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 51% 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 April 2026, there are 28 flights per week flying from Winnipeg to Chicago. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

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

WestJet is the most popular carrier operating from Winnipeg to Chicago

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

As of April 2026, 4 flights take off from Winnipeg and land in Chicago each day. The most common flight departure time for this route is 2:00p.m., with 100% of daily flights taking off in the afternoon.

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 April 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$ 249 Cheap Flights from Winnipeg to Chicago in 2026

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$ 785 to C$ 332. The lowest price recently found on this route was C$ 472.

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Find the cheapest flights from Winnipeg to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:00 p.m. - 4:40 p.m.

YWG

ORD

28h 40m

1 stop

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

ORD

YWG

7h 25m

1 stop

C$ 472WestJet

Fri, 22 May - Sun, 24 May

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

YWG

ORD

9h 40m

1 stop

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

ORD

YWG

7h 25m

1 stop

C$ 494WestJet

Tue, 1 Sep - Fri, 4 Sep

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

YWG

ORD

9h 40m

2 stops

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

ORD

YWG

7h 25m

1 stop

C$ 501WestJet

Fri, 22 May - Sun, 24 May

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

YWG

ORD

9h 40m

1 stop

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

ORD

YWG

7h 25m

1 stop

C$ 510WestJet

Tue, 1 Sep - Sat, 5 Sep

6:00 a.m. - 4:40 p.m.

YWG

ORD

10h 40m

1 stop

5:30 p.m. - 11:10 a.m.

ORD

YWG

17h 40m

1 stop

C$ 517WestJet

Thu, 30 Apr - Sun, 3 May

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

YWG

ORD

9h 40m

1 stop

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

ORD

YWG

7h 25m

1 stop

C$ 542WestJet

Tue, 23 Jun - Tue, 30 Jun

9:05 p.m. - 7:55 a.m.

YWG

ORD

34h 50m

2 stops

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

ORD

YWG

7h 25m

1 stop

C$ 543Multiple Airlines

Fri, 15 May - Sun, 24 May

9:05 p.m. - 11:12 a.m.

YWG

MDW

14h 07m

2 stops

3:20 p.m. - 2:25 p.m.

MDW

YWG

23h 05m

1 stop

C$ 546Multiple Airlines

Mon, 1 Jun - Mon, 8 Jun

6:40 a.m. - 10:28 p.m.

YWG

MDW

15h 48m

2 stops

6:38 p.m. - 10:54 a.m.

MDW

YWG

16h 16m

2 stops

C$ 651Delta

Sat, 2 May - Wed, 6 May

6:40 a.m. - 10:28 p.m.

YWG

MDW

15h 48m

2 stops

6:38 p.m. - 10:54 a.m.

MDW

YWG

16h 16m

2 stops

C$ 676Delta

Sat, 2 May - Wed, 6 May

Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets

Porter Airlines

23 Jun

YWG9:20 a.m.Winnipeg

6h 55m

1 stop

ORD4:15 p.m.Chicago O'Hare Intl

30 Jun

ORD8:08 a.m.Chicago O'Hare Intl

7h 11m

1 stop

YWG3:19 p.m.Winnipeg

C$ 704

Porter Airlines

23 Jun

YWG9:20 a.m.Winnipeg

7h 00m

1 stop

ORD4:20 p.m.Chicago O'Hare Intl

30 Jun

ORD8:08 a.m.Chicago O'Hare Intl

7h 11m

1 stop

YWG3:19 p.m.Winnipeg

C$ 715

Porter Airlines

12 May

YWG9:20 a.m.Winnipeg

6h 58m

1 stop

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

16 May

ORD8:06 a.m.Chicago O'Hare Intl

7h 13m

1 stop

YWG3:19 p.m.Winnipeg

C$ 720

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

WestJet

22 May

YWG12:00 p.m.Winnipeg

28h 40m

1 stop

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

24 May

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 472

WestJet

1 Sep

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

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

4 Sep

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 494

WestJet

22 May

YWG7:00 a.m.Winnipeg

9h 40m

2 stops

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

24 May

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 501

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 22/5

12:00 p.m.-4:40 p.m.

1 stop28h 40m

Chicago O'Hare Intl

Sun 24/5

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

1 stop7h 25m

C$ 472

Quickest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 1/9

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

1 stop9h 40m

Chicago O'Hare Intl

Fri 4/9

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

1 stop7h 25m

C$ 494

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 22/5

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

2 stops9h 40m

Chicago O'Hare Intl

Sun 24/5

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

1 stop7h 25m

C$ 501

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 1/9

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

1 stop9h 40m

Chicago O'Hare Intl

Sat 5/9

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

1 stop7h 25m

C$ 510

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 30/4

6:00 a.m.-4:40 p.m.

1 stop10h 40m

Chicago O'Hare Intl

Sun 3/5

5:30 p.m.-11:10 a.m.

1 stop17h 40m

C$ 517

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 23/6

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

1 stop9h 40m

Chicago O'Hare Intl

Tue 30/6

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

1 stop7h 25m

C$ 542

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 15/5

9:05 p.m.-7:55 a.m.

2 stops34h 50m

Chicago O'Hare Intl

Sun 24/5

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

1 stop7h 25m

C$ 543

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 1/6

9:05 p.m.-11:12 a.m.

2 stops14h 07m

Chicago Midway

Mon 8/6

3:20 p.m.-2:25 p.m.

1 stop23h 05m

C$ 546

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 2/5

6:40 a.m.-10:28 p.m.

2 stops15h 48m

Chicago Midway

Wed 6/5

6:38 p.m.-10:54 a.m.

2 stops16h 16m

C$ 651

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 2/5

6:40 a.m.-10:28 p.m.

2 stops15h 48m

Chicago Midway

Wed 6/5

6:38 p.m.-10:54 a.m.

2 stops16h 16m

C$ 676

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$ 495.

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 Friday when prices can be found for as low as C$ 773. 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$ 1,082. 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$ 839. 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$ 946 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 41% 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 April 2026, prices for Winnipeg to Chicago flights are approximately 15% 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$ 414
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$ 414. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 558.

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).

Search flight deals

Frequently asked questions about flying from Winnipeg to Chicago

How far is Winnipeg to Chicago by plane?
A flight from Winnipeg to Chicago will travel around 1153.0 km. 2h 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 April 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) (38.57% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (18.57%), Boeing 737-800 Passenger/BBJ2 (winglets) (12.86%), and Boeing 737 MAX 8 (12.14%).
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 (53% of total bookings). The next most popular airlines are Air Canada (24%) and WestJet (22%).

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 3,320 reviews	Search WestJet flights
Air Canada	PriceFrom C$ 317	Free Cancellation	Rating 7.1 10,916 reviews	Search Air Canada flights
United Airlines	PriceFrom C$ 482	Free Cancellation	Rating 7.4 9,579 reviews	Search United Airlines flights

United Airlines Flights From Winnipeg to Chicago
United Airlines operates around 7 flights from Winnipeg to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 635, but momondo users have found United Airlines deals from Winnipeg to Chicago from as low as C$ 482 round-trip. United Airlines has been scored 7.4/10 in 9,579 reviews.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.1/10 from 10,916 reviews) operates around 7 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 750, with deals from around C$ 317 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.

Merrillville

Hammond

Munster

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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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$ 249

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 27/5. 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

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Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

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Porter Airlines flights from Winnipeg to Chicago

Our best Porter 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 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

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

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

United Airlines Flights From Winnipeg to Chicago

Air Canada Flights From Winnipeg to Chicago

Travelling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

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

Get notified when prices go down

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

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago

Fly your favourite airline to Chicago

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

Cabin classes currently available on flights to Chicago

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

Popular Cities in the United States

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

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According to popular flight searches on momondo this year

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