What airlines fly to Winnipeg?

United Airlines, Air Canada and WestJet are the top three most popular airlines that fly to Winnipeg from Illinois according to our data. United Airlines is the first choice among our users, with 69% of people opting to fly with this airline when traveling to Winnipeg. Keep in mind that there are 3 different airlines that fly to Winnipeg on a routine basis, so you have a few additional options to choose from.

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

As of December 2025, there are 18 flights per week flying from Illinois to Winnipeg. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.

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

2 flights are operational daily from Illinois to Winnipeg as of December 2025. The most popular departure time for this route is 9:00AM, with 100% of flights per day taking off at noon.

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

Delta, United Airlines, and WestJet are the most popular carriers operating from Illinois to Winnipeg

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

Prices for flights from Illinois to Winnipeg Airport refresh daily.

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

As of December 2025, there are 4 operators available to choose from for flights from Illinois to Winnipeg Airport.

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

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 Illinois to Winnipeg Airport.

What documentation or ID do you need to fly to Winnipeg Airport?

The travel and health documents you'll need for your trip to Winnipeg Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Winnipeg Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$98 Cheap Flights from Illinois to Winnipeg in 2025/26

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Find the cheapest flights from Illinois to Winnipeg

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

2:53 pm - 3:09 pm

ORD

YWG

24h 16m1 stop

9:00 pm - 1:37 pm

YWG

ORD

16h 37m2 stops

$251Multiple Airlines

Tue, Feb 3 - Sat, Feb 7

5:30 pm - 11:40 am

ORD

YWG

18h 10m1 stop

8:30 am - 4:43 pm

YWG

ORD

8h 13m1 stop

$257WestJet

Mon, May 25 - Mon, Jun 1

5:30 pm - 8:48 pm

ORD

YWG

27h 18m2 stops

8:30 am - 4:43 pm

YWG

ORD

8h 13m1 stop

$262WestJet

Mon, May 25 - Mon, Jun 1

2:20 pm - 10:41 pm

ORD

YWG

8h 21m1 stop

12:40 pm - 1:35 pm

YWG

ORD

24h 55m1 stop

$264WestJet

Fri, Jan 23 - Sun, Jan 25

6:15 am - 12:43 am

ORD

YWG

18h 28m1 stop

8:00 am - 11:22 am

YWG

ORD

27h 22m1 stop

$274Multiple Airlines

Sun, Jan 11 - Mon, Jan 19

6:00 am - 12:40 am

MDW

YWG

18h 40m2 stops

7:30 am - 7:59 pm

YWG

MDW

12h 29m1 stop

$276Multiple Airlines

Fri, Feb 27 - Sun, Mar 1

5:30 pm - 11:33 am

ORD

YWG

18h 03m2 stops

7:00 am - 4:43 pm

YWG

ORD

9h 43m2 stops

$280WestJet

Mon, May 25 - Mon, Jun 1

1:00 pm - 9:19 pm

STL

YWG

8h 19m1 stop

12:15 pm - 8:04 pm

YWG

STL

7h 49m1 stop

$428Air Canada

Thu, May 14 - Wed, May 20

4:05 pm - 11:54 pm

STL

YWG

7h 49m1 stop

7:00 am - 3:29 pm

YWG

STL

8h 29m1 stop

$431Air Canada

Sat, Jan 10 - Sat, Jan 17

6:30 am - 11:57 am

STL

YWG

5h 27m1 stop

2:20 pm - 9:13 pm

YWG

STL

6h 53m1 stop

$432United Airlines

Tue, Jan 13 - Tue, Jan 20

WestJet flights from Illinois to Winnipeg

Our best WestJet deals on Illinois to Winnipeg flight tickets

WestJet

May 25

ORD5:30 pmChicago O'Hare Intl

18h 10m

1 stop

YWG11:40 amWinnipeg

Jun 1

YWG8:30 amWinnipeg

8h 13m

1 stop

ORD4:43 pmChicago O'Hare Intl

$257

Find similar

WestJet

May 25

ORD5:30 pmChicago O'Hare Intl

27h 18m

2 stops

YWG8:48 pmWinnipeg

Jun 1

YWG8:30 amWinnipeg

8h 13m

1 stop

ORD4:43 pmChicago O'Hare Intl

$262

Find similar

WestJet

Jan 23

ORD2:20 pmChicago O'Hare Intl

8h 21m

1 stop

YWG10:41 pmWinnipeg

Jan 25

YWG12:40 pmWinnipeg

24h 55m

1 stop

ORD1:35 pmChicago O'Hare Intl

$264

Find similar

United Airlines flights from Illinois to Winnipeg

Our best United Airlines deals on Illinois to Winnipeg flight tickets

United Airlines

Jan 13

STL6:30 amLambert-St Louis

5h 27m

1 stop

YWG11:57 amWinnipeg

Jan 20

YWG2:20 pmWinnipeg

6h 53m

1 stop

STL9:13 pmLambert-St Louis

$432

Find similar

United Airlines

Jan 12

STL8:05 amLambert-St Louis

13h 39m

2 stops

YWG9:44 pmWinnipeg

Jan 15

YWG7:05 amWinnipeg

8h 24m

1 stop

STL3:29 pmLambert-St Louis

$516

Find similar

United Airlines

Dec 24

ORD9:05 pmChicago O'Hare Intl

26h 49m

2 stops

YWG11:54 pmWinnipeg

Dec 30

YWG2:20 pmWinnipeg

2h 43m

ORD5:03 pmChicago O'Hare Intl

$875

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 2/3

2:53 pm-3:09 pm

1 stop24h 16m

Winnipeg

Sat 2/7

9:00 pm-1:37 pm

2 stops16h 37m

$251

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/25

5:30 pm-11:40 am

1 stop18h 10m

Winnipeg

Mon 6/1

8:30 am-4:43 pm

1 stop8h 13m

$257

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/25

5:30 pm-8:48 pm

2 stops27h 18m

Winnipeg

Mon 6/1

8:30 am-4:43 pm

1 stop8h 13m

$262

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/23

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Sun 1/25

12:40 pm-1:35 pm

1 stop24h 55m

$264

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 1/11

6:15 am-12:43 am

1 stop18h 28m

Winnipeg

Mon 1/19

8:00 am-11:22 am

1 stop27h 22m

$274

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 2/27

6:00 am-12:40 am

2 stops18h 40m

Winnipeg

Sun 3/1

7:30 am-7:59 pm

1 stop12h 29m

$276

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/25

5:30 pm-11:33 am

2 stops18h 03m

Winnipeg

Mon 6/1

7:00 am-4:43 pm

2 stops9h 43m

$280

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 5/14

1:00 pm-9:19 pm

1 stop8h 19m

Winnipeg

Wed 5/20

12:15 pm-8:04 pm

1 stop7h 49m

$428

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 1/10

4:05 pm-11:54 pm

1 stop7h 49m

Winnipeg

Sat 1/17

7:00 am-3:29 pm

1 stop8h 29m

$431

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 1/13

6:30 am-11:57 am

1 stop5h 27m

Winnipeg

Tue 1/20

2:20 pm-9:13 pm

1 stop6h 53m

$432

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 Illinois to Winnipeg

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 Winnipeg?

In general, May is the cheapest month to fly from Illinois to Winnipeg. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $271. If you’re not able to fly to Winnipeg in May, then January is your next best option. Flight prices from Illinois to Winnipeg during January average around $319.

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

The cheapest day to depart on your flight to Winnipeg is on a Thursday when prices can be found for as low as $562. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Illinois because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $648.

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

The cheapest time of day to fly to Winnipeg is in the evening when flights can be purchased for as low as $543. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $635 on average. Flights to Winnipeg from Illinois at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Illinois to Winnipeg flight route?

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

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

There are 2 cabin classes available to choose from on Illinois to Winnipeg 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 Illinois to Winnipeg flights?

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

Cheap Illinois to Winnipeg flight deals and tips

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

Best Price Found	$316
Fastest flight time	2h 24m
Direct flights	Mon, Wed, Thu, Fri, Sat and Sun
Airports in Winnipeg	1 airport

The best flight deal from Illinois to Winnipeg found on momondo in the last 72 hours is $316

The fastest flight from Illinois to Winnipeg takes 2h 24m

Direct flights go from Illinois to Winnipeg on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is United Airlines.

There is 1 airport in Winnipeg. From Illinois there are direct flights to Winnipeg (YWG).

Search flight deals

When did momondo last update prices for flights from Illinois to Winnipeg Airport?
Prices for flights from Illinois to Winnipeg Airport refresh daily.
How many operators does momondo search for flights from Illinois to Winnipeg Airport?
As of December 2025, there are 4 operators available to choose from for flights from Illinois to Winnipeg Airport.
How old do you have to be to fly from Illinois to Winnipeg Airport?
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 Illinois to Winnipeg Airport.
What documentation or ID do you need to fly to Winnipeg Airport?
The travel and health documents you'll need for your trip to Winnipeg Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Winnipeg Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Illinois to Winnipeg?
Based on momondo bookings for flights between Illinois and Winnipeg, the leading plane model is Embraer 175 (Enhanced Winglets), making up 73.42% of the total bookings. Other popular models include Boeing 777-300ER with 6.33%, Boeing 737 MAX 8 with 3.80%, and Airbus A319 with 2.53%.

Best airlines flying from Illinois to Winnipeg

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

Airline	Rating	Free Cancellation	Price
WestJet	PriceFrom $156	Free Cancellation	Rating 7.2 3,202 reviews	Search WestJet flights
Air Canada	PriceFrom $230	Free Cancellation	Rating 7.1 10,525 reviews	Search Air Canada flights
United Airlines	PriceFrom $415	Free Cancellation	Rating 7.4 9,092 reviews	Search United Airlines flights

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Why use momondo?

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

Finding the right flight to Winnipeg from Illinois is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Winnipeg quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Illinois to Winnipeg flights to just show those with flexible booking policies.

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

momondo helps you find the best flight between Illinois and Winnipeg by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Of course. momondo tracks the price of Illinois to Winnipeg flights. All you need is a valid email address and we will do the rest; it is that quick and easy.