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

The number of flights available between Winnipeg and Illinois is 52 per week as of September 2026. The most frequent departure day is Mon, with 15% of weekly flights leaving on this day.

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

Porter Airlines and Delta are the most popular carriers operating from Winnipeg to Illinois

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

7 flights are operational daily from Winnipeg to Illinois as of September 2026. The most popular departure time for this route is 2:00PM, with 51% of flights per day taking off in the afternoon.

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 1 as of September 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.

$173 Cheap Flights from Winnipeg to Illinois in 2026

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.

7:00 am - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

5:30 pm - 11:10 amORD Chicago O'Hare Intl-YWG Winnipeg

17h 40m1 stop Calgary

$338WestJet

Sun, Oct 18 - Mon, Oct 19

7:00 am - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

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

23h 50m2 stops Toronto Island Ottawa

$345Multiple Airlines

Fri, Oct 23 - Mon, Oct 26

7:00 am - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

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

23h 50m2 stops Toronto Island Ottawa

$345Multiple Airlines

Thu, Oct 22 - Mon, Oct 26

4:55 pm - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

23h 45m1 stop Calgary

5:30 pm - 12:55 amORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

$350WestJet

Wed, Oct 21 - Fri, Oct 23

4:15 pm - 11:40 amYWG Winnipeg-ORD Chicago O'Hare Intl

19h 25m2 stops Ottawa Toronto Pearson Intl

6:20 pm - 9:15 amORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

$350Multiple Airlines

Sat, Oct 24 - Sun, Oct 25

9:20 am - 11:40 amYWG Winnipeg-ORD Chicago O'Hare Intl

26h 20m1 stop Toronto Pearson Intl

6:20 pm - 10:45 amORD Chicago O'Hare Intl-YWG Winnipeg

16h 25m1 stop Toronto Island

$364Porter Airlines

Sat, Oct 24 - Sun, Oct 25

7:00 am - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

5:30 pm - 9:35 amORD Chicago O'Hare Intl-YWG Winnipeg

16h 05m2 stops Calgary Saskatoon

$366WestJet

Sun, Oct 18 - Mon, Oct 19

2:55 pm - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

25h 45m1 stop Calgary

5:30 pm - 11:10 amORD Chicago O'Hare Intl-YWG Winnipeg

17h 40m1 stop Calgary

$369WestJet

Sat, Oct 17 - Mon, Oct 19

8:45 am - 11:44 pmYWG Winnipeg-STL Lambert-St Louis

14h 59m1 stop Denver Intl

5:36 pm - 10:33 pmSTL Lambert-St Louis-YWG Winnipeg

4h 57m1 stop Chicago O'Hare Intl

$561United Airlines

Thu, Oct 1 - Mon, Oct 5

2:15 pm - 11:24 pmYWG Winnipeg-STL Lambert-St Louis

9h 09m1 stop Chicago O'Hare Intl

7:30 am - 12:23 pmSTL Lambert-St Louis-YWG Winnipeg

4h 53m1 stop Chicago O'Hare Intl

$561United Airlines

Wed, Nov 4 - Sat, Nov 7

Cheap last minute flights

Enter your travel dates to find the best prices.

8:10 pm - 2:35 pmYWG Winnipeg-MDW Chicago Midway

18h 25m1 stop Toronto Pearson Intl

3:20 pm - 9:45 amMDW Chicago Midway-YWG Winnipeg

18h 25m1 stop Toronto Island

$642Multiple Airlines

Fri, Sep 18 - Sun, Sep 20

8:10 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

14h 50m1 stop Toronto Pearson Intl

3:20 pm - 10:43 amMDW Chicago Midway-YWG Winnipeg

19h 23m2 stops Toronto Island Ottawa

$658Multiple Airlines

Fri, Sep 18 - Sun, Sep 20

5:10 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

17h 50m1 stop Toronto Pearson Intl

3:20 pm - 8:40 amMDW Chicago Midway-YWG Winnipeg

17h 20m1 stop Toronto Island

$695Multiple Airlines

Thu, Sep 17 - Sat, Sep 19

8:45 am - 11:40 pmYWG Winnipeg-STL Lambert-St Louis

14h 55m1 stop Denver Intl

11:25 am - 10:33 pmSTL Lambert-St Louis-YWG Winnipeg

11h 08m1 stop Chicago O'Hare Intl

$730United Airlines

Fri, Sep 18 - Sat, Sep 19

7:00 am - 5:06 pmYWG Winnipeg-STL Lambert-St Louis

10h 06m1 stop Chicago O'Hare Intl

8:00 am - 10:33 pmSTL Lambert-St Louis-YWG Winnipeg

14h 33m1 stop Chicago O'Hare Intl

$730United Airlines

Sat, Sep 19 - Sun, Sep 20

2:05 pm - 10:59 pmYWG Winnipeg-STL Lambert-St Louis

8h 54m2 stops Toronto Pearson Intl Chicago O'Hare Intl

6:00 am - 11:52 amSTL Lambert-St Louis-YWG Winnipeg

5h 52m1 stop Chicago O'Hare Intl

$752United Airlines

Sat, Sep 19 - Sun, Sep 20

2:00 pm - 7:16 pmYWG Winnipeg-STL Lambert-St Louis

5h 16m1 stop Chicago O'Hare Intl

12:59 pm - 9:27 pmSTL Lambert-St Louis-YWG Winnipeg

8h 28m2 stops Chicago O'Hare Intl Toronto Pearson Intl

$752United Airlines

Fri, Sep 18 - Sat, Sep 19

9:05 pm - 5:51 pmYWG Winnipeg-MDW Chicago Midway

20h 46m2 stops Calgary Atlanta Hartsfield-Jackson

3:20 pm - 8:40 amMDW Chicago Midway-YWG Winnipeg

17h 20m1 stop Toronto Island

$754Multiple Airlines

Thu, Sep 17 - Sat, Sep 19

8:45 pm - 4:18 pmYWG Winnipeg-ORD Chicago O'Hare Intl

19h 33m1 stop Toronto Pearson Intl

8:03 am - 3:19 pmORD Chicago O'Hare Intl-YWG Winnipeg

7h 16m1 stop Toronto Pearson Intl

$760Porter Airlines

Fri, Sep 18 - Sun, Sep 20

5:10 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

17h 50m1 stop Toronto Pearson Intl

3:20 pm - 12:55 amMDW Chicago Midway-YWG Winnipeg

9h 35m1 stop Toronto Island

$762Multiple Airlines

Thu, Sep 17 - Mon, Sep 21

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Air Canada flights from Winnipeg to Illinois

Our best Air Canada deals on Winnipeg to Illinois flight tickets

Air Canada

Oct 13

YWG5:00 amWinnipeg

8h 23m

1 stop

ORD1:23 pmChicago O'Hare Intl

Oct 15

ORD9:55 amChicago O'Hare Intl

8h 17m

1 stop

YWG6:12 pmWinnipeg

$479

Air Canada

Oct 18

YWG5:00 amWinnipeg

8h 23m

1 stop

ORD1:23 pmChicago O'Hare Intl

Oct 20

ORD9:55 amChicago O'Hare Intl

8h 17m

1 stop

YWG6:12 pmWinnipeg

$480

Air Canada

Sep 22

YWG5:00 amWinnipeg

8h 23m

1 stop

ORD1:23 pmChicago O'Hare Intl

Oct 18

ORD10:00 amChicago O'Hare Intl

2h 37m

YWG12:37 pmWinnipeg

$617

Porter Airlines flights from Winnipeg to Illinois

Our best Porter Airlines deals on Winnipeg to Illinois flight tickets

Porter Airlines

Oct 24

YWG9:20 amWinnipeg

26h 20m

1 stop

ORD11:40 amChicago O'Hare Intl

Oct 25

ORD6:20 pmChicago O'Hare Intl

16h 25m

1 stop

YWG10:45 amWinnipeg

$364

Porter Airlines

Nov 19

YWG7:00 amWinnipeg

7h 36m

1 stop

ORD2:36 pmChicago O'Hare Intl

Nov 23

ORD2:50 pmChicago O'Hare Intl

7h 07m

1 stop

YWG9:57 pmWinnipeg

$484

Porter Airlines

Nov 14

YWG7:00 amWinnipeg

7h 37m

1 stop

ORD2:37 pmChicago O'Hare Intl

Dec 14

ORD2:50 pmChicago O'Hare Intl

7h 07m

1 stop

YWG9:57 pmWinnipeg

$486

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 10/18

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 10/19

5:30 pm-11:10 am

1 stop17h 40m

$338

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 10/23

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 10/26

6:20 pm-6:10 pm

2 stops23h 50m

$345

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 10/22

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 10/26

6:20 pm-6:10 pm

2 stops23h 50m

$345

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 10/21

4:55 pm-4:40 pm

1 stop23h 45m

Chicago O'Hare Intl

Fri 10/23

5:30 pm-12:55 am

1 stop7h 25m

$350

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 10/24

4:15 pm-11:40 am

2 stops19h 25m

Chicago O'Hare Intl

Sun 10/25

6:20 pm-9:15 am

1 stop14h 55m

$350

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 10/24

9:20 am-11:40 am

1 stop26h 20m

Chicago O'Hare Intl

Sun 10/25

6:20 pm-10:45 am

1 stop16h 25m

$364

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 10/18

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 10/19

5:30 pm-9:35 am

2 stops16h 05m

$366

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 10/17

2:55 pm-4:40 pm

1 stop25h 45m

Chicago O'Hare Intl

Mon 10/19

5:30 pm-11:10 am

1 stop17h 40m

$369

WinnipegSt. Louis

YWG Winnipeg - STL Lambert-St Louis

YWGSTL

Winnipeg

Thu 10/1

8:45 am-11:44 pm

1 stop14h 59m

Lambert-St Louis

Mon 10/5

5:36 pm-10:33 pm

1 stop4h 57m

$561

Quickest round-trip

WinnipegSt. Louis

YWG Winnipeg - STL Lambert-St Louis

YWGSTL

Winnipeg

Wed 11/4

2:15 pm-11:24 pm

1 stop9h 09m

Lambert-St Louis

Sat 11/7

7:30 am-12:23 pm

1 stop4h 53m

$561

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 November. Flight prices, which tend to average around $487, 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 November, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $515.

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 $602. Flights from Winnipeg to Illinois on a Tuesday will generally be more expensive and average around $793. 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 at noon are often more expensive with an average ticket price of $680.

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 57% 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	$173
Fastest flight time	2h 31m
Direct flights	Every day
Airports in Illinois	98 airports

The best one-way flight to Illinois from Winnipeg in the past 72 hours is $173. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is $338.

The fastest flight from Winnipeg to Illinois takes 2h 31m

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 1 as of September 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) (86.67% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (5.93%), Boeing 737 MAX 8 (2.96%), and Boeing 737-800 Passenger/BBJ2 (winglets) (1.48%).

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 $471	Free Cancellation	Rating 7.4 10,214 reviews		Search United Airlines 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.