Cheap flights from Winnipeg to Chicago from C$ 309
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 30/11. 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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Fly from
Fly to
Route
Depart
Return
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Fri 15/1
9:35 p.m.-10:50 a.m.
2 stops14h 15m
Chicago O'Hare Intl
Wed 27/1
6:00 a.m.-3:40 p.m.
1 stop8h 40m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Tue 12/1
9:35 p.m.-10:50 a.m.
2 stops14h 15m
Chicago O'Hare Intl
Wed 27/1
6:00 a.m.-3:40 p.m.
1 stop8h 40m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Mon 11/1
9:35 p.m.-10:50 a.m.
2 stops14h 15m
Chicago O'Hare Intl
Wed 27/1
6:00 a.m.-3:40 p.m.
1 stop8h 40m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Thu 22/10
7:00 a.m.-4:40 p.m.
1 stop9h 40m
Chicago O'Hare Intl
Fri 23/10
5:30 p.m.-4:00 p.m.
2 stops22h 30m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Sun 8/11
7:55 p.m.-6:54 a.m.
1 stop11h 59m
Chicago O'Hare Intl
Wed 11/11
7:03 a.m.-3:49 p.m.
1 stop7h 46m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Mon 9/11
6:15 a.m.-2:38 p.m.
1 stop9h 23m
Chicago O'Hare Intl
Fri 13/11
7:03 a.m.-3:49 p.m.
1 stop7h 46m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Wed 21/10
9:05 p.m.-4:40 p.m.
1 stop19h 35m
Chicago O'Hare Intl
Fri 23/10
5:30 p.m.-9:20 a.m.
2 stops15h 50m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Thu 22/10
7:00 a.m.-4:40 p.m.
1 stop9h 40m
Chicago O'Hare Intl
Fri 23/10
5:30 p.m.-8:15 p.m.
1 stop26h 45m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Wed 23/12
2:15 p.m.-4:02 p.m.
Nonstop2h 47m
Chicago O'Hare Intl
Thu 24/12
6:50 a.m.-9:57 p.m.
1 stop14h 07m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Thu 25/2
7:00 a.m.-8:31 a.m.
Nonstop2h 31m
Chicago O'Hare Intl
Sun 28/2
7:15 a.m.-9:55 p.m.
1 stop13h 40m
See travel insights to Chicago from
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 typical price of a round-trip flight between Winnipeg and Chicago?
Prices are currently low for flights on this route.
Typical prices usually range from C$ 676 to C$ 897.The lowest price recently found on this route was C$ 607.
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$ 746.
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$ 846. 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 Monday because tickets tend to average around C$ 1,190. 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 morning is the cheapest time of day to fly from Winnipeg to Chicago when you can find flight prices for as low as C$ 906. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,015 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
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.
Can stopping save me money on Winnipeg to Chicago flights?
You could potentially save up to 22% on your flight if you consider stops on a Winnipeg to Chicago flight.
What is the cheapest airline that flies from Winnipeg to Chicago?
Porter Airlines is the most popular carrier operating from Winnipeg to Chicago
Which airlines fly to Chicago?
United Airlines, Air Canada and WestJet are the top three most popular airlines that fly to Chicago from Winnipeg according to our data. United Airlines is the first choice among our users, with 36% 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 October 2026, 7 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 52% of daily flights taking off in the afternoon.
How many flights depart from Winnipeg to Chicago on average per week?
As of October 2026, there are 51 flights per week flying from Winnipeg to Chicago. The most common day of the week flights depart is Mon, with 16% 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
Frequently asked questions about flying 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 31m 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 October 2026, 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) (84.87% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (6.72%), Boeing 737 MAX 8 (3.36%), and Boeing 737-800 Passenger/BBJ2 (winglets) (1.68%).
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 (45% of total bookings). The next most popular airlines are United Airlines (29%) 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$ 279 | Free Cancellation | Rating 7.2 3,449 reviews | |||
| PriceFrom C$ 707 | Free Cancellation | Rating 7.4 10,288 reviews | |||
| PriceFrom C$ 726 | Free Cancellation | Rating 7.1 11,729 reviews |
United Airlines Flights From Winnipeg to Chicago
United Airlines operates around 12 flights from Winnipeg to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 987, but momondo users have found United Airlines deals from Winnipeg to Chicago from as low as C$ 707 round-trip. United Airlines has been scored 7.4/10 in 10,288 reviews.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.1/10 from 11,729 reviews) operates around 14 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 896, with deals from around C$ 726 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.