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

Flights connecting via Minneapolis (MSP) have the shortest average one-way travel time: 5h 25m.

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

As of December 2025, 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 layover airport offers the lowest fares from Winnipeg to Chicago?

Flights via Calgary (YYC) offer the lowest average round-trip price of C$ 447.

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 December 2025, 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.

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

Calgary (YYC) was the most common stop: 75% of momondo users choosing one-stop flights on this route connected there.

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 December 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$ 176 Cheap Flights from Winnipeg to Chicago in 2025/26

1 adult

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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.

12:55 p.m. - 7:24 p.m.

YWG

MDW

30h 29m2 stops

9:38 a.m. - 3:07 p.m.

MDW

YWG

29h 29m1 stop

C$ 304Multiple Airlines

Sat, 17 Jan - Sat, 24 Jan

9:00 p.m. - 1:37 p.m.

YWG

ORD

16h 37m2 stops

5:40 a.m. - 3:07 p.m.

ORD

YWG

9h 27m1 stop

C$ 325Multiple Airlines

Sat, 24 Jan - Fri, 30 Jan

9:00 p.m. - 10:46 p.m.

YWG

ORD

25h 46m2 stops

9:00 a.m. - 12:36 a.m.

ORD

YWG

15h 36m1 stop

C$ 347Multiple Airlines

Thu, 29 Jan - Mon, 2 Feb

12:55 p.m. - 12:05 p.m.

YWG

MDW

23h 10m2 stops

6:20 a.m. - 3:07 p.m.

MDW

YWG

8h 47m1 stop

C$ 353Multiple Airlines

Mon, 19 Jan - Fri, 23 Jan

9:00 p.m. - 1:35 p.m.

YWG

ORD

16h 35m1 stop

6:20 a.m. - 3:07 p.m.

ORD

YWG

8h 47m1 stop

C$ 381Multiple Airlines

Thu, 15 Jan - Sun, 18 Jan

6:55 p.m. - 1:35 p.m.

YWG

ORD

18h 40m1 stop

2:20 p.m. - 10:07 a.m.

ORD

YWG

19h 47m1 stop

C$ 409WestJet

Thu, 29 Jan - Mon, 2 Feb

9:00 p.m. - 4:43 p.m.

YWG

ORD

19h 43m1 stop

5:30 p.m. - 10:00 a.m.

ORD

YWG

16h 30m1 stop

C$ 416WestJet

Sat, 25 Apr - Thu, 30 Apr

9:00 p.m. - 4:43 p.m.

YWG

ORD

19h 43m1 stop

5:30 p.m. - 11:40 a.m.

ORD

YWG

18h 10m1 stop

C$ 417WestJet

Sat, 25 Apr - Thu, 30 Apr

5:21 p.m. - 8:52 a.m.

YWG

MDW

15h 31m2 stops

7:16 p.m. - 11:38 p.m.

MDW

YWG

4h 22m1 stop

C$ 585Delta

Mon, 26 Jan - Wed, 28 Jan

6:45 a.m. - 6:37 p.m.

YWG

MDW

11h 52m2 stops

2:03 p.m. - 11:35 p.m.

MDW

YWG

9h 32m1 stop

C$ 592WestJet

Tue, 3 Mar - Sun, 8 Mar

Air Canada flights from Winnipeg to Chicago

Our best Air Canada deals on Winnipeg to Chicago flight tickets

Air Canada

25 Apr

YWG2:15 p.m.Winnipeg

2h 21m

ORD4:36 p.m.Chicago O'Hare Intl

30 Apr

ORD9:15 a.m.Chicago O'Hare Intl

2h 24m

YWG11:39 a.m.Winnipeg

C$ 608

Find similar

Air Canada

9 Jan

YWG5:30 a.m.Winnipeg

7h 31m

1 stop

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

11 Jan

ORD9:10 a.m.Chicago O'Hare Intl

2h 47m

YWG11:57 a.m.Winnipeg

C$ 618

Find similar

Air Canada

9 Jan

YWG5:30 a.m.Winnipeg

7h 31m

1 stop

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

11 Jan

ORD8:45 p.m.Chicago O'Hare Intl

13h 14m

1 stop

YWG9:59 a.m.Winnipeg

C$ 621

Find similar

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets

WestJet

29 Jan

YWG6:55 p.m.Winnipeg

18h 40m

1 stop

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

2 Feb

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

19h 47m

1 stop

YWG10:07 a.m.Winnipeg

C$ 409

Find similar

WestJet

25 Apr

YWG9:00 p.m.Winnipeg

19h 43m

1 stop

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

30 Apr

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

16h 30m

1 stop

YWG10:00 a.m.Winnipeg

C$ 416

Find similar

WestJet

25 Apr

YWG9:00 p.m.Winnipeg

19h 43m

1 stop

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

30 Apr

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

18h 10m

1 stop

YWG11:40 a.m.Winnipeg

C$ 417

Find similar

Fly from

Fly to

Route

Depart

Return

Price

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 17/1

12:55 p.m.-7:24 p.m.

2 stops30h 29m

Chicago Midway

Sat 24/1

9:38 a.m.-3:07 p.m.

1 stop29h 29m

C$ 304

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 24/1

9:00 p.m.-1:37 p.m.

2 stops16h 37m

Chicago O'Hare Intl

Fri 30/1

5:40 a.m.-3:07 p.m.

1 stop9h 27m

C$ 325

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 29/1

9:00 p.m.-10:46 p.m.

2 stops25h 46m

Chicago O'Hare Intl

Mon 2/2

9:00 a.m.-12:36 a.m.

1 stop15h 36m

C$ 347

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 19/1

12:55 p.m.-12:05 p.m.

2 stops23h 10m

Chicago Midway

Fri 23/1

6:20 a.m.-3:07 p.m.

1 stop8h 47m

C$ 353

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 15/1

9:00 p.m.-1:35 p.m.

1 stop16h 35m

Chicago O'Hare Intl

Sun 18/1

6:20 a.m.-3:07 p.m.

1 stop8h 47m

C$ 381

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 29/1

6:55 p.m.-1:35 p.m.

1 stop18h 40m

Chicago O'Hare Intl

Mon 2/2

2:20 p.m.-10:07 a.m.

1 stop19h 47m

C$ 409

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

9:00 p.m.-4:43 p.m.

1 stop19h 43m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-10:00 a.m.

1 stop16h 30m

C$ 416

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

9:00 p.m.-4:43 p.m.

1 stop19h 43m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-11:40 a.m.

1 stop18h 10m

C$ 417

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 26/1

5:21 p.m.-8:52 a.m.

2 stops15h 31m

Chicago Midway

Wed 28/1

7:16 p.m.-11:38 p.m.

1 stop4h 22m

C$ 585

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

6:45 a.m.-6:37 p.m.

2 stops11h 52m

Chicago Midway

Sun 8/3

2:03 p.m.-11:35 p.m.

1 stop9h 32m

C$ 592

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 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$ 500.

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$ 812. 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$ 1,019. 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$ 715. 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$ 895 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?

No. A direct flight is the cheapest option for a flight between Winnipeg to Chicago.

How have Winnipeg to Chicago flight prices changed over time?

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$ 393
Fastest flight time	2h 21m
Direct flights	Tue, Wed, Thu, Fri, Sat and Sun
Airports in Chicago	1 airport

The best one-way flight to Chicago from Winnipeg in the past 72 hours is C$ 393. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 842.

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

Direct flights go from Winnipeg to Chicago on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.

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 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 December 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) (49.22% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (13.28%), Boeing 737-800 Passenger/BBJ2 (winglets) (7.03%), and Airbus A330-900neo (6.25%).
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 (34%) and WestJet (25%).

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 3,193 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 491	Free Cancellation	Rating 7.4 9,066 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 501	Free Cancellation	Rating 7.1 10,500 reviews	Search Air Canada 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$ 654, but momondo users have found United Airlines deals from Winnipeg to Chicago from as low as C$ 491 round-trip. United Airlines has been scored 7.4/10 in 9,066 reviews.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.1/10 from 10,500 reviews) operates around 7 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around C$ 736, with deals from around C$ 501 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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Sat 3/1

Sat 10/1

Email me momondo's favourite deals

By creating a price alert you accept our terms of use and privacy policy.

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

Flights to Fort Lauderdalefrom C$ 113

Flights to Orlandofrom C$ 177

Flights to New Yorkfrom C$ 188

Flights to Las Vegasfrom C$ 123

Flights to Los Angelesfrom C$ 158

Flights to Miamifrom C$ 274

Flights to San Franciscofrom C$ 130

Flights to Honolulufrom C$ 308

Flights to Phoenixfrom C$ 160

Flights to Tampafrom C$ 211

Flights to Houstonfrom C$ 207

Flights to Seattlefrom C$ 170

Cheap flights from Winnipeg to Chicago from C$ 176

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 13/1. 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

momondo Fare Finder

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 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$ 500.

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 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?

No. A direct flight is the cheapest option for a flight between Winnipeg to Chicago.

How have Winnipeg to Chicago flight prices changed over time?

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: 75% 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$ 447.

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: 5h 25m.

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 December 2025, 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.

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

As of December 2025, 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.

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