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, WestJet and Air Canada 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 35% 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 week?

As of September 2026, there are 44 flights per week flying from Winnipeg to Chicago. The most common day of the week flights depart is Mon, with 18% of flights taking off on this day.

How many flights depart from Winnipeg to Chicago on average per day?

As of September 2026, 6 flights take off from Winnipeg and land in Chicago each day. The most common flight departure time for this route is 7:00a.m., with 50% of daily flights taking off at noon.

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 September 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.

C$ 281 Cheap Flights from Winnipeg to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

5:30 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

C$ 415WestJet

Mon, 19 Oct - Thu, 22 Oct

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

5:30 p.m. - 9:35 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

16h 05m2 stops Calgary Saskatoon

C$ 466WestJet

Mon, 19 Oct - Fri, 23 Oct

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

5:30 p.m. - 9:35 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

16h 05m2 stops Calgary Saskatoon

C$ 467WestJet

Mon, 19 Oct - Thu, 22 Oct

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

6:20 p.m. - 9:15 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

C$ 495Multiple Airlines

Thu, 22 Oct - Mon, 26 Oct

5:00 a.m. - 5:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

12h 40m1 stop Toronto Pearson Intl

6:20 p.m. - 9:15 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

C$ 515Multiple Airlines

Tue, 27 Oct - Wed, 28 Oct

5:10 p.m. - 11:40 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

18h 30m1 stop Toronto Pearson Intl

12:20 p.m. - 12:44 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

12h 24m1 stop Toronto Island

C$ 522Multiple Airlines

Sat, 24 Oct - Mon, 26 Oct

7:15 a.m. - 3:38 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

8h 23m1 stop Toronto Pearson Intl

4:30 p.m. - 11:44 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 14m1 stop Toronto Pearson Intl

C$ 710Air Canada

Mon, 7 Dec - Tue, 8 Dec

5:00 a.m. - 1:23 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

8h 23m1 stop Toronto Pearson Intl

9:55 a.m. - 6:12 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 17m1 stop Toronto Pearson Intl

C$ 726Air Canada

Wed, 14 Oct - Wed, 21 Oct

11:05 a.m. - 9:15 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

22h 10m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

6:20 p.m. - 11:49 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

17h 29m2 stops Boston Logan Intl Toronto Pearson Intl

C$ 926United Airlines

Mon, 7 Dec - Tue, 8 Dec

2:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 949United Airlines

Thu, 12 Nov - Tue, 17 Nov

Cheap last-minute flights

Enter your travel dates to find the best prices.

7:20 a.m. - 5:05 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 45m1 stop Calgary

9:55 a.m. - 6:12 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 17m1 stop Toronto Pearson Intl

C$ 1,061Air Canada

Wed, 23 Sep - Wed, 30 Sep

5:44 p.m. - 9:33 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

3h 49m1 stop Minneapolis St Paul

5:30 p.m. - 8:20 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

26h 50m1 stop Calgary

C$ 1,089Multiple Airlines

Fri, 25 Sep - Sun, 27 Sep

6:15 a.m. - 9:49 a.m.YWG Winnipeg-MDW Chicago Midway

27h 34m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

9:29 a.m. - 12:55 a.m.MDW Chicago Midway-YWG Winnipeg

15h 26m2 stops Detroit Metropolitan Wayne County Calgary

C$ 1,124WestJet

Wed, 23 Sep - Wed, 30 Sep

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:55 a.m. - 6:12 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 17m1 stop Toronto Pearson Intl

C$ 1,124Air Canada

Wed, 23 Sep - Wed, 30 Sep

7:45 a.m. - 9:49 a.m.YWG Winnipeg-MDW Chicago Midway

26h 04m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

9:59 a.m. - 4:54 p.m.MDW Chicago Midway-YWG Winnipeg

6h 55m1 stop Minneapolis St Paul

C$ 1,127WestJet

Wed, 23 Sep - Wed, 30 Sep

9:05 p.m. - 11:51 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

14h 46m2 stops Calgary Atlanta Hartsfield-Jackson

5:30 p.m. - 8:20 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

26h 50m1 stop Calgary

C$ 1,162Multiple Airlines

Fri, 25 Sep - Sun, 27 Sep

5:10 p.m. - 11:00 a.m.YWG Winnipeg-MDW Chicago Midway

17h 50m1 stop Toronto Pearson Intl

3:20 p.m. - 8:40 a.m.MDW Chicago Midway-YWG Winnipeg

17h 20m1 stop Toronto Island

C$ 1,169Multiple Airlines

Thu, 24 Sep - Wed, 30 Sep

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

6:00 a.m. - 8:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

14h 57m1 stop Denver Intl

C$ 1,296United Airlines

Fri, 25 Sep - Sun, 27 Sep

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

10:00 a.m. - 12:37 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

C$ 1,307Air Canada

Wed, 23 Sep - Wed, 30 Sep

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

5:00 a.m. - 8:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

15h 57m1 stop Denver Intl

C$ 1,384United Airlines

Thu, 24 Sep - Wed, 30 Sep

Cheap direct flights

Enter your travel dates to find the best prices.

2:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 949United Airlines

Thu, 12 Nov - Tue, 17 Nov

2:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:29 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 54mdirect

C$ 949United Airlines

Tue, 27 Oct - Wed, 28 Oct

2:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 949United Airlines

Wed, 18 Nov - Sun, 22 Nov

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:29 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 54mdirect

C$ 952United Airlines

Thu, 22 Oct - Mon, 26 Oct

2:15 p.m. - 5:00 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mdirect

9:35 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,068Air Canada

Fri, 11 Dec - Sun, 13 Dec

2:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,071Air Canada

Tue, 3 Nov - Tue, 10 Nov

2:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,103Multiple Airlines

Thu, 29 Oct - Sun, 1 Nov

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

7:54 p.m. - 10:33 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mdirect

C$ 1,134Air Canada

Fri, 9 Oct - Sun, 11 Oct

2:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,207Multiple Airlines

Sat, 14 Nov - Mon, 16 Nov

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

10:00 a.m. - 12:37 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

C$ 1,534Multiple Airlines

Sun, 18 Oct - Sat, 24 Oct

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

WestJet

19 Oct

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

ORD4:40 p.m.Chicago O'Hare Intl

22 Oct

ORD5:30 p.m.Chicago O'Hare Intl

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 415

WestJet

19 Oct

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

ORD4:40 p.m.Chicago O'Hare Intl

23 Oct

ORD5:30 p.m.Chicago O'Hare Intl

16h 05m

2 stops

YWG9:35 a.m.Winnipeg

C$ 466

WestJet

19 Oct

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

ORD4:40 p.m.Chicago O'Hare Intl

22 Oct

ORD5:30 p.m.Chicago O'Hare Intl

16h 05m

2 stops

YWG9:35 a.m.Winnipeg

C$ 467

American Airlines flights from Winnipeg to Chicago

Our best American Airlines deals on Winnipeg to Chicago flight tickets

American Airlines

3 Nov

YWG7:00 a.m.Winnipeg

7h 37m

1 stop

ORD2:37 p.m.Chicago O'Hare Intl

10 Nov

ORD2:50 p.m.Chicago O'Hare Intl

7h 07m

1 stop

YWG9:57 p.m.Winnipeg

C$ 600

American Airlines

31 Oct

YWG7:00 a.m.Winnipeg

7h 20m

1 stop

ORD2:20 p.m.Chicago O'Hare Intl

6 Nov

ORD2:50 p.m.Chicago O'Hare Intl

7h 07m

1 stop

YWG9:57 p.m.Winnipeg

C$ 605

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 19/10

7:00 a.m.-4:40 p.m.

1 stop9h 40m

Chicago O'Hare Intl

Thu 22/10

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 415

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 19/10

7:00 a.m.-4:40 p.m.

1 stop9h 40m

Chicago O'Hare Intl

Fri 23/10

5:30 p.m.-9:35 a.m.

2 stops16h 05m

C$ 466

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 19/10

7:00 a.m.-4:40 p.m.

1 stop9h 40m

Chicago O'Hare Intl

Thu 22/10

5:30 p.m.-9:35 a.m.

2 stops16h 05m

C$ 467

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

Mon 26/10

6:20 p.m.-9:15 a.m.

1 stop14h 55m

C$ 495

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 27/10

5:00 a.m.-5:40 p.m.

1 stop12h 40m

Chicago O'Hare Intl

Wed 28/10

6:20 p.m.-9:15 a.m.

1 stop14h 55m

C$ 515

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 24/10

5:10 p.m.-11:40 a.m.

1 stop18h 30m

Chicago O'Hare Intl

Mon 26/10

12:20 p.m.-12:44 a.m.

1 stop12h 24m

C$ 522

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 7/12

7:15 a.m.-3:38 p.m.

1 stop8h 23m

Chicago O'Hare Intl

Tue 8/12

4:30 p.m.-11:44 p.m.

1 stop7h 14m

C$ 710

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 14/10

5:00 a.m.-1:23 p.m.

1 stop8h 23m

Chicago O'Hare Intl

Wed 21/10

9:55 a.m.-6:12 p.m.

1 stop8h 17m

C$ 726

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 7/12

11:05 a.m.-9:15 a.m.

2 stops22h 10m

Chicago O'Hare Intl

Tue 8/12

6:20 p.m.-11:49 a.m.

2 stops17h 29m

C$ 926

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 12/11

2:15 p.m.-4:50 p.m.

Nonstop2h 35m

Chicago O'Hare Intl

Tue 17/11

9:35 a.m.-12:23 p.m.

Nonstop2h 48m

C$ 949

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

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$ 553 to C$ 917.
The lowest price recently found on this route was C$ 415.

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$ 731.

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$ 858. 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$ 1,158. 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$ 892. 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$ 993 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 38% on your flight if you consider stops on a Winnipeg to Chicago flight.

How have Winnipeg to Chicago flight prices changed over time?

As of September 2026, prices for Winnipeg to Chicago flights are approximately 9% cheaper when compared to flights at the same time last year.

When to book flights from Winnipeg to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Winnipeg to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

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

Best price found	C$ 281
Fastest flight time	2h 31m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Winnipeg in the past 72 hours is C$ 281. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 415.

The fastest flight from Winnipeg to Chicago takes 2h 31m

Direct flights go from Winnipeg to Chicago every day.

There are 3 airports in Chicago. From Winnipeg there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

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 September 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) (85.37% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (6.50%), Boeing 737 MAX 8 (3.25%), and Boeing 737-800 Passenger/BBJ2 (winglets) (1.63%).
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 (44% of total bookings). The next most popular airlines are United Airlines (30%) 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
WestJet	PriceFrom C$ 274	Free Cancellation	Rating 7.2 3,446 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 694	Free Cancellation	Rating 7.4 10,222 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 712	Free Cancellation	Rating 7.1 11,658 reviews	Search Air Canada flights

United Airlines Flights From Winnipeg to Chicago
United Airlines operates around 10 flights from Winnipeg to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 968, but momondo users have found United Airlines deals from Winnipeg to Chicago from as low as C$ 694 round-trip. United Airlines has been scored 7.4/10 in 10,222 reviews.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.1/10 from 11,658 reviews) operates around 12 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 879, with deals from around C$ 712 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.

Merrillville

Benton Harbor

Hammond

Munster

Valparaiso

Portage

Why 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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Wed 21/10

Wed 28/10

Email me momondo's favourite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Airlines

Cabin classes

Other United States destinations

Other flights from Winnipeg

Complete your trip

Feeling lucky

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Cheap flights from Winnipeg to Chicago from C$ 281

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 2/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last-minute flights

Cheap direct flights

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

American Airlines flights from Winnipeg to Chicago

Our best American Airlines deals on Winnipeg to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Winnipeg to Chicago

What is the typical price of a round-trip flight between Winnipeg and Chicago?

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Winnipeg to Chicago flight route?

What cabin class options are available on Winnipeg to Chicago flights?

Can stopping save me money on Winnipeg to Chicago flights?

How have Winnipeg to Chicago flight prices changed over time?

What is the cheapest airline that flies from Winnipeg to Chicago?

Which airlines fly to Chicago?

How many flights depart from Winnipeg to Chicago on average per day?

How many flights depart from Winnipeg to Chicago on average per week?

When to book flights from Winnipeg to Chicago

Cheap Winnipeg to Chicago (YWG to CHI) flight deals and tips

Best price found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Winnipeg to Chicago

Best airlines flying from Winnipeg to Chicago

Compare and see reviews for airlines that fly from Winnipeg to Chicago with momondo

Travelling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago

Fly your favourite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular Cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from Winnipeg

According to popular flight searches on momondo this year

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year