Cheap flights from Winnipeg to Chicago from C$ 204
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 17/5. 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 Winnipeg to Chicago
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?
The month of February is another great option to travel to Chicago, with average flight prices from Winnipeg averaging around C$ 608.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as C$ 779. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 922. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.
What is the cheapest time of day to depart on your flight to Chicago?
In the afternoon is the cheapest time of day to fly from Winnipeg to Chicago when you can find flight prices for as low as C$ 719. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 909 per ticket.
What is the cheapest Winnipeg to Chicago flight route?
Fly from Winnipeg to Chicago O'Hare Intl for the best Winnipeg - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Winnipeg when booking 24 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 719 when searching 24 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Winnipeg for as low as C$ 517 on momondo.
What cabin class options are available on Winnipeg to Chicago flights?
There are 4 cabin classes available to choose from on Winnipeg to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Winnipeg to Chicago?
WestJet, Air Canada, and Delta are the most popular carriers operating from Winnipeg to Chicago
Which airlines fly to Chicago?
WestJet, Air Canada and United Airlines are the top three most popular airlines that fly to Chicago from Winnipeg according to our data. WestJet is the first choice among our users, with 40% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Winnipeg to Chicago on average per day?
As of April 2025, 3 flights take off from Winnipeg and land in Chicago each day. The most common flight departure time for this route is 2:00p.m., with 100% of daily flights taking off in the afternoon.
How many flights depart from Winnipeg to Chicago on average per week?
As of April 2025, there are 21 flights per week flying from Winnipeg to Chicago. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.
When to book flights from Winnipeg to Chicago
Cheap Winnipeg to Chicago (YWG to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago
How far is Winnipeg to Chicago by plane?
A flight from Winnipeg to Chicago will travel around 1153.0 km. 2h 21m is a normal flight duration for this route.
When did momondo last update prices for flights from Winnipeg Airport to Chicago?
Prices for flights from Winnipeg Airport to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Winnipeg Airport to Chicago?
As of April 2025, there are 3 operators available to choose from for flights from Winnipeg Airport to Chicago.
How old do you have to be to fly from Winnipeg Airport to Chicago?
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.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago 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. 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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Winnipeg to Chicago is Embraer 175 (Enhanced Winglets) (62.59% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (16.43%), Boeing 737 MAX 8 (7.34%), and Airbus A330-300 (3.15%).
What is the most popular airline from Winnipeg to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Winnipeg to Chicago is Air Canada (47% of total bookings). The next most popular airlines are United Airlines (27%) and WestJet (26%).
Best airlines flying from Winnipeg to Chicago
Compare and see reviews for airlines that fly from Winnipeg to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom C$ 413 | Free Cancellation | Rating 7.2 2,802 reviews | |||
| PriceFrom C$ 476 | Free Cancellation | Rating 7.0 9,083 reviews | |||
| PriceFrom C$ 554 | Free Cancellation | Rating 7.4 8,636 reviews |
United Airlines Flights From Winnipeg to Chicago
United Airlines operates around 7 flights from Winnipeg to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 524, but momondo users have found United Airlines deals from Winnipeg to Chicago from as low as C$ 394 round-trip. United Airlines has been scored 7.4/10 in 8,636 reviews.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.0/10 from 9,085 reviews) operates around 7 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 496, with deals from around C$ 339 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.
Travelling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Winnipeg to Chicago?
Finding the right flight to Chicago from Winnipeg is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Winnipeg to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from Winnipeg which offer a flexible booking policy as well as other useful filters and features.
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.