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 week?

As of March 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.

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 52% 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 March 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 March 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

1 adult

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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.

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$ 383WestJet

Fri, 5 Jun - Tue, 9 Jun

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

YWG

ORD

21h 30m

1 stop

5:30 p.m. - 12:15 p.m.

ORD

YWG

18h 45m

1 stop

C$ 468WestJet

Thu, 28 May - Sun, 31 May

12:10 p.m. - 8:20 p.m.

YWG

ORD

8h 10m

1 stop

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

ORD

YWG

7h 25m

1 stop

C$ 502Multiple Airlines

Tue, 28 Apr - Thu, 30 Apr

9:20 a.m. - 4:18 p.m.

YWG

ORD

6h 58m

1 stop

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

ORD

YWG

7h 25m

1 stop

C$ 506Multiple Airlines

Wed, 13 May - Fri, 15 May

4:55 p.m. - 5:53 p.m.

YWG

ORD

24h 58m

1 stop

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

ORD

YWG

7h 25m

1 stop

C$ 510Multiple Airlines

Fri, 24 Apr - Mon, 27 Apr

9:05 p.m. - 5:00 p.m.

YWG

ORD

19h 55m

2 stops

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

ORD

YWG

7h 25m

1 stop

C$ 516Multiple Airlines

Tue, 28 Apr - Thu, 30 Apr

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

YWG

ORD

9h 40m

1 stop

7:45 p.m. - 12:55 a.m.

ORD

YWG

29h 10m

2 stops

C$ 530Multiple Airlines

Sun, 3 May - Wed, 6 May

9:00 p.m. - 4:40 p.m.

YWG

ORD

19h 40m

1 stop

4:28 p.m. - 3:25 p.m.

ORD

YWG

22h 57m

2 stops

C$ 541Multiple Airlines

Sat, 25 Apr - Mon, 4 May

2:55 p.m. - 10:46 a.m.

YWG

ORD

19h 51m

3 stops

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

ORD

YWG

7h 25m

1 stop

C$ 550Multiple Airlines

Wed, 13 May - Fri, 15 May

9:00 p.m. - 5:53 p.m.

YWG

ORD

20h 53m

2 stops

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

ORD

YWG

7h 25m

1 stop

C$ 569Multiple Airlines

Fri, 24 Apr - Mon, 27 Apr

Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets

Porter Airlines

28 Apr

YWG12:10 p.m.Winnipeg

8h 10m

1 stop

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

29 Apr

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

7h 24m

1 stop

YWG3:30 p.m.Winnipeg

C$ 689

Porter Airlines

2 Apr

YWG4:25 p.m.Winnipeg

17h 50m

2 stops

MDW10:15 a.m.Chicago Midway

5 Apr

MDW4:05 p.m.Chicago Midway

19h 08m

2 stops

YWG11:13 a.m.Winnipeg

C$ 1,408

Porter Airlines

2 Apr

YWG4:25 p.m.Winnipeg

17h 50m

2 stops

MDW10:15 a.m.Chicago Midway

5 Apr

MDW4:05 p.m.Chicago Midway

19h 08m

2 stops

YWG11:13 a.m.Winnipeg

C$ 1,420

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

WestJet

5 Jun

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

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

9 Jun

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 383

WestJet

28 May

YWG7:10 p.m.Winnipeg

21h 30m

1 stop

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

31 May

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

18h 45m

1 stop

YWG12:15 p.m.Winnipeg

C$ 468

WestJet

18 Apr

YWG11:55 a.m.Winnipeg

6h 16m

1 stop

ORD6:11 p.m.Chicago O'Hare Intl

27 Apr

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 594

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/6

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

1 stop9h 40m

Chicago O'Hare Intl

Tue 9/6

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

1 stop7h 25m

C$ 383

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 28/5

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

1 stop21h 30m

Chicago O'Hare Intl

Sun 31/5

5:30 p.m.-12:15 p.m.

1 stop18h 45m

C$ 468

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 28/4

12:10 p.m.-8:20 p.m.

1 stop8h 10m

Chicago O'Hare Intl

Thu 30/4

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

1 stop7h 25m

C$ 502

Quickest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 13/5

9:20 a.m.-4:18 p.m.

1 stop6h 58m

Chicago O'Hare Intl

Fri 15/5

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

1 stop7h 25m

C$ 506

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 24/4

4:55 p.m.-5:53 p.m.

1 stop24h 58m

Chicago O'Hare Intl

Mon 27/4

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

1 stop7h 25m

C$ 510

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 28/4

9:05 p.m.-5:00 p.m.

2 stops19h 55m

Chicago O'Hare Intl

Thu 30/4

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

1 stop7h 25m

C$ 516

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 3/5

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

1 stop9h 40m

Chicago O'Hare Intl

Wed 6/5

7:45 p.m.-12:55 a.m.

2 stops29h 10m

C$ 530

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

9:00 p.m.-4:40 p.m.

1 stop19h 40m

Chicago O'Hare Intl

Mon 4/5

4:28 p.m.-3:25 p.m.

2 stops22h 57m

C$ 541

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 13/5

2:55 p.m.-10:46 a.m.

3 stops19h 51m

Chicago O'Hare Intl

Fri 15/5

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

1 stop7h 25m

C$ 550

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 24/4

9:00 p.m.-5:53 p.m.

2 stops20h 53m

Chicago O'Hare Intl

Mon 27/4

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

1 stop7h 25m

C$ 569

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 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$ 491.

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$ 755. 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$ 1,035. 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$ 829. 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$ 933 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 8% 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 March 2026, prices for Winnipeg to Chicago flights are approximately 108% 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$ 371
Fastest flight time	2h 25m
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$ 371. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 617.

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

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

How far is Winnipeg to Chicago by plane?
A flight from Winnipeg to Chicago will travel around 1153.0 km. 2h 25m 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 March 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) (41.38% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (17.93%), Boeing 737-800 Passenger/BBJ2 (winglets) (12.41%), and Boeing 737 MAX 8 (11.03%).
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 (52% of total bookings). The next most popular airlines are Air Canada (26%) 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$ 200	Free Cancellation	Rating 7.2 3,300 reviews	Search WestJet flights
Air Canada	PriceFrom C$ 315	Free Cancellation	Rating 7.1 10,835 reviews	Search Air Canada flights
United Airlines	PriceFrom C$ 483	Free Cancellation	Rating 7.4 9,462 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$ 645, but momondo users have found United Airlines deals from Winnipeg to Chicago from as low as C$ 483 round-trip. United Airlines has been scored 7.4/10 in 9,462 reviews.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.1/10 from 10,835 reviews) operates around 7 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 744, with deals from around C$ 315 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.

Merrillville

Munster

Hammond

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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Wed 22/4

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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 3/5. 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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Cheap round-trip flights

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Cheap last-minute 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 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

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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