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

As of June 2026, there are 53 flights per week flying from Illinois to Winnipeg. The most common day of the week flights depart is Wed, with 15% of flights taking off on this day.

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

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

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

7 flights are operational daily from Illinois to Winnipeg as of June 2026. The most popular departure time for this route is 8:00PM, with 63% of flights per day taking off in the evening.

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 June 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.

$197 Cheap Flights from Illinois to Winnipeg in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Illinois to Winnipeg

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

3:20 pm - 12:55 am

ORD

YWG

9h 35m

1 stop

11:15 am - 11:00 am

YWG

ORD

23h 45m

2 stops

$333Multiple Airlines

Tue, Sep 22 - Sat, Sep 26

3:20 pm - 12:55 am

ORD

YWG

9h 35m

1 stop

9:20 am - 11:00 am

YWG

ORD

25h 40m

1 stop

$340Multiple Airlines

Tue, Sep 22 - Sat, Sep 26

3:20 pm - 7:49 pm

ORD

YWG

28h 29m

1 stop

4:15 pm - 11:00 am

YWG

ORD

18h 45m

2 stops

$341Porter Airlines

Sun, Sep 20 - Sat, Sep 26

3:20 pm - 7:49 pm

ORD

YWG

28h 29m

1 stop

9:20 am - 11:00 am

YWG

ORD

25h 40m

1 stop

$347Porter Airlines

Sun, Sep 20 - Sat, Sep 26

9:50 am - 11:20 pm

ORD

YWG

13h 30m

1 stop

11:15 am - 9:35 pm

YWG

ORD

10h 20m

2 stops

$368Multiple Airlines

Fri, Aug 28 - Tue, Sep 8

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

11:15 am - 11:00 am

YWG

ORD

23h 45m

2 stops

$377Multiple Airlines

Sun, Sep 6 - Sun, Sep 13

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

9:05 pm - 4:40 pm

YWG

ORD

19h 35m

1 stop

$389WestJet

Sun, Sep 6 - Sun, Sep 13

11:13 am - 11:30 pm

STL

YWG

12h 17m

1 stop

5:42 pm - 11:26 pm

YWG

STL

5h 44m

1 stop

$612WestJet

Thu, Aug 13 - Wed, Aug 19

12:10 pm - 9:14 pm

STL

YWG

9h 04m

1 stop

10:50 am - 6:41 pm

YWG

STL

7h 51m

1 stop

$613Air Canada

Sat, Sep 19 - Tue, Sep 22

8:55 am - 4:27 pm

STL

YWG

7h 32m

1 stop

10:50 am - 6:41 pm

YWG

STL

7h 51m

1 stop

$618Air Canada

Mon, Sep 21 - Wed, Sep 23

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Air Canada flights from Illinois to Winnipeg

Our best Air Canada deals on Illinois to Winnipeg flight tickets

Air Canada

Sep 12

ORD3:45 pmChicago O'Hare Intl

5h 42m

1 stop

YWG9:27 pmWinnipeg

Sep 19

YWG12:20 pmWinnipeg

7h 28m

1 stop

ORD7:48 pmChicago O'Hare Intl

$521

Air Canada

Sep 19

STL12:10 pmLambert-St Louis

9h 04m

1 stop

YWG9:14 pmWinnipeg

Sep 22

YWG10:50 amWinnipeg

7h 51m

1 stop

STL6:41 pmLambert-St Louis

$613

Air Canada

Sep 21

STL8:55 amLambert-St Louis

7h 32m

1 stop

YWG4:27 pmWinnipeg

Sep 23

YWG10:50 amWinnipeg

7h 51m

1 stop

STL6:41 pmLambert-St Louis

$618

Porter Airlines flights from Illinois to Winnipeg

Our best Porter Airlines deals on Illinois to Winnipeg flight tickets

Porter Airlines

Sep 20

ORD3:20 pmChicago O'Hare Intl

28h 29m

1 stop

YWG7:49 pmWinnipeg

Sep 26

YWG4:15 pmWinnipeg

18h 45m

2 stops

ORD11:00 amChicago O'Hare Intl

$341

Porter Airlines

Sep 20

ORD3:20 pmChicago O'Hare Intl

28h 29m

1 stop

YWG7:49 pmWinnipeg

Sep 26

YWG9:20 amWinnipeg

25h 40m

1 stop

ORD11:00 amChicago O'Hare Intl

$347

Porter Airlines

Aug 6

MDW3:15 pmChicago Midway

19h 28m

2 stops

YWG10:43 amWinnipeg

Aug 13

YWG4:15 pmWinnipeg

17h 30m

2 stops

MDW9:45 amChicago Midway

$596

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 9/22

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Sat 9/26

11:15 am-11:00 am

2 stops23h 45m

$333

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 9/22

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Sat 9/26

9:20 am-11:00 am

1 stop25h 40m

$340

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 9/20

3:20 pm-7:49 pm

1 stop28h 29m

Winnipeg

Sat 9/26

4:15 pm-11:00 am

2 stops18h 45m

$341

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 9/20

3:20 pm-7:49 pm

1 stop28h 29m

Winnipeg

Sat 9/26

9:20 am-11:00 am

1 stop25h 40m

$347

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 8/28

9:50 am-11:20 pm

1 stop13h 30m

Winnipeg

Tue 9/8

11:15 am-9:35 pm

2 stops10h 20m

$368

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 9/6

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sun 9/13

11:15 am-11:00 am

2 stops23h 45m

$377

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 9/6

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sun 9/13

9:05 pm-4:40 pm

1 stop19h 35m

$389

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 8/13

11:13 am-11:30 pm

1 stop12h 17m

Winnipeg

Wed 8/19

5:42 pm-11:26 pm

1 stop5h 44m

$612

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 9/19

12:10 pm-9:14 pm

1 stop9h 04m

Winnipeg

Tue 9/22

10:50 am-6:41 pm

1 stop7h 51m

$613

Quickest round-trip

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Mon 9/21

8:55 am-4:27 pm

1 stop7h 32m

Winnipeg

Wed 9/23

10:50 am-6:41 pm

1 stop7h 51m

$618

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 $585. 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 $1,062.

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

The cheapest time of day to fly to Winnipeg is at noon when flights can be purchased for as low as $556. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $844 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

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?

You could potentially save up to 28% 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	$865
Fastest flight time	2h 24m
Direct flights	Every day
Airports in Winnipeg	1 airport

The best flight deal from Illinois to Winnipeg found on momondo in the last 72 hours is $865

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

Direct flights go from Illinois to Winnipeg every day.

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 June 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 77.65% of the total bookings. Other popular models include Boeing 777-300ER with 5.88%, Boeing 787-10 Dreamliner with 4.71%, and Boeing 777-300 with 4.71%.

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 $208	Free Cancellation	Rating 7.2 3,384 reviews		Search WestJet flights
United Airlines	PriceFrom $362	Free Cancellation	Rating 7.4 9,890 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.