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

3 flights are operational daily from Illinois to Winnipeg as of May 2026. The most popular departure time for this route is 9:00AM, with 100% of flights per day taking off at noon.

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

As of May 2026, there are 21 flights per week flying from Illinois to Winnipeg. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

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

Porter Airlines, United Airlines, and Air Canada 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 May 2026, there are 3 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.

$158 Cheap Flights from Illinois to Winnipeg in 2026

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Find the cheapest flights from Illinois to Winnipeg

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

7:10 pm - 4:40 pm

YWG

ORD

21h 30m

1 stop

$357WestJet

Fri, Jun 5 - Sun, Jun 7

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

2:55 pm - 4:40 pm

YWG

ORD

25h 45m

1 stop

$360WestJet

Fri, Jun 5 - Sun, Jun 7

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

$362WestJet

Mon, Oct 19 - Fri, Oct 23

5:30 pm - 11:10 am

ORD

YWG

17h 40m

1 stop

6:15 am - 1:35 pm

YWG

ORD

7h 20m

1 stop

$377WestJet

Thu, Oct 22 - Mon, Oct 26

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

2:55 pm - 4:40 pm

YWG

ORD

25h 45m

1 stop

$384WestJet

Fri, Jun 5 - Sun, Jun 7

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

6:00 am - 12:25 pm

YWG

ORD

6h 25m

1 stop

$404Multiple Airlines

Thu, Oct 22 - Tue, Oct 27

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

9:20 am - 7:38 pm

YWG

ORD

10h 18m

1 stop

$411Multiple Airlines

Sat, Jun 6 - Sun, Jun 7

12:10 pm - 9:19 pm

STL

YWG

9h 09m

1 stop

10:55 am - 6:42 pm

YWG

STL

7h 47m

1 stop

$640Air Canada

Sun, Aug 16 - Sat, Aug 22

12:10 pm - 9:19 pm

STL

YWG

9h 09m

1 stop

12:20 pm - 8:07 pm

YWG

STL

7h 47m

1 stop

$645Air Canada

Sat, Aug 22 - Wed, Aug 26

6:21 am - 3:04 pm

STL

YWG

8h 43m

1 stop

5:41 pm - 11:23 pm

YWG

STL

5h 42m

1 stop

$648Delta

Sun, Jun 14 - Fri, Jun 19

Porter Airlines flights from Illinois to Winnipeg

Our best Porter Airlines deals on Illinois to Winnipeg flight tickets

Porter Airlines

Jun 4

MDW10:15 amChicago Midway

9h 34m

1 stop

YWG7:49 pmWinnipeg

Jun 8

YWG8:45 pmWinnipeg

12h 50m

1 stop

MDW9:35 amChicago Midway

$533

Porter Airlines

Jun 26

MDW3:20 pmChicago Midway

26h 43m

2 stops

YWG6:03 pmWinnipeg

Jul 3

YWG4:15 pmWinnipeg

17h 25m

2 stops

MDW9:40 amChicago Midway

$633

Porter Airlines

Jun 24

MDW10:25 amChicago Midway

31h 33m

2 stops

YWG5:58 pmWinnipeg

Jun 28

YWG11:40 amWinnipeg

26h 55m

2 stops

MDW2:35 pmChicago Midway

$644

Air Canada flights from Illinois to Winnipeg

Our best Air Canada deals on Illinois to Winnipeg flight tickets

Air Canada

Aug 16

STL12:10 pmLambert-St Louis

9h 09m

1 stop

YWG9:19 pmWinnipeg

Aug 22

YWG10:55 amWinnipeg

7h 47m

1 stop

STL6:42 pmLambert-St Louis

$640

Air Canada

Aug 22

STL12:10 pmLambert-St Louis

9h 09m

1 stop

YWG9:19 pmWinnipeg

Aug 26

YWG12:20 pmWinnipeg

7h 47m

1 stop

STL8:07 pmLambert-St Louis

$645

Air Canada

Jun 10

STL2:15 pmLambert-St Louis

7h 13m

1 stop

YWG9:28 pmWinnipeg

Jun 20

YWG5:10 amWinnipeg

7h 11m

1 stop

STL12:21 pmLambert-St Louis

$650

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 6/5

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sun 6/7

7:10 pm-4:40 pm

1 stop21h 30m

$357

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 6/5

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sun 6/7

2:55 pm-4:40 pm

1 stop25h 45m

$360

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 10/19

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Fri 10/23

7:00 am-4:40 pm

1 stop9h 40m

$362

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/22

5:30 pm-11:10 am

1 stop17h 40m

Winnipeg

Mon 10/26

6:15 am-1:35 pm

1 stop7h 20m

$377

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 6/5

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sun 6/7

2:55 pm-4:40 pm

1 stop25h 45m

$384

Quickest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/22

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Tue 10/27

6:00 am-12:25 pm

1 stop6h 25m

$404

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 6/6

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sun 6/7

9:20 am-7:38 pm

1 stop10h 18m

$411

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sun 8/16

12:10 pm-9:19 pm

1 stop9h 09m

Winnipeg

Sat 8/22

10:55 am-6:42 pm

1 stop7h 47m

$640

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 8/22

12:10 pm-9:19 pm

1 stop9h 09m

Winnipeg

Wed 8/26

12:20 pm-8:07 pm

1 stop7h 47m

$645

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sun 6/14

6:21 am-3:04 pm

1 stop8h 43m

Winnipeg

Fri 6/19

5:41 pm-11:23 pm

1 stop5h 42m

$648

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, February 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 $62. If you’re not able to fly to Winnipeg in February, then October is your next best option. Flight prices from Illinois to Winnipeg during October average around $81.

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 Tuesday when prices can be found for as low as $584. 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 $1,074.

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 $585. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $762 on average. Flights to Winnipeg from Illinois in the morning 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

Can stopping save me money on Illinois to Winnipeg flights?

You could potentially save up to 19% on your flight if you consider stops on a Illinois to Winnipeg flight.

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	$624
Fastest flight time	2h 24m
Direct flights	Mon, Tue, Wed, Thu, Fri and Sat
Airports in Winnipeg	1 airport

The best one-way flight to Winnipeg from Illinois in the past 72 hours is $624. The best round-trip flight deal from Illinois to Winnipeg found on momondo in the last 72 hours is $755.

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

Direct flights go from Illinois to Winnipeg on Monday, Tuesday, Wednesday, Thursday, Friday and Saturday. Airlines offering direct flights are: United Airlines and Air New Zealand.

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

Search flight deals

Frequently asked questions about flying 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 May 2026, there are 3 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 60.66% of the total bookings. Other popular models include Boeing 777-300ER with 8.20%, Boeing 787-10 Dreamliner with 6.56%, and Boeing 777-300 with 6.56%.

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 3,332 reviews		Search WestJet flights
United Airlines	PriceFrom $291	Free Cancellation	Rating 7.4 9,694 reviews		Search United Airlines flights

Selkirk

Portage la Prairie

Morden

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.