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

Porter Airlines is the most popular carrier operating from Winnipeg to Illinois

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

The number of flights available between Winnipeg and Illinois is 5 per week as of October 2026. The most frequent departure day is Fri, with 60% of weekly flights leaving on this day.

When did momondo last update prices for flights from Winnipeg Airport to Illinois?

Prices for flights from Winnipeg Airport to Illinois refresh daily.

How many operators does momondo search for flights from Winnipeg Airport to Illinois?

The number of operators available for flights from Winnipeg Airport to Illinois is 2 as of October 2026.

How old do you have to be to fly from Winnipeg Airport to Illinois?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Illinois.

What documentation or ID do you need to fly to Illinois?

The travel and health documents required for your trip to Illinois 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 Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$203 Cheap Flights from Winnipeg to Illinois in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to Illinois

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:55 pm - 11:35 amYWG Winnipeg-ORD Chicago O'Hare Intl

16h 40m1 stop Toronto Pearson Intl

6:20 pm - 10:15 amORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

$397Multiple Airlines

Mon, Dec 14 - Wed, Dec 16

7:00 am - 11:50 amYWG Winnipeg-ORD Chicago O'Hare Intl

29h 50m1 stop Atlanta Hartsfield-Jackson

6:20 pm - 10:15 amORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

$405Multiple Airlines

Mon, Feb 1 - Thu, Feb 4

9:35 pm - 2:30 pmYWG Winnipeg-ORD Chicago O'Hare Intl

17h 55m2 stops Calgary Atlanta Hartsfield-Jackson

8:30 am - 1:10 amORD Chicago O'Hare Intl-YWG Winnipeg

15h 40m2 stops Atlanta Hartsfield-Jackson Calgary

$407Multiple Airlines

Mon, Dec 14 - Wed, Dec 16

12:40 pm - 11:30 amYWG Winnipeg-ORD Chicago O'Hare Intl

23h 50m2 stops Ottawa Toronto Island

6:20 pm - 10:15 amORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

$413Multiple Airlines

Tue, Jan 19 - Fri, Jan 22

8:15 am - 1:13 pmYWG Winnipeg-ORD Chicago O'Hare Intl

5h 58m1 stop Toronto Pearson Intl

8:50 pm - 11:09 amORD Chicago O'Hare Intl-YWG Winnipeg

13h 19m1 stop Toronto Pearson Intl

$597Air Canada

Tue, Jan 26 - Fri, Jan 29

8:15 am - 3:38 pmYWG Winnipeg-ORD Chicago O'Hare Intl

8h 23m1 stop Toronto Pearson Intl

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

$670Air Canada

Mon, Dec 14 - Wed, Dec 16

3:15 pm - 5:02 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 47mnonstop

10:00 am - 1:52 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 52mnonstop

$679United Airlines

Thu, Dec 17 - Sun, Dec 20

3:15 pm - 5:00 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mnonstop

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

$680United Airlines

Fri, Dec 4 - Sun, Dec 6

8:00 am - 9:31 amYWG Winnipeg-ORD Chicago O'Hare Intl

2h 31mnonstop

3:35 pm - 7:26 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 51mnonstop

$680United Airlines

Thu, Feb 25 - Sun, Feb 28

6:15 am - 11:57 amYWG Winnipeg-ORD Chicago O'Hare Intl

6h 42m1 stop Toronto Pearson Intl

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

$688Air Canada

Thu, Nov 12 - Tue, Nov 17

Cheap last minute flights

Enter your travel dates to find the best prices.

6:00 am - 3:37 pmYWG Winnipeg-ORD Chicago O'Hare Intl

34h 37m2 stops Toronto Pearson Intl Fort Lauderdale

8:15 am - 2:40 pmORD Chicago O'Hare Intl-YWG Winnipeg

29h 25m1 stop Atlanta Hartsfield-Jackson

$680Multiple Airlines

Sun, Nov 1 - Sun, Dec 13

6:00 am - 5:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

12h 40m1 stop Toronto Pearson Intl

6:20 pm - 7:14 pmORD Chicago O'Hare Intl-YWG Winnipeg

23h 54m2 stops Toronto Island Ottawa

$684Multiple Airlines

Tue, Nov 3 - Mon, Nov 30

6:00 am - 5:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

12h 40m1 stop Toronto Pearson Intl

6:20 pm - 12:05 pmORD Chicago O'Hare Intl-YWG Winnipeg

16h 45m1 stop Toronto Island

$698Multiple Airlines

Tue, Nov 3 - Mon, Nov 30

9:05 pm - 11:34 amYWG Winnipeg-ORD Chicago O'Hare Intl

15h 29m1 stop Toronto Pearson Intl

6:20 pm - 7:14 pmORD Chicago O'Hare Intl-YWG Winnipeg

23h 54m2 stops Toronto Island Ottawa

$716Multiple Airlines

Wed, Nov 4 - Mon, Nov 30

9:40 am - 9:30 pmYWG Winnipeg-ORD Chicago O'Hare Intl

12h 50m1 stop Denver Intl

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

$975United Airlines

Sun, Nov 1 - Sun, Dec 13

6:15 am - 11:57 amYWG Winnipeg-ORD Chicago O'Hare Intl

6h 42m1 stop Toronto Pearson Intl

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

$1,037United Airlines

Tue, Nov 3 - Mon, Nov 30

11:20 am - 5:43 pmYWG Winnipeg-ORD Chicago O'Hare Intl

6h 23m1 stop Toronto Pearson Intl

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

$1,076Air Canada

Sat, Oct 31 - Fri, Nov 6

6:15 am - 3:38 pmYWG Winnipeg-ORD Chicago O'Hare Intl

10h 23m1 stop Toronto Pearson Intl

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

$1,097Air Canada

Wed, Nov 4 - Mon, Nov 30

2:15 pm - 4:50 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

1:30 pm - 9:57 pmORD Chicago O'Hare Intl-YWG Winnipeg

7h 27m1 stop Denver Intl

$1,102Air Canada

Sat, Oct 31 - Fri, Nov 6

6:15 am - 7:58 pmYWG Winnipeg-ORD Chicago O'Hare Intl

14h 43m1 stop Toronto Pearson Intl

9:35 am - 1:23 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mnonstop

$1,227United Airlines

Mon, Nov 2 - Mon, Nov 9

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WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets

WestJet

Apr 26

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

May 3

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

$464

WestJet

Nov 12

YWG9:35 pmWinnipeg

13h 50m

2 stops

ORD10:25 amChicago O'Hare Intl

Nov 17

ORD10:32 amChicago O'Hare Intl

29h 53m

2 stops

YWG5:25 pmWinnipeg

$831

United Airlines flights from Winnipeg to Illinois

Our best United Airlines deals on Winnipeg to Illinois flight tickets

United Airlines

Nov 12

YWG3:15 pmWinnipeg

2h 35m

ORD4:50 pmChicago O'Hare Intl

Nov 17

ORD9:35 amChicago O'Hare Intl

2h 48m

YWG1:23 pmWinnipeg

$865

United Airlines

Nov 12

YWG3:15 pmWinnipeg

2h 35m

ORD4:50 pmChicago O'Hare Intl

Nov 17

ORD9:35 amChicago O'Hare Intl

2h 48m

YWG1:23 pmWinnipeg

$910

United Airlines

Nov 12

YWG3:15 pmWinnipeg

2h 35m

ORD4:50 pmChicago O'Hare Intl

Nov 17

ORD9:35 amChicago O'Hare Intl

2h 48m

YWG1:23 pmWinnipeg

$911

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/14

7:55 pm-11:35 am

1 stop16h 40m

Chicago O'Hare Intl

Wed 12/16

6:20 pm-10:15 am

1 stop14h 55m

$397

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 2/1

7:00 am-11:50 am

1 stop29h 50m

Chicago O'Hare Intl

Thu 2/4

6:20 pm-10:15 am

1 stop14h 55m

$405

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/14

9:35 pm-2:30 pm

2 stops17h 55m

Chicago O'Hare Intl

Wed 12/16

8:30 am-1:10 am

2 stops15h 40m

$407

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 1/19

12:40 pm-11:30 am

2 stops23h 50m

Chicago O'Hare Intl

Fri 1/22

6:20 pm-10:15 am

1 stop14h 55m

$413

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 1/26

8:15 am-1:13 pm

1 stop5h 58m

Chicago O'Hare Intl

Fri 1/29

8:50 pm-11:09 am

1 stop13h 19m

$597

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/14

8:15 am-3:38 pm

1 stop8h 23m

Chicago O'Hare Intl

Wed 12/16

9:35 am-1:23 pm

Nonstop2h 48m

$670

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 12/17

3:15 pm-5:02 pm

Nonstop2h 47m

Chicago O'Hare Intl

Sun 12/20

10:00 am-1:52 pm

Nonstop2h 52m

$679

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 12/4

3:15 pm-5:00 pm

Nonstop2h 45m

Chicago O'Hare Intl

Sun 12/6

9:35 am-1:23 pm

Nonstop2h 48m

$680

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 2/25

8:00 am-9:31 am

Nonstop2h 31m

Chicago O'Hare Intl

Sun 2/28

3:35 pm-7:26 pm

Nonstop2h 51m

$680

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 11/12

6:15 am-11:57 am

1 stop6h 42m

Chicago O'Hare Intl

Tue 11/17

9:35 am-1:23 pm

Nonstop2h 48m

$688

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 Illinois

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 Illinois?

The cheapest month to fly to Illinois from Winnipeg is in February. Flight prices, which tend to average around $523, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of February, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $542.

What is the cheapest day to depart on your flight to Illinois?

The cheapest day to depart from Winnipeg to Illinois is on a Saturday when prices can be found for as low as $619. Flights from Winnipeg to Illinois on a Thursday will generally be more expensive and average around $728. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Illinois?

Our most recent data shows that the best time of day to fly to Illinois is in the morning. Flights from Winnipeg to Illinois during this time can be as low as $671. Flights in the afternoon are often more expensive with an average ticket price of $768.

What is the cheapest Winnipeg to Illinois flight route?

Fly from Winnipeg to Chicago O'Hare Intl for the best Winnipeg - Illinois flight prices

What cabin class options are available on Winnipeg to Illinois flights?

There are 4 cabin classes available to choose from on Winnipeg to Illinois 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 Illinois flights?

You could potentially save up to 37% on your flight if you consider stops on a Winnipeg to Illinois flight.

Cheap Winnipeg to Illinois flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Illinois

Best Price Found	$203
Fastest flight time	2h 21m
Direct flights	Every day
Airports in Illinois	98 airports

The best one-way flight to Illinois from Winnipeg in the past 72 hours is $203. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is $397.

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

Direct flights go from Winnipeg to Illinois every day.

There are 98 airports in Illinois. From Winnipeg there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Winnipeg to Illinois

When did momondo last update prices for flights from Winnipeg Airport to Illinois?
Prices for flights from Winnipeg Airport to Illinois refresh daily.
How many operators does momondo search for flights from Winnipeg Airport to Illinois?
The number of operators available for flights from Winnipeg Airport to Illinois is 2 as of October 2026.
How old do you have to be to fly from Winnipeg Airport to Illinois?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Illinois.
What documentation or ID do you need to fly to Illinois?
The travel and health documents required for your trip to Illinois 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 Illinois. 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 Illinois?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Winnipeg to Illinois is Embraer 175 (Enhanced Winglets) (84.67% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (8.76%), Boeing 737-800 Passenger/BBJ2 (winglets) (2.19%), and Boeing 737-700 Passenger/BBJ1 (winglets) (1.46%).

Best airlines flying from Winnipeg to Illinois

Compare and see reviews for airlines that fly from Winnipeg to Illinois with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $517	Free Cancellation	Rating 7.3 10,460 reviews		Search United Airlines flights
Air Canada	PriceFrom $629	Free Cancellation	Rating 7.1 11,835 reviews		Search Air Canada flights

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Illinois?

It is quick and easy to find Winnipeg to Illinois flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Illinois that suits you.

Can I find flights from Winnipeg to Illinois with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Illinois from Winnipeg with this policy.

How can momondo help me find flights from Winnipeg to Illinois?

Once all potential Winnipeg to Illinois flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Winnipeg to Illinois right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Winnipeg to Illinois now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Illinois and let you know when they change.