapest day to depart on your flight to Winnipeg?
The cheapest day to depart on your flight to Winnipeg is on a Friday when prices can be found for as low as $563. This is often the case because there is less demand to fly during this day of the week. On the other hand, Tuesday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $638.
What is the cheapest time of day to depart on your flight to Winnipeg?
The cheapest time of day to fly to Winnipeg is in the evening when flights can be purchased for as low as $562. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $619 on average. Flights to Winnipeg from Chicago at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.
What is the cheapest Chicago to Winnipeg flight route?
Fly from Chicago O'Hare Intl to Winnipeg for the best Chicago - Winnipeg flight prices
What cabin class options are available on Chicago to Winnipeg flights?
There are 3 cabin classes available to choose from on Chicago to Winnipeg 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 Chicago to Winnipeg flights?
You could potentially save up to 10% on your flight if you consider stops on a Chicago to Winnipeg flight.
How many flights depart from Chicago to Winnipeg on average per day?
The number of flights available between Chicago and Winnipeg is 6 per day as of June 2025. The most frequent departure time is 7:00PM, with 51% of daily flights leaving in the afternoon.
How many flights depart from Chicago to Winnipeg on average per week?
45 flights are operational weekly from Chicago to Winnipeg as of June 2025. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.
When to book flights from Chicago to Winnipeg
Cheap Chicago to Winnipeg (CHI to YWG) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Winnipeg
How far is Chicago to Winnipeg by plane?
A flight from Chicago to Winnipeg will travel around 716.4 mi. Flights usually cover this in 2h 35m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago to Winnipeg Airport?
Prices for flights from Chicago to Winnipeg Airport refresh daily.
How many operators does momondo search for flights from Chicago to Winnipeg Airport?
As of June 2025, there are 2 operators available to choose from for flights from Chicago to Winnipeg Airport.
How old do you have to be to fly from Chicago to Winnipeg Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Winnipeg Airport.
What documentation or ID do you need to fly to Winnipeg Airport?
The travel and health documents required for your trip to Winnipeg 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 Winnipeg 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 Chicago to Winnipeg?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Winnipeg is Embraer 175 (Enhanced Winglets) (83.65% of total bookings). The next most popular plane models are Boeing 777-300ER (4.81%), Boeing 737-800 (1.92%), and Airbus A350-1000 (1.92%).
What is the most popular airline from Chicago to Winnipeg?
momondo data reveals that the most frequently booked airline on the route from Chicago to Winnipeg is United Airlines, representing 57% of all bookings. The subsequent popular airline is Air Canada at 43%.
Best airlines flying from Chicago to Winnipeg
Compare and see reviews for airlines that fly from Chicago to Winnipeg with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $230 | Free Cancellation | Rating 7.1 9,531 reviews | |||
| PriceFrom $354 | Free Cancellation | Rating 7.4 8,790 reviews |
United Airlines Flights From Chicago to Winnipeg
United Airlines flies from Chicago to Winnipeg around 13 times per week, with 8,790 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Chicago to Winnipeg in the last 72 hours was $354 (round-trip), much lower than the average airfare cost of $641 for United Airlines flights on this route.
Air Canada Flights From Chicago to Winnipeg
The best Air Canada deal for Chicago to Winnipeg flight tickets found on momondo in the last 72 hours was $230, round-trip. It should be noted that an average Air Canada flight deal for this route in this time was higher, at $601 round-trip. Air Canada operates 13 flights out of Chicago into Winnipeg in an average week, so prices vary by time and availability. 9,537 Air Canada reviews by users on momondo have scored the airline at 7.1/10.
Traveling to a place near Winnipeg?
Book flights to Winnipeg if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Winnipeg?
Finding the right flight to Winnipeg from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Winnipeg quick and easy, saving you time and money.
Can I find flights from Chicago to Winnipeg with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Winnipeg from Chicago with this policy.
How can momondo help me find flights from Chicago to Winnipeg?
Once you have performed a search for Chicago to Winnipeg 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 Chicago to Winnipeg right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Chicago to Winnipeg now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Winnipeg and let you know when they change.