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 60% of daily flights taking off at noon.

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.

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

WestJet and Porter Airlines are the most popular carriers operating from Winnipeg to Chicago

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

As of September 2026, there are 47 flights per week flying from Winnipeg to Chicago. The most common day of the week flights depart is Mon, with 17% 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 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$ 228 Cheap Flights from Winnipeg to Chicago in 2026

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

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4:15 p.m. - 11:00 a.m.YWG Winnipeg-MDW Chicago Midway

18h 45m2 stops Ottawa Toronto Pearson Intl

3:20 p.m. - 12:55 a.m.MDW Chicago Midway-YWG Winnipeg

9h 35m1 stop Toronto Island

C$ 447Multiple Airlines

Sat, 3 Oct - Sun, 4 Oct

4:25 p.m. - 11:00 a.m.YWG Winnipeg-MDW Chicago Midway

18h 35m1 stop Toronto Pearson Intl

3:20 p.m. - 12:55 a.m.MDW Chicago Midway-YWG Winnipeg

9h 35m1 stop Toronto Island

C$ 453Multiple Airlines

Sat, 3 Oct - Sun, 4 Oct

7:55 p.m. - 11:00 a.m.YWG Winnipeg-MDW Chicago Midway

15h 05m1 stop Toronto Pearson Intl

3:20 p.m. - 12:55 a.m.MDW Chicago Midway-YWG Winnipeg

9h 35m1 stop Toronto Island

C$ 460Multiple Airlines

Fri, 2 Oct - Sun, 4 Oct

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$ 612WestJet

Thu, 8 Oct - Sun, 11 Oct

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

30h 30m1 stop Calgary

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

7h 25m1 stop Calgary

C$ 642WestJet

Sun, 4 Oct - Thu, 8 Oct

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. - 4:27 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

6h 32m1 stop Toronto Pearson Intl

C$ 685Air Canada

Wed, 30 Sep - Wed, 7 Oct

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$ 708WestJet

Thu, 1 Oct - Sun, 4 Oct

12:45 p.m. - 8:48 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

8h 03m1 stop Toronto Pearson Intl

1:55 p.m. - 12:24 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

10h 29m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

C$ 838Air Canada

Tue, 17 Nov - Mon, 18 Jan

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

2h 35mdirect

10:55 a.m. - 8:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

10h 02m1 stop Denver Intl

C$ 984United Airlines

Fri, 16 Oct - Tue, 20 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$ 984United Airlines

Mon, 23 Nov - Wed, 2 Dec

Cheap last-minute flights

Enter your travel dates to find the best prices.

9:05 p.m. - 6:23 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

21h 18m2 stops Calgary Atlanta Hartsfield-Jackson

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

7h 25m1 stop Calgary

C$ 763Multiple Airlines

Thu, 10 Sep - Tue, 15 Sep

9:20 a.m. - 4:18 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

6h 58m1 stop Toronto Pearson Intl

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

7h 25m1 stop Calgary

C$ 935Multiple Airlines

Thu, 10 Sep - Tue, 15 Sep

4:55 p.m. - 12:06 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

31h 11m3 stops Calgary Puerto Vallarta Ordaz León Del Bajio

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

7h 25m1 stop Calgary

C$ 1,048Multiple Airlines

Thu, 10 Sep - Tue, 15 Sep

9:05 p.m. - 10:44 p.m.YWG Winnipeg-MDW Chicago Midway

25h 39m2 stops Calgary 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$ 1,077WestJet

Thu, 10 Sep - Sun, 13 Sep

9:05 p.m. - 10:44 p.m.YWG Winnipeg-MDW Chicago Midway

25h 39m2 stops Calgary Atlanta Hartsfield-Jackson

7:13 p.m. - 11:30 p.m.MDW Chicago Midway-YWG Winnipeg

4h 17m1 stop Minneapolis St Paul

C$ 1,087WestJet

Thu, 10 Sep - Sun, 13 Sep

6:40 a.m. - 1:20 p.m.YWG Winnipeg-MDW Chicago Midway

6h 40m1 stop Minneapolis St Paul

7:13 p.m. - 11:30 p.m.MDW Chicago Midway-YWG Winnipeg

4h 17m1 stop Minneapolis St Paul

C$ 1,096WestJet

Thu, 10 Sep - Sun, 13 Sep

4:55 p.m. - 12:06 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

31h 11m3 stops Calgary Puerto Vallarta Ordaz León Del Bajio

5:30 p.m. - 9:20 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

15h 50m2 stops Calgary Edmonton

C$ 1,256Multiple Airlines

Thu, 10 Sep - Tue, 15 Sep

4:55 p.m. - 12:06 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

31h 11m3 stops Calgary Puerto Vallarta Ordaz León Del Bajio

5:30 p.m. - 12:00 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

18h 30m3 stops Calgary Grande Prairie Edmonton

C$ 1,318Multiple Airlines

Thu, 10 Sep - Tue, 15 Sep

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

2h 35mdirect

4:38 p.m. - 11:27 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

6h 49m1 stop Toronto Pearson Intl

C$ 1,405Air Canada

Thu, 10 Sep - Tue, 15 Sep

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

2h 35mdirect

9:15 a.m. - 11:52 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

C$ 1,459Air Canada

Thu, 10 Sep - Tue, 15 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$ 984United Airlines

Wed, 18 Nov - Sun, 22 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$ 984United Airlines

Mon, 23 Nov - Wed, 2 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$ 984United Airlines

Sun, 22 Nov - Wed, 2 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$ 984United Airlines

Mon, 23 Nov - Tue, 1 Dec

2:00 p.m. - 4:35 p.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$ 989Lufthansa

Sat, 3 Oct - Sun, 4 Oct

2:00 p.m. - 4:35 p.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$ 1,067Air Canada

Wed, 30 Sep - Sun, 4 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$ 1,067Air Canada

Mon, 23 Nov - Tue, 1 Dec

2:15 p.m. - 5:02 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 47mdirect

10:00 a.m. - 12:52 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 52mdirect

C$ 1,080Air Canada

Wed, 30 Dec - Sat, 2 Jan

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$ 1,085Multiple Airlines

Fri, 4 Dec - Tue, 8 Dec

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$ 1,085Multiple Airlines

Fri, 16 Oct - Tue, 20 Oct

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WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

WestJet

8 Oct

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

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

11 Oct

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 612

WestJet

4 Oct

YWG10:10 a.m.Winnipeg

30h 30m

1 stop

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

8 Oct

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 642

WestJet

1 Oct

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

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

4 Oct

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 708

Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets

Porter Airlines

7 Nov

YWG11:40 a.m.Winnipeg

24h 00m

2 stops

ORD11:40 a.m.Chicago O'Hare Intl

21 Nov

ORD6:20 p.m.Chicago O'Hare Intl

16h 25m

1 stop

YWG10:45 a.m.Winnipeg

C$ 500

Porter Airlines

7 Nov

YWG7:05 p.m.Winnipeg

16h 35m

1 stop

ORD11:40 a.m.Chicago O'Hare Intl

19 Nov

ORD12:20 p.m.Chicago O'Hare Intl

9h 37m

1 stop

YWG9:57 p.m.Winnipeg

C$ 504

Porter Airlines

17 Sep

YWG9:20 a.m.Winnipeg

6h 58m

1 stop

ORD4:18 p.m.Chicago O'Hare Intl

22 Sep

ORD11:42 a.m.Chicago O'Hare Intl

8h 07m

1 stop

YWG7:49 p.m.Winnipeg

C$ 675

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Sat 3/10

4:15 p.m.-11:00 a.m.

2 stops18h 45m

Chicago Midway

Sun 4/10

3:20 p.m.-12:55 a.m.

1 stop9h 35m

C$ 447

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Sat 3/10

4:25 p.m.-11:00 a.m.

1 stop18h 35m

Chicago Midway

Sun 4/10

3:20 p.m.-12:55 a.m.

1 stop9h 35m

C$ 453

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Fri 2/10

7:55 p.m.-11:00 a.m.

1 stop15h 05m

Chicago Midway

Sun 4/10

3:20 p.m.-12:55 a.m.

1 stop9h 35m

C$ 460

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 8/10

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

1 stop9h 40m

Chicago O'Hare Intl

Sun 11/10

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

1 stop7h 25m

C$ 612

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 4/10

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

1 stop30h 30m

Chicago O'Hare Intl

Thu 8/10

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

1 stop7h 25m

C$ 642

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 30/9

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

1 stop8h 23m

Chicago O'Hare Intl

Wed 7/10

9:55 a.m.-4:27 p.m.

1 stop6h 32m

C$ 685

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 1/10

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

1 stop9h 40m

Chicago O'Hare Intl

Sun 4/10

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

1 stop7h 25m

C$ 708

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 17/11

12:45 p.m.-8:48 p.m.

1 stop8h 03m

Chicago O'Hare Intl

Mon 18/1

1:55 p.m.-12:24 a.m.

2 stops10h 29m

C$ 838

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 16/10

2:00 p.m.-4:35 p.m.

Nonstop2h 35m

Chicago O'Hare Intl

Tue 20/10

10:55 a.m.-8:57 p.m.

1 stop10h 02m

C$ 984

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 23/11

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

Nonstop2h 35m

Chicago O'Hare Intl

Wed 2/12

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

Nonstop2h 48m

C$ 984

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$ 584 to C$ 915.
The lowest price recently found on this route was C$ 447.

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$ 711.

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$ 792. 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$ 1,151. 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$ 869. 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$ 979 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 23% 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 10% 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$ 228
Fastest flight time	2h 35m
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$ 228. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 447.

The fastest flight from Winnipeg to Chicago takes 2h 35m

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 35m 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) (87.50% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (5.26%), Boeing 737 MAX 8 (2.63%), and Boeing 737-800 Passenger/BBJ2 (winglets) (1.32%).
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 (41% of total bookings). The next most popular airlines are United Airlines (35%) 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$ 270	Free Cancellation	Rating 7.2 3,444 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 685	Free Cancellation	Rating 7.4 10,172 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 703	Free Cancellation	Rating 7.1 11,582 reviews	Search Air Canada flights

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$ 956, but momondo users have found United Airlines deals from Winnipeg to Chicago from as low as C$ 685 round-trip. United Airlines has been scored 7.4/10 in 10,165 reviews.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.1/10 from 11,579 reviews) operates around 12 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 868, with deals from around C$ 703 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

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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$ 228

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 18/10. 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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WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets

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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

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