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

Porter Airlines, WestJet, and Air Canada are the most popular carriers 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 46% 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 August 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 62% of daily flights taking off at noon.

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

As of August 2026, there are 48 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 August 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$ 246 Cheap Flights from Winnipeg to Chicago in 2026

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Find the cheapest flights from Winnipeg to Chicago

Round-trip

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Cheap round-trip flights

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6:05 p.m. - 11:00 a.m.YWG Winnipeg-MDW Chicago Midway

16h 55m1 stop Toronto Pearson Intl

11:45 a.m. - 12:55 a.m.MDW Chicago Midway-YWG Winnipeg

13h 10m1 stop Toronto Island

C$ 457Multiple Airlines

Wed, 23 Sep - Sun, 4 Oct

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

23h 45m2 stops Montreal St Hubert Toronto Pearson Intl

3:20 p.m. - 9:45 a.m.MDW Chicago Midway-YWG Winnipeg

18h 25m1 stop Toronto Island

C$ 464Multiple Airlines

Wed, 23 Sep - Sun, 4 Oct

11:15 a.m. - 7:48 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

8h 33m2 stops Montreal St Hubert Toronto Pearson Intl

9:50 a.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

15h 05m1 stop Toronto Pearson Intl

C$ 503Multiple Airlines

Fri, 18 Sep - Fri, 25 Sep

7:10 p.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

21h 30m1 stop Calgary

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

7h 25m1 stop Calgary

C$ 509WestJet

Fri, 28 Aug - Mon, 31 Aug

9:05 p.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

19h 35m1 stop Calgary

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

7h 25m1 stop Calgary

C$ 514WestJet

Fri, 28 Aug - Tue, 1 Sep

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

9h 40m1 stop Calgary

5:30 p.m. - 3:25 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

21h 55m1 stop Calgary

C$ 521WestJet

Wed, 2 Sep - Thu, 3 Sep

12:20 p.m. - 7:48 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

7h 28m1 stop Toronto Pearson Intl

9:50 a.m. - 4:17 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

6h 27m1 stop Toronto Pearson Intl

C$ 686Air Canada

Tue, 13 Oct - Wed, 21 Oct

12:20 p.m. - 7:48 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

7h 28m1 stop Toronto Pearson Intl

2:15 p.m. - 9:27 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 12m1 stop Toronto Pearson Intl

C$ 691Air Canada

Thu, 10 Sep - Sat, 12 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$ 956United Airlines

Wed, 7 Oct - Sun, 11 Oct

2:15 p.m. - 4:36 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 21mdirect

9:15 a.m. - 11:39 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 24mdirect

C$ 956United Airlines

Thu, 14 Jan - Tue, 19 Jan

Cheap last-minute flights

Enter your travel dates to find the best prices.

5:10 p.m. - 9:00 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

15h 50m1 stop Toronto Pearson Intl

5:35 p.m. - 8:40 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

15h 05m1 stop Toronto Pearson Intl

C$ 905Multiple Airlines

Tue, 11 Aug - Tue, 18 Aug

9:05 p.m. - 8:05 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

23h 00m3 stops Calgary Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

5:35 p.m. - 8:40 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

15h 05m1 stop Toronto Pearson Intl

C$ 966Multiple Airlines

Tue, 11 Aug - Tue, 18 Aug

2:55 p.m. - 9:00 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

18h 05m2 stops Calgary Toronto Pearson Intl

5:35 p.m. - 8:40 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

15h 05m1 stop Toronto Pearson Intl

C$ 981Multiple Airlines

Tue, 11 Aug - Tue, 18 Aug

6:40 a.m. - 1:10 p.m.YWG Winnipeg-MDW Chicago Midway

6h 30m1 stop Minneapolis St Paul

9:59 a.m. - 4:52 p.m.MDW Chicago Midway-YWG Winnipeg

6h 53m1 stop Minneapolis St Paul

C$ 1,056WestJet

Tue, 11 Aug - Tue, 18 Aug

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$ 1,166Air Canada

Tue, 11 Aug - Tue, 18 Aug

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

2h 35mdirect

12:45 p.m. - 8:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 12m1 stop Denver Intl

C$ 1,184Air Canada

Tue, 11 Aug - Tue, 18 Aug

6:05 p.m. - 4:15 p.m.YWG Winnipeg-MDW Chicago Midway

22h 10m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

9:59 a.m. - 4:52 p.m.MDW Chicago Midway-YWG Winnipeg

6h 53m1 stop Minneapolis St Paul

C$ 1,233WestJet

Tue, 11 Aug - Tue, 18 Aug

9:05 p.m. - 8:55 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

23h 50m2 stops Calgary Atlanta Hartsfield-Jackson

8:28 a.m. - 9:40 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

13h 12m2 stops Minneapolis St Paul Edmonton

C$ 1,334WestJet

Mon, 10 Aug - Sat, 15 Aug

5:00 a.m. - 6:18 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

13h 18m1 stop Toronto Pearson Intl

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

2h 37mdirect

C$ 1,451United Airlines

Mon, 10 Aug - Sat, 15 Aug

12:56 p.m. - 3:30 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 34mdirect

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

2h 37mdirect

C$ 1,522Air Canada

Mon, 10 Aug - Sat, 15 Aug

Cheap direct flights

Enter your travel dates to find the best prices.

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$ 864Air Canada

Tue, 13 Oct - Sun, 18 Oct

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$ 864Air Canada

Fri, 18 Sep - Sun, 20 Sep

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$ 867Air Canada

Wed, 18 Nov - Sun, 22 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$ 867Air Canada

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$ 956United Airlines

Sun, 27 Sep - Tue, 29 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$ 956United Airlines

Wed, 7 Oct - Sun, 11 Oct

2:15 p.m. - 4:36 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 21mdirect

9:15 a.m. - 11:39 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 24mdirect

C$ 956United Airlines

Thu, 14 Jan - Tue, 19 Jan

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$ 1,043Multiple Airlines

Fri, 25 Sep - Sun, 27 Sep

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$ 1,043Multiple Airlines

Fri, 11 Sep - Mon, 14 Sep

2:00 p.m. - 4:35 p.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$ 1,053Multiple Airlines

Fri, 4 Sep - Fri, 11 Sep

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WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

WestJet

28 Aug

YWG7:10 p.m.Winnipeg

21h 30m

1 stop

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

31 Aug

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 509

WestJet

28 Aug

YWG9:05 p.m.Winnipeg

19h 35m

1 stop

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

1 Sep

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 514

WestJet

2 Sep

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

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

3 Sep

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

21h 55m

1 stop

YWG3:25 p.m.Winnipeg

C$ 521

United Airlines flights from Winnipeg to Chicago

Our best United Airlines deals on Winnipeg to Chicago flight tickets

United Airlines

19 Aug

YWG8:45 a.m.Winnipeg

15h 14m

1 stop

ORD11:59 p.m.Chicago O'Hare Intl

24 Aug

ORD9:15 a.m.Chicago O'Hare Intl

2h 37m

YWG11:52 a.m.Winnipeg

C$ 1,131

United Airlines

19 Aug

YWG8:45 a.m.Winnipeg

11h 36m

1 stop

ORD8:21 p.m.Chicago O'Hare Intl

23 Aug

ORD9:15 a.m.Chicago O'Hare Intl

2h 37m

YWG11:52 a.m.Winnipeg

C$ 1,132

United Airlines

19 Aug

YWG8:45 a.m.Winnipeg

15h 14m

1 stop

ORD11:59 p.m.Chicago O'Hare Intl

24 Aug

ORD9:15 a.m.Chicago O'Hare Intl

2h 37m

YWG11:52 a.m.Winnipeg

C$ 1,134

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Wed 23/9

6:05 p.m.-11:00 a.m.

1 stop16h 55m

Chicago Midway

Sun 4/10

11:45 a.m.-12:55 a.m.

1 stop13h 10m

C$ 457

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Wed 23/9

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

2 stops23h 45m

Chicago Midway

Sun 4/10

3:20 p.m.-9:45 a.m.

1 stop18h 25m

C$ 464

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 18/9

11:15 a.m.-7:48 p.m.

2 stops8h 33m

Chicago O'Hare Intl

Fri 25/9

9:50 a.m.-12:55 a.m.

1 stop15h 05m

C$ 503

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 28/8

7:10 p.m.-4:40 p.m.

1 stop21h 30m

Chicago O'Hare Intl

Mon 31/8

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

1 stop7h 25m

C$ 509

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 28/8

9:05 p.m.-4:40 p.m.

1 stop19h 35m

Chicago O'Hare Intl

Tue 1/9

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

1 stop7h 25m

C$ 514

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 2/9

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

1 stop9h 40m

Chicago O'Hare Intl

Thu 3/9

5:30 p.m.-3:25 p.m.

1 stop21h 55m

C$ 521

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 13/10

12:20 p.m.-7:48 p.m.

1 stop7h 28m

Chicago O'Hare Intl

Wed 21/10

9:50 a.m.-4:17 p.m.

1 stop6h 27m

C$ 686

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 10/9

12:20 p.m.-7:48 p.m.

1 stop7h 28m

Chicago O'Hare Intl

Sat 12/9

2:15 p.m.-9:27 p.m.

1 stop7h 12m

C$ 691

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 7/10

7:00 a.m.-9:35 a.m.

Nonstop2h 35m

Chicago O'Hare Intl

Sun 11/10

10:00 a.m.-12:37 p.m.

Nonstop2h 37m

C$ 956

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 14/1

2:15 p.m.-4:36 p.m.

Nonstop2h 21m

Chicago O'Hare Intl

Tue 19/1

9:15 a.m.-11:39 a.m.

Nonstop2h 24m

C$ 956

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$ 650 to C$ 1,153.
The lowest price recently found on this route was C$ 457.

What is the cheapest month to fly to Chicago?

The month of October is another great option to travel to Chicago, with average flight prices from Winnipeg averaging around C$ 541.

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$ 811. 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$ 1,164. 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$ 866. 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$ 978 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 28% 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 August 2026, prices for Winnipeg to Chicago flights are approximately 114% 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$ 549
Fastest flight time	2h 21m
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$ 549. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 699.

The fastest flight from Winnipeg to Chicago takes 2h 21m

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 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 August 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) (86.33% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (5.76%), Boeing 737 MAX 8 (2.88%), and Boeing 737-800 Passenger/BBJ2 (winglets) (1.44%).
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 United Airlines (44% of total bookings). The next most popular airlines are Air Canada (30%) and WestJet (25%).

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 3,426 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 492	Free Cancellation	Rating 7.4 10,085 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 712	Free Cancellation	Rating 7.1 11,449 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$ 958, but momondo users have found United Airlines deals from Winnipeg to Chicago from as low as C$ 492 round-trip. United Airlines has been scored 7.4/10 in 10,084 reviews.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.1/10 from 11,438 reviews) operates around 12 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 914, 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

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$ 246

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 25/9. 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

United Airlines flights from Winnipeg to Chicago

Our best United 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.

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

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Complete your trip to Chicago

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According to popular flight searches on momondo this year