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 57% 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 June 2026, 8 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 June 2026, there are 56 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?

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

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 June 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$ 1,278 to C$ 972. The lowest price recently found on this route was C$ 509.

Discover deals from 900+ travel sites with momondo.

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.

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$ 509WestJet

Fri, 2 Oct - Sun, 4 Oct

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

YWG

ORD

9h 40m

1 stop

3:20 p.m. - 5:58 p.m.

ORD

YWG

26h 38m

2 stops

C$ 516Multiple Airlines

Thu, 10 Sep - Sun, 13 Sep

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

YWG

ORD

9h 40m

1 stop

7:00 a.m. - 5:58 p.m.

ORD

YWG

10h 58m

2 stops

C$ 517Multiple Airlines

Fri, 4 Sep - Sat, 26 Sep

4:15 p.m. - 9:40 a.m.

YWG

MDW

17h 25m

2 stops

3:20 p.m. - 8:40 a.m.

MDW

YWG

17h 20m

1 stop

C$ 520Multiple Airlines

Sat, 11 Jul - Sun, 12 Jul

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

YWG

ORD

9h 40m

1 stop

7:00 a.m. - 5:58 p.m.

ORD

YWG

10h 58m

2 stops

C$ 520Multiple Airlines

Thu, 17 Sep - Sat, 19 Sep

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$ 522WestJet

Sun, 6 Sep - Mon, 28 Sep

7:50 a.m. - 1:35 p.m.

YWG

ORD

29h 45m

1 stop

2:20 p.m. - 11:55 p.m.

ORD

YWG

9h 35m

1 stop

C$ 529WestJet

Sat, 31 Oct - Fri, 6 Nov

6:35 a.m. - 10:10 p.m.

YWG

MDW

15h 35m

2 stops

6:00 a.m. - 11:34 p.m.

MDW

YWG

17h 34m

2 stops

C$ 646Delta

Sat, 31 Oct - Wed, 4 Nov

6:35 a.m. - 10:10 p.m.

YWG

MDW

15h 35m

2 stops

6:00 a.m. - 11:34 p.m.

MDW

YWG

17h 34m

2 stops

C$ 647Delta

Sat, 31 Oct - Wed, 4 Nov

11:40 a.m. - 9:40 a.m.

YWG

MDW

22h 00m

2 stops

10:25 a.m. - 10:43 a.m.

MDW

YWG

24h 18m

2 stops

C$ 824Porter Airlines

Fri, 3 Jul - Mon, 6 Jul

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Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets

Porter Airlines

4 Sep

YWG11:40 a.m.Winnipeg

8h 40m

2 stops

ORD8:20 p.m.Chicago O'Hare Intl

29 Sep

ORD8:03 a.m.Chicago O'Hare Intl

7h 16m

1 stop

YWG3:19 p.m.Winnipeg

C$ 689

Porter Airlines

4 Sep

YWG11:40 a.m.Winnipeg

8h 40m

2 stops

ORD8:20 p.m.Chicago O'Hare Intl

1 Oct

ORD8:03 a.m.Chicago O'Hare Intl

7h 16m

1 stop

YWG3:19 p.m.Winnipeg

C$ 710

Porter Airlines

3 Jul

YWG11:40 a.m.Winnipeg

22h 00m

2 stops

MDW9:40 a.m.Chicago Midway

6 Jul

MDW10:25 a.m.Chicago Midway

24h 18m

2 stops

YWG10:43 a.m.Winnipeg

C$ 824

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

WestJet

2 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$ 509

WestJet

6 Sep

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

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

28 Sep

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 522

WestJet

31 Oct

YWG7:50 a.m.Winnipeg

29h 45m

1 stop

ORD1:35 p.m.Chicago O'Hare Intl

6 Nov

ORD2:20 p.m.Chicago O'Hare Intl

9h 35m

1 stop

YWG11:55 p.m.Winnipeg

C$ 529

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 2/10

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$ 509

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/9

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

1 stop9h 40m

Chicago O'Hare Intl

Sun 13/9

3:20 p.m.-5:58 p.m.

2 stops26h 38m

C$ 516

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 4/9

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

1 stop9h 40m

Chicago O'Hare Intl

Sat 26/9

7:00 a.m.-5:58 p.m.

2 stops10h 58m

C$ 517

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 11/7

4:15 p.m.-9:40 a.m.

2 stops17h 25m

Chicago Midway

Sun 12/7

3:20 p.m.-8:40 a.m.

1 stop17h 20m

C$ 520

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 17/9

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

1 stop9h 40m

Chicago O'Hare Intl

Sat 19/9

7:00 a.m.-5:58 p.m.

2 stops10h 58m

C$ 520

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 6/9

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 28/9

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

1 stop7h 25m

C$ 522

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 31/10

7:50 a.m.-1:35 p.m.

1 stop29h 45m

Chicago O'Hare Intl

Fri 6/11

2:20 p.m.-11:55 p.m.

1 stop9h 35m

C$ 529

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 31/10

6:35 a.m.-10:10 p.m.

2 stops15h 35m

Chicago Midway

Wed 4/11

6:00 a.m.-11:34 p.m.

2 stops17h 34m

C$ 646

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 31/10

6:35 a.m.-10:10 p.m.

2 stops15h 35m

Chicago Midway

Wed 4/11

6:00 a.m.-11:34 p.m.

2 stops17h 34m

C$ 647

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 3/7

11:40 a.m.-9:40 a.m.

2 stops22h 00m

Chicago Midway

Mon 6/7

10:25 a.m.-10:43 a.m.

2 stops24h 18m

C$ 824

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 November is another great option to travel to Chicago, with average flight prices from Winnipeg averaging around C$ 178.

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$ 842. 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$ 1,165. 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$ 861. 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$ 998 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 42% 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 June 2026, prices for Winnipeg to Chicago flights are approximately 23% 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$ 384
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$ 384. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 773.

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 June 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) (77.32% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (8.25%), Boeing 737 MAX 8 (6.19%), and Boeing 737 MAX 9 (2.06%).
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 (57% of total bookings). The next most popular airlines are WestJet (23%) and Air Canada (20%).

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 3,362 reviews	Search WestJet flights
Air Canada	PriceFrom C$ 369	Free Cancellation	Rating 7.1 11,194 reviews	Search Air Canada flights
United Airlines	PriceFrom C$ 492	Free Cancellation	Rating 7.4 9,831 reviews	Search United Airlines flights

United Airlines Flights From Winnipeg to Chicago
United Airlines operates around 14 flights from Winnipeg to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 799, 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 9,831 reviews.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.1/10 from 11,194 reviews) operates around 14 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 776, with deals from around C$ 369 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 22/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Winnipeg to Chicago

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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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