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

As of August 2025, there are 54 flights per week flying from Winnipeg to Chicago. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.

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

As of August 2025, 7 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 59% of daily flights taking off at noon.

Which layover airport has the shortest connection time from Winnipeg to Chicago?

Toronto (YYZ) has the shortest average layover time for this route: 1h 26m.

Which layover airport has the shortest travel time from Winnipeg to Chicago?

Flights connecting via Minneapolis (MSP) have the shortest average one-way travel time: 4h 35m.

Which layover airport offers the lowest fares from Winnipeg to Chicago?

Flights via Calgary (YYC) offer the lowest average round-trip price of C$ 443.

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 50% 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.

Which airport is the most popular layover for flights between Winnipeg and Chicago?

Calgary (YYC) was the most common stop: 67% of momondo users choosing one-stop flights on this route connected there.

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

Porter Airlines, United Airlines, and Air Canada 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 August 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$ 243 Cheap Flights from Winnipeg to Chicago in 2025

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

8:30 a.m. - 4:43 p.m.YWG-ORD

8h 13m1 stop

1:40 p.m. - 9:25 p.m.ORD-YWG

7h 45m1 stop

C$ 257WestJet

Find Deal

Tue, 23 Sep - Sat, 27 Sep

8:30 a.m. - 4:43 p.m.YWG-ORD

8h 13m1 stop

5:30 p.m. - 9:01 a.m.ORD-YWG

15h 31m1 stop

C$ 279WestJet

Find Deal

Fri, 17 Oct - Mon, 20 Oct

8:30 a.m. - 4:43 p.m.YWG-ORD

8h 13m1 stop

5:30 p.m. - 9:01 a.m.ORD-YWG

15h 31m1 stop

C$ 281WestJet

Find Deal

Thu, 11 Sep - Mon, 15 Sep

9:00 a.m. - 11:27 a.m.YWG-ORD

26h 27m1 stop

1:40 p.m. - 9:25 p.m.ORD-YWG

7h 45m1 stop

C$ 292

Find Deal

Fri, 26 Sep - Sat, 27 Sep

9:00 a.m. - 11:27 a.m.YWG-ORD

26h 27m1 stop

1:40 p.m. - 9:25 p.m.ORD-YWG

7h 45m1 stop

C$ 303

Find Deal

Fri, 26 Sep - Sat, 27 Sep

8:30 a.m. - 4:43 p.m.YWG-ORD

8h 13m1 stop

5:30 p.m. - 11:26 a.m.ORD-YWG

17h 56m2 stops

C$ 307WestJet

Find Deal

Thu, 16 Oct - Mon, 20 Oct

8:30 a.m. - 4:43 p.m.YWG-ORD

8h 13m1 stop

5:30 p.m. - 11:26 a.m.ORD-YWG

17h 56m2 stops

C$ 311WestJet

Find Deal

Fri, 3 Oct - Mon, 6 Oct

7:00 a.m. - 9:31 a.m.YWG-ORD

2h 31mdirect

7:54 p.m. - 10:33 p.m.ORD-YWG

2h 39mdirect

C$ 460United Airlines

Find Deal

Wed, 8 Oct - Wed, 15 Oct

8:35 a.m. - 5:35 p.m.YWG-MDW

9h 00m1 stop

7:15 p.m. - 11:27 p.m.MDW-YWG

4h 12m1 stop

C$ 494Delta

Find Deal

Tue, 23 Sep - Tue, 30 Sep

6:40 a.m. - 1:03 p.m.YWG-MDW

6h 23m1 stop

7:15 p.m. - 11:27 p.m.MDW-YWG

4h 12m1 stop

C$ 495Delta

Find Deal

Tue, 23 Sep - Fri, 3 Oct

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

WestJet

23 Sep

YWG8:30 a.m.Winnipeg

8h 13m

1 stop

ORD4:43 p.m.Chicago O'Hare Intl

27 Sep

ORD1:40 p.m.Chicago O'Hare Intl

7h 45m

1 stop

YWG9:25 p.m.Winnipeg

C$ 257

Find similar

WestJet

17 Oct

YWG8:30 a.m.Winnipeg

8h 13m

1 stop

ORD4:43 p.m.Chicago O'Hare Intl

20 Oct

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

15h 31m

1 stop

YWG9:01 a.m.Winnipeg

C$ 279

Find similar

WestJet

11 Sep

YWG8:30 a.m.Winnipeg

8h 13m

1 stop

ORD4:43 p.m.Chicago O'Hare Intl

15 Sep

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

15h 31m

1 stop

YWG9:01 a.m.Winnipeg

C$ 281

Find similar

United Airlines flights from Winnipeg to Chicago

Our best United Airlines deals on Winnipeg to Chicago flight tickets

United Airlines

8 Oct

YWG7:00 a.m.Winnipeg

2h 31m

ORD9:31 a.m.Chicago O'Hare Intl

15 Oct

ORD7:54 p.m.Chicago O'Hare Intl

2h 39m

YWG10:33 p.m.Winnipeg

C$ 460

Find similar

United Airlines

29 Aug

YWG7:00 a.m.Winnipeg

2h 31m

ORD9:31 a.m.Chicago O'Hare Intl

6 Sep

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

17h 01m

1 stop

YWG1:09 p.m.Winnipeg

C$ 881

Find similar

United Airlines

1 Sep

YWG2:20 p.m.Winnipeg

2h 31m

ORD4:51 p.m.Chicago O'Hare Intl

5 Sep

ORD9:27 p.m.Chicago O'Hare Intl

15h 42m

1 stop

YWG1:09 p.m.Winnipeg

C$ 969

Find similar

Fly from

Fly to

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 23/9

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Sat 27/9

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 257

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 17/10

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Mon 20/10

5:30 p.m.-9:01 a.m.

1 stop15h 31m

C$ 279

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 11/9

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Mon 15/9

5:30 p.m.-9:01 a.m.

1 stop15h 31m

C$ 281

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 26/9

9:00 a.m.-11:27 a.m.

1 stop26h 27m

Chicago O'Hare Intl

Sat 27/9

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 292

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 26/9

9:00 a.m.-11:27 a.m.

1 stop26h 27m

Chicago O'Hare Intl

Sat 27/9

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 303

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 16/10

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Mon 20/10

5:30 p.m.-11:26 a.m.

2 stops17h 56m

C$ 307

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 3/10

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Mon 6/10

5:30 p.m.-11:26 a.m.

2 stops17h 56m

C$ 311

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 8/10

7:00 a.m.-9:31 a.m.

Nonstop2h 31m

Chicago O'Hare Intl

Wed 15/10

7:54 p.m.-10:33 p.m.

Nonstop2h 39m

C$ 460

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 23/9

8:35 a.m.-5:35 p.m.

1 stop9h 00m

Chicago Midway

Tue 30/9

7:15 p.m.-11:27 p.m.

1 stop4h 12m

C$ 494

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 23/9

6:40 a.m.-1:03 p.m.

1 stop6h 23m

Chicago Midway

Fri 3/10

7:15 p.m.-11:27 p.m.

1 stop4h 12m

C$ 495

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

Layovers

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$ 564.

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$ 813. 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$ 987. 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$ 708. 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$ 860 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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 619 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Winnipeg for as low as C$ 337 on momondo.

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 54% 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 2025, prices for Winnipeg to Chicago flights are approximately 16% 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$ 586
Fastest flight time	2h 21m
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$ 586. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 552.

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

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. 2h 31m 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 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) (73.87% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (5.81%), Boeing 737-700 Passenger/BBJ1 (winglets) (5.16%), and Boeing 737-800 Passenger/BBJ2 (winglets) (3.55%).
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 (40% of total bookings). The next most popular airlines are Air Canada (40%) and WestJet (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$ 200	Free Cancellation	Rating 7.2 3,050 reviews	Search WestJet flights
Air Canada	PriceFrom C$ 361	Free Cancellation	Rating 7.1 10,000 reviews	Search Air Canada flights
United Airlines	PriceFrom C$ 486	Free Cancellation	Rating 7.4 8,940 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$ 453, but momondo users have found United Airlines deals from Winnipeg to Chicago from as low as C$ 352 round-trip. United Airlines has been scored 7.4/10 in 8,940 reviews.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.1/10 from 10,000 reviews) operates around 14 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 432, with deals from around C$ 261 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.

Hammond

Munster

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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Cheap flights from Winnipeg to Chicago from C$ 243

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 9/10. 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

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

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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$ 564.

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

How far in advance should I book a flight to Chicago?

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 54% 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 2025, prices for Winnipeg to Chicago flights are approximately 16% more expensive when compared to flights at the same time last year.

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

Porter Airlines, United Airlines, and Air Canada are the most popular carriers operating from Winnipeg to Chicago

Which airlines fly to Chicago?

Which airport is the most popular layover for flights between Winnipeg and Chicago?

Calgary (YYC) was the most common stop: 67% of momondo users choosing one-stop flights on this route connected there.

Which layover airport offers the lowest fares from Winnipeg to Chicago?

Flights via Calgary (YYC) offer the lowest average round-trip price of C$ 443.

Which layover airport has the shortest travel time from Winnipeg to Chicago?

Flights connecting via Minneapolis (MSP) have the shortest average one-way travel time: 4h 35m.

Which layover airport has the shortest connection time from Winnipeg to Chicago?

Toronto (YYZ) has the shortest average layover time for this route: 1h 26m.

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

As of August 2025, 7 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 59% of daily flights taking off at noon.

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

As of August 2025, there are 54 flights per week flying from Winnipeg to Chicago. The most common day of the week flights depart is Mon, with 15% 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