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 47% 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, United Airlines, and Delta are the most popular carriers operating from Winnipeg to Chicago

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

As of October 2025, there are 32 flights per week flying from Winnipeg to Chicago. The most common day of the week flights depart is Wed, with 25% of flights taking off on this day.

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

As of October 2025, 4 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.

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 2025, 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$ 169 Cheap Flights from Winnipeg to Chicago in 2025/26

Q: 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$ 498 to C$ 631. The lowest price recently found on this route was C$ 266.

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Find the cheapest flights from Winnipeg to Chicago

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One-way

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Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:30 a.m. - 10:12 p.m.YWG-MDW

14h 42m1 stop

6:15 a.m. - 3:07 p.m.MDW-YWG

8h 52m1 stop

C$ 266Multiple Airlines

Find Deal

Fri, 5 Dec - Sun, 7 Dec

7:30 a.m. - 10:24 p.m.YWG-ORD

14h 54m1 stop

6:11 a.m. - 3:07 p.m.ORD-YWG

8h 56m1 stop

C$ 267Multiple Airlines

Find Deal

Sun, 7 Dec - Sun, 14 Dec

7:30 a.m. - 10:24 p.m.YWG-ORD

14h 54m1 stop

10:24 a.m. - 12:41 a.m.ORD-YWG

14h 17m2 stops

C$ 276Multiple Airlines

Find Deal

Sun, 7 Dec - Sun, 14 Dec

9:00 p.m. - 12:41 p.m.YWG-MDW

15h 41m2 stops

1:37 p.m. - 3:07 p.m.MDW-YWG

25h 30m1 stop

C$ 284Multiple Airlines

Find Deal

Tue, 11 Nov - Thu, 13 Nov

9:00 p.m. - 9:41 a.m.YWG-MDW

12h 41m2 stops

9:59 a.m. - 4:55 p.m.MDW-YWG

6h 56m1 stop

C$ 589WestJet

Find Deal

Tue, 2 Dec - Tue, 9 Dec

6:40 a.m. - 1:07 p.m.YWG-MDW

6h 27m1 stop

9:41 a.m. - 4:59 p.m.MDW-YWG

7h 18m1 stop

C$ 595WestJet

Find Deal

Sun, 9 Nov - Wed, 12 Nov

5:45 p.m. - 1:08 p.m.YWG-MDW

19h 23m1 stop

9:59 a.m. - 4:55 p.m.MDW-YWG

6h 56m1 stop

C$ 596WestJet

Find Deal

Tue, 2 Dec - Tue, 9 Dec

6:40 a.m. - 1:08 p.m.YWG-MDW

6h 28m1 stop

7:02 p.m. - 11:45 a.m.MDW-YWG

16h 43m1 stop

C$ 603WestJet

Find Deal

Sat, 6 Dec - Sat, 13 Dec

12:35 p.m. - 11:47 p.m.YWG-MDW

11h 12m2 stops

9:29 a.m. - 4:55 p.m.MDW-YWG

7h 26m2 stops

C$ 693Delta

Find Deal

Sat, 6 Dec - Sat, 13 Dec

12:35 p.m. - 11:47 p.m.YWG-MDW

11h 12m2 stops

1:14 p.m. - 11:44 p.m.MDW-YWG

10h 30m2 stops

C$ 762Delta

Find Deal

Fri, 5 Dec - Fri, 12 Dec

Air Canada flights from Winnipeg to Chicago

Our best Air Canada deals on Winnipeg to Chicago flight tickets

Air Canada

4 Nov

YWG5:30 a.m.Winnipeg

7h 31m

1 stop

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

6 Nov

ORD9:22 a.m.Chicago O'Hare Intl

2h 35m

YWG11:57 a.m.Winnipeg

C$ 914

Find similar

Air Canada

2 Nov

YWG8:00 a.m.Winnipeg

9h 10m

1 stop

ORD5:10 p.m.Chicago O'Hare Intl

4 Nov

ORD9:22 a.m.Chicago O'Hare Intl

2h 35m

YWG11:57 a.m.Winnipeg

C$ 1,084

Find similar

Air Canada

28 Oct

YWG6:00 a.m.Winnipeg

6h 51m

1 stop

ORD12:51 p.m.Chicago O'Hare Intl

31 Oct

ORD9:22 a.m.Chicago O'Hare Intl

2h 35m

YWG11:57 a.m.Winnipeg

C$ 1,261

Find similar

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

WestJet

2 Dec

YWG9:00 p.m.Winnipeg

12h 41m

2 stops

MDW9:41 a.m.Chicago Midway

9 Dec

MDW9:59 a.m.Chicago Midway

6h 56m

1 stop

YWG4:55 p.m.Winnipeg

C$ 589

Find similar

WestJet

9 Nov

YWG6:40 a.m.Winnipeg

6h 27m

1 stop

MDW1:07 p.m.Chicago Midway

12 Nov

MDW9:41 a.m.Chicago Midway

7h 18m

1 stop

YWG4:59 p.m.Winnipeg

C$ 595

Find similar

WestJet

2 Dec

YWG5:45 p.m.Winnipeg

19h 23m

1 stop

MDW1:08 p.m.Chicago Midway

9 Dec

MDW9:59 a.m.Chicago Midway

6h 56m

1 stop

YWG4:55 p.m.Winnipeg

C$ 596

Find similar

Fly from

Fly to

Route

Depart

Return

Price

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 5/12

7:30 a.m.-10:12 p.m.

1 stop14h 42m

Chicago Midway

Sun 7/12

6:15 a.m.-3:07 p.m.

1 stop8h 52m

C$ 266

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 7/12

7:30 a.m.-10:24 p.m.

1 stop14h 54m

Chicago O'Hare Intl

Sun 14/12

6:11 a.m.-3:07 p.m.

1 stop8h 56m

C$ 267

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 7/12

7:30 a.m.-10:24 p.m.

1 stop14h 54m

Chicago O'Hare Intl

Sun 14/12

10:24 a.m.-12:41 a.m.

2 stops14h 17m

C$ 276

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 11/11

9:00 p.m.-12:41 p.m.

2 stops15h 41m

Chicago Midway

Thu 13/11

1:37 p.m.-3:07 p.m.

1 stop25h 30m

C$ 284

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 2/12

9:00 p.m.-9:41 a.m.

2 stops12h 41m

Chicago Midway

Tue 9/12

9:59 a.m.-4:55 p.m.

1 stop6h 56m

C$ 589

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 9/11

6:40 a.m.-1:07 p.m.

1 stop6h 27m

Chicago Midway

Wed 12/11

9:41 a.m.-4:59 p.m.

1 stop7h 18m

C$ 595

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 2/12

5:45 p.m.-1:08 p.m.

1 stop19h 23m

Chicago Midway

Tue 9/12

9:59 a.m.-4:55 p.m.

1 stop6h 56m

C$ 596

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 6/12

6:40 a.m.-1:08 p.m.

1 stop6h 28m

Chicago Midway

Sat 13/12

7:02 p.m.-11:45 a.m.

1 stop16h 43m

C$ 603

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 6/12

12:35 p.m.-11:47 p.m.

2 stops11h 12m

Chicago Midway

Sat 13/12

9:29 a.m.-4:55 p.m.

2 stops7h 26m

C$ 693

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 5/12

12:35 p.m.-11:47 p.m.

2 stops11h 12m

Chicago Midway

Fri 12/12

1:14 p.m.-11:44 p.m.

2 stops10h 30m

C$ 762

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?

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$ 522.

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$ 810. 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 Sunday because tickets tend to average around C$ 1,000. 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 afternoon is the cheapest time of day to fly from Winnipeg to Chicago when you can find flight prices for as low as C$ 717. Flying to Chicago in the afternoon 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$ 880 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 3 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 67% 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 2025, prices for Winnipeg to Chicago flights are approximately 1% 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$ 477
Fastest flight time	2h 25m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Winnipeg in the past 72 hours is C$ 477. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 632.

The fastest flight from Winnipeg to Chicago takes 2h 25m

Direct flights go from Winnipeg to Chicago every day.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

How far is Winnipeg to Chicago by plane?
A flight from Winnipeg to Chicago will travel around 1153.0 km. 3h 39m 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 2025, 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) (67.30% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (9.89%), Boeing 737-800 Passenger/BBJ2 (winglets) (5.70%), and Airbus A330-300 (3.42%).
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 (41% of total bookings). The next most popular airlines are Air Canada (38%) and WestJet (21%).

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$ 202	Free Cancellation	Rating 7.2 3,139 reviews	Search WestJet flights
Air Canada	PriceFrom C$ 366	Free Cancellation	Rating 7.1 10,350 reviews	Search Air Canada flights
United Airlines	PriceFrom C$ 493	Free Cancellation	Rating 7.4 8,995 reviews	Search United Airlines flights

United Airlines Flights From Winnipeg to Chicago
United Airlines operates around 8 flights from Winnipeg to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 643, but momondo users have found United Airlines deals from Winnipeg to Chicago from as low as C$ 493 round-trip. United Airlines has been scored 7.4/10 in 8,995 reviews.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.1/10 from 10,350 reviews) operates around 8 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 625, with deals from around C$ 366 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.

Munster

Hammond

Merrillville

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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1 adult

Sat 22/11

Sat 29/11

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Popular Cities in the United States

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Flights to Miamifrom C$ 286

Flights to San Franciscofrom C$ 143

Flights to Honolulufrom C$ 337

Flights to Phoenixfrom C$ 186

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Flights to Houstonfrom C$ 239

Flights to Dallasfrom C$ 287

Cheap flights from Winnipeg to Chicago from C$ 169

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

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

Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last-minute flights

Cheap direct flights

Air Canada flights from Winnipeg to Chicago

Our best Air Canada 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

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

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$ 522.

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?

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 3 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 67% 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 2025, prices for Winnipeg to Chicago flights are approximately 1% cheaper when compared to flights at the same time last year.

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

WestJet, United Airlines, and Delta are the most popular carriers operating from Winnipeg to Chicago

Which airlines fly to Chicago?

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

As of October 2025, 4 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 October 2025, there are 32 flights per week flying from Winnipeg to Chicago. The most common day of the week flights depart is Wed, with 25% of flights taking off on this day.

When to book flights from Winnipeg to Chicago

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

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago

Best price found

Fastest flight time

Direct flights

Airports in Chicago

How far is Winnipeg to Chicago by plane?

When did momondo last update prices for flights from Winnipeg Airport to Chicago?

How many operators does momondo search for flights from Winnipeg Airport to Chicago?

How old do you have to be to fly from Winnipeg Airport to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Winnipeg to Chicago?

What is the most popular airline 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

United Airlines Flights From Winnipeg to Chicago

Air Canada Flights From Winnipeg to Chicago

Travelling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Chicago?

Can I find flights from Winnipeg to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Winnipeg to Chicago?

I’m not ready to book a flight from Winnipeg to Chicago right now. Can momondo alert me if 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.

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