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

As of October 2026, 2 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.

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

Porter Airlines and WestJet are the most popular carriers 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 week?

As of October 2026, there are 14 flights per week flying from Winnipeg to Chicago. The most common day of the week flights depart is Wed, with 29% of flights taking off on this day.

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.

C$ 296 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.

7:55 p.m. - 11:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

16h 40m1 stop Toronto Pearson Intl

6:20 p.m. - 10:15 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

C$ 555Multiple Airlines

Mon, 14 Dec - Wed, 16 Dec

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

25h 00m2 stops Ottawa Toronto Island

6:20 p.m. - 10:15 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

C$ 566Multiple Airlines

Tue, 5 Jan - Thu, 7 Jan

7:00 a.m. - 11:50 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

29h 50m1 stop Atlanta Hartsfield-Jackson

6:20 p.m. - 10:15 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

C$ 566Multiple Airlines

Mon, 1 Feb - Thu, 4 Feb

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$ 649WestJet

Mon, 26 Apr - Mon, 3 May

3:45 p.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

24h 55m1 stop Calgary

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

7h 25m1 stop Calgary

C$ 743WestJet

Sat, 24 Apr - Sun, 2 May

8:15 a.m. - 1:13 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

5h 58m1 stop Toronto Pearson Intl

8:50 p.m. - 11:09 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

13h 19m1 stop Toronto Pearson Intl

C$ 835Air Canada

Tue, 26 Jan - Fri, 29 Jan

9:05 a.m. - 2:52 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

6h 47m1 stop Montreal Pierre Elliott Trudeau Intl

4:30 p.m. - 1:24 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 54m1 stop Toronto Pearson Intl

C$ 934Air Canada

Thu, 25 Feb - Sun, 28 Feb

1:10 p.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

27h 30m2 stops Edmonton Calgary

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

7h 25m1 stop Calgary

C$ 937WestJet

Sat, 24 Apr - Sun, 2 May

8:00 a.m. - 9:31 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 31mdirect

3:35 p.m. - 7:26 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 51mdirect

C$ 1,105United Airlines

Thu, 25 Feb - Sun, 28 Feb

3:15 p.m. - 5:02 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 47mdirect

10:00 a.m. - 1:52 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 52mdirect

C$ 1,105United Airlines

Sat, 26 Dec - Sun, 27 Dec

Cheap last-minute flights

Enter your travel dates to find the best prices.

6:00 a.m. - 5:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

12h 40m1 stop Toronto Pearson Intl

6:20 p.m. - 7:14 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

23h 54m2 stops Toronto Island Ottawa

C$ 957Multiple Airlines

Tue, 3 Nov - Mon, 30 Nov

6:00 a.m. - 5:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

12h 40m1 stop Toronto Pearson Intl

6:20 p.m. - 12:05 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

16h 45m1 stop Toronto Island

C$ 976Multiple Airlines

Tue, 3 Nov - Mon, 30 Nov

9:05 p.m. - 11:34 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

15h 29m1 stop Toronto Pearson Intl

6:20 p.m. - 7:14 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

23h 54m2 stops Toronto Island Ottawa

C$ 1,001Multiple Airlines

Wed, 4 Nov - Mon, 30 Nov

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,217Air Canada

Tue, 3 Nov - Thu, 5 Nov

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

2:30 p.m. - 9:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

6h 27m1 stop Denver Intl

C$ 1,231Air Canada

Tue, 3 Nov - Thu, 5 Nov

6:15 a.m. - 1:13 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

7h 58m1 stop Toronto Pearson Intl

2:30 p.m. - 9:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

6h 27m1 stop Denver Intl

C$ 1,249Air Canada

Tue, 3 Nov - Thu, 5 Nov

6:00 a.m. - 8:30 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

15h 30m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

6:20 a.m. - 12:19 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

16h 59m1 stop Minneapolis St Paul

C$ 1,403WestJet

Tue, 3 Nov - Thu, 5 Nov

8:35 a.m. - 10:05 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

14h 30m2 stops Calgary Salt Lake City

7:00 a.m. - 8:50 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

12h 50m2 stops New York LaGuardia Toronto Pearson Intl

C$ 1,431WestJet

Tue, 3 Nov - Thu, 5 Nov

6:15 a.m. - 11:57 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

6h 42m1 stop Toronto Pearson Intl

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,450United Airlines

Tue, 3 Nov - Mon, 30 Nov

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 2,172United Airlines

Tue, 3 Nov - Thu, 5 Nov

Cheap direct flights

Enter your travel dates to find the best prices.

3:15 p.m. - 5:00 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,001Air Canada

Mon, 14 Dec - Wed, 16 Dec

8:00 a.m. - 9:31 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 31mdirect

3:35 p.m. - 7:26 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 51mdirect

C$ 1,003Air Canada

Thu, 25 Feb - Sun, 28 Feb

8:00 a.m. - 9:45 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mdirect

3:50 p.m. - 7:28 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 38mdirect

C$ 1,010Air Canada

Tue, 5 Jan - Thu, 7 Jan

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,052Air Canada

Thu, 12 Nov - Tue, 17 Nov

8:00 a.m. - 9:31 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 31mdirect

3:35 p.m. - 7:26 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 51mdirect

C$ 1,105United Airlines

Thu, 25 Feb - Sun, 28 Feb

3:15 p.m. - 5:02 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 47mdirect

10:00 a.m. - 1:52 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 52mdirect

C$ 1,105United Airlines

Sat, 26 Dec - Sun, 27 Dec

8:00 a.m. - 9:45 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mdirect

3:50 p.m. - 7:28 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 38mdirect

C$ 1,105United Airlines

Sun, 7 Feb - Wed, 10 Feb

8:00 a.m. - 9:45 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mdirect

3:50 p.m. - 7:28 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 38mdirect

C$ 1,234Multiple Airlines

Tue, 26 Jan - Fri, 29 Jan

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,262Multiple Airlines

Mon, 23 Nov - Fri, 27 Nov

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,291Multiple Airlines

Mon, 23 Nov - Fri, 27 Nov

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American Airlines flights from Winnipeg to Chicago

Our best American Airlines deals on Winnipeg to Chicago flight tickets

American Airlines

26 Nov

YWG7:00 a.m.Winnipeg

8h 36m

1 stop

ORD2:36 p.m.Chicago O'Hare Intl

3 Dec

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

7h 07m

1 stop

YWG10:57 p.m.Winnipeg

C$ 758

American Airlines

12 Nov

YWG7:00 a.m.Winnipeg

7h 01m

1 stop

ORD1:01 p.m.Chicago O'Hare Intl

17 Nov

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

7h 02m

1 stop

YWG10:52 p.m.Winnipeg

C$ 759

American Airlines

23 Nov

YWG7:00 a.m.Winnipeg

7h 10m

1 stop

ORD1:10 p.m.Chicago O'Hare Intl

27 Nov

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

7h 02m

1 stop

YWG10:52 p.m.Winnipeg

C$ 765

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

WestJet

24 Apr

YWG3:45 p.m.Winnipeg

24h 55m

1 stop

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

2 May

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 743

WestJet

5 Dec

YWG9:35 p.m.Winnipeg

13h 53m

2 stops

MDW10:28 a.m.Chicago Midway

8 Dec

MDW10:24 a.m.Chicago Midway

24h 07m

1 stop

YWG11:31 a.m.Winnipeg

C$ 1,094

WestJet

21 Nov

YWG12:44 p.m.Winnipeg

24h 06m

1 stop

MDW11:50 a.m.Chicago Midway

24 Nov

MDW10:34 a.m.Chicago Midway

24h 20m

1 stop

YWG11:54 a.m.Winnipeg

C$ 1,098

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 14/12

7:55 p.m.-11:35 a.m.

1 stop16h 40m

Chicago O'Hare Intl

Wed 16/12

6:20 p.m.-10:15 a.m.

1 stop14h 55m

C$ 555

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 5/1

11:40 a.m.-11:40 a.m.

2 stops25h 00m

Chicago O'Hare Intl

Thu 7/1

6:20 p.m.-10:15 a.m.

1 stop14h 55m

C$ 566

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 1/2

7:00 a.m.-11:50 a.m.

1 stop29h 50m

Chicago O'Hare Intl

Thu 4/2

6:20 p.m.-10:15 a.m.

1 stop14h 55m

C$ 566

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 26/4

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 3/5

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

1 stop7h 25m

C$ 649

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 24/4

3:45 p.m.-4:40 p.m.

1 stop24h 55m

Chicago O'Hare Intl

Sun 2/5

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

1 stop7h 25m

C$ 743

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 26/1

8:15 a.m.-1:13 p.m.

1 stop5h 58m

Chicago O'Hare Intl

Fri 29/1

8:50 p.m.-11:09 a.m.

1 stop13h 19m

C$ 835

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 25/2

9:05 a.m.-2:52 p.m.

1 stop6h 47m

Chicago O'Hare Intl

Sun 28/2

4:30 p.m.-1:24 a.m.

1 stop7h 54m

C$ 934

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 24/4

1:10 p.m.-4:40 p.m.

2 stops27h 30m

Chicago O'Hare Intl

Sun 2/5

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

1 stop7h 25m

C$ 937

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 25/2

8:00 a.m.-9:31 a.m.

Nonstop2h 31m

Chicago O'Hare Intl

Sun 28/2

3:35 p.m.-7:26 p.m.

Nonstop2h 51m

C$ 1,105

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 26/12

3:15 p.m.-5:02 p.m.

Nonstop2h 47m

Chicago O'Hare Intl

Sun 27/12

10:00 a.m.-1:52 p.m.

Nonstop2h 52m

C$ 1,105

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 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 Saturday when prices can be found for as low as C$ 905. 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$ 1,177. 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$ 910. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,284 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 31% 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 October 2026, prices for Winnipeg to Chicago flights are approximately 24% more expensive 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$ 296
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$ 296. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 555.

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).

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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) (84.67% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (8.76%), Boeing 737-800 Passenger/BBJ2 (winglets) (2.19%), and Boeing 737-700 Passenger/BBJ1 (winglets) (1.46%).
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 (29%) and WestJet (24%).

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 3,442 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 694	Free Cancellation	Rating 7.3 10,453 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 712	Free Cancellation	Rating 7.1 11,833 reviews	Search Air Canada flights

United Airlines Flights From Winnipeg to Chicago
United Airlines operates around 3 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 7.3/10 in 10,453 reviews.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.1/10 from 11,833 reviews) operates around 4 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 889, 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

Hammond

Benton Harbor

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.

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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$ 296

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 11/12. 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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Cheap last-minute flights

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American Airlines flights from Winnipeg to Chicago

Our best American Airlines deals on Winnipeg to Chicago flight tickets

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

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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 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.

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