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

4 flights are operational daily from Winnipeg to Illinois as of March 2026. The most popular departure time for this route is 2:00PM, with 100% of flights per day taking off in the afternoon.

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

The number of flights available between Winnipeg and Illinois is 28 per week as of March 2026. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.

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

Air Canada, Porter Airlines, and WestJet are the most popular carriers operating 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 March 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.

$166 Cheap Flights from Winnipeg to Illinois in 2026

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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 pm

YWG

ORD

9h 40m

1 stop

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

$279WestJet

Fri, Jun 5 - Tue, Jun 9

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

$285WestJet

Sun, May 3 - Thu, May 7

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

5:30 pm - 11:10 am

ORD

YWG

17h 40m

1 stop

$315WestJet

Thu, Apr 30 - Sun, May 3

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

1:59 pm - 3:25 pm

ORD

YWG

25h 26m

2 stops

$322Multiple Airlines

Sun, May 3 - Tue, May 5

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

11:28 am - 3:25 pm

ORD

YWG

27h 57m

2 stops

$333Multiple Airlines

Thu, Apr 30 - Sun, May 3

11:00 am - 8:25 pm

YWG

STL

9h 25m

1 stop

1:05 pm - 11:18 pm

STL

YWG

10h 13m

2 stops

$365Air Canada

Mon, May 4 - Mon, May 11

11:00 am - 8:25 pm

YWG

STL

9h 25m

1 stop

7:05 am - 2:18 pm

STL

YWG

7h 13m

1 stop

$373Air Canada

Sat, May 2 - Sat, May 9

5:20 pm - 11:13 pm

YWG

STL

5h 53m

1 stop

6:20 am - 10:56 am

STL

YWG

4h 36m

1 stop

$376Delta

Sat, Apr 18 - Tue, Apr 21

2:00 pm - 9:52 pm

YWG

STL

7h 52m

1 stop

6:30 am - 11:52 am

STL

YWG

5h 22m

1 stop

$383United Airlines

Sat, Apr 18 - Tue, Apr 21

5:20 pm - 9:56 am

YWG

MDW

16h 36m

2 stops

12:53 pm - 2:55 pm

MDW

YWG

26h 02m

2 stops

$468Delta

Mon, May 4 - Fri, May 8

Air Canada flights from Winnipeg to Illinois

Our best Air Canada deals on Winnipeg to Illinois flight tickets

Air Canada

May 4

YWG11:00 amWinnipeg

9h 25m

1 stop

STL8:25 pmLambert-St Louis

May 11

STL1:05 pmLambert-St Louis

10h 13m

2 stops

YWG11:18 pmWinnipeg

$365

Air Canada

May 4

YWG11:00 amWinnipeg

9h 25m

1 stop

STL8:25 pmLambert-St Louis

May 11

STL7:05 amLambert-St Louis

16h 13m

1 stop

YWG11:18 pmWinnipeg

$388

Air Canada

Apr 3

YWG2:00 pmWinnipeg

2h 35m

ORD4:35 pmChicago O'Hare Intl

Apr 11

ORD8:40 amChicago O'Hare Intl

7h 49m

1 stop

YWG4:29 pmWinnipeg

$803

WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets

WestJet

Jun 5

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

Jun 9

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

$279

WestJet

May 28

YWG7:10 pmWinnipeg

21h 30m

1 stop

ORD4:40 pmChicago O'Hare Intl

May 31

ORD5:30 pmChicago O'Hare Intl

18h 45m

1 stop

YWG12:15 pmWinnipeg

$341

WestJet

Apr 18

YWG5:00 amWinnipeg

11h 42m

2 stops

STL4:42 pmLambert-St Louis

Apr 21

STL5:35 pmLambert-St Louis

17h 21m

1 stop

YWG10:56 amWinnipeg

$405

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 6/5

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 6/9

5:30 pm-12:55 am

1 stop7h 25m

$279

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 5/3

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 5/7

5:30 pm-12:55 am

1 stop7h 25m

$285

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 4/30

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Sun 5/3

5:30 pm-11:10 am

1 stop17h 40m

$315

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 5/3

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 5/5

1:59 pm-3:25 pm

2 stops25h 26m

$322

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 4/30

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Sun 5/3

11:28 am-3:25 pm

2 stops27h 57m

$333

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Mon 5/4

11:00 am-8:25 pm

1 stop9h 25m

Lambert-St Louis

Mon 5/11

1:05 pm-11:18 pm

2 stops10h 13m

$365

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Sat 5/2

11:00 am-8:25 pm

1 stop9h 25m

Lambert-St Louis

Sat 5/9

7:05 am-2:18 pm

1 stop7h 13m

$373

Quickest round-trip

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Sat 4/18

5:20 pm-11:13 pm

1 stop5h 53m

Lambert-St Louis

Tue 4/21

6:20 am-10:56 am

1 stop4h 36m

$376

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Sat 4/18

2:00 pm-9:52 pm

1 stop7h 52m

Lambert-St Louis

Tue 4/21

6:30 am-11:52 am

1 stop5h 22m

$383

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 5/4

5:20 pm-9:56 am

2 stops16h 36m

Chicago Midway

Fri 5/8

12:53 pm-2:55 pm

2 stops26h 02m

$468

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 September. Flight prices, which tend to average around $358, 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 September, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $358.

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

The cheapest day to depart from Winnipeg to Illinois is on a Thursday when prices can be found for as low as $504. Flights from Winnipeg to Illinois on a Sunday will generally be more expensive and average around $797. 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 $607. Flights at noon are often more expensive with an average ticket price of $612.

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 23% 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	$277
Fastest flight time	2h 25m
Direct flights	Every day
Airports in Illinois	98 airports

The best one-way flight to Illinois from Winnipeg in the past 72 hours is $277. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is $500.

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

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

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 March 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) (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%).

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 $199	Free Cancellation	Rating 7.4 9,462 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.