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

As of August 2026, there are 54 flights per week flying from Illinois to Winnipeg. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.

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

WestJet and Porter Airlines 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 August 2026. The most popular departure time for this route is 7:00PM, with 61% 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 August 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.

$134 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.

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

7h 25m1 stop Calgary

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

9h 40m1 stop Calgary

$288WestJet

Tue, Sep 1 - Sat, Sep 5

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

7h 25m1 stop Calgary

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

9h 40m1 stop Calgary

$291WestJet

Thu, Sep 17 - Sun, Sep 20

2:41 pm - 8:15 pmORD Chicago O'Hare Intl-YWG Winnipeg

29h 34m2 stops Denver Intl Calgary

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

9h 40m1 stop Calgary

$299Multiple Airlines

Wed, Sep 2 - Sun, Sep 6

2:41 pm - 8:15 pmORD Chicago O'Hare Intl-YWG Winnipeg

29h 34m2 stops Denver Intl Calgary

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

9h 40m1 stop Calgary

$299Multiple Airlines

Wed, Sep 2 - Thu, Sep 10

2:41 pm - 8:15 pmORD Chicago O'Hare Intl-YWG Winnipeg

29h 34m2 stops Denver Intl Calgary

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

9h 40m1 stop Calgary

$299Multiple Airlines

Wed, Sep 2 - Fri, Sep 11

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

7h 25m1 stop Calgary

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

9h 40m1 stop Calgary

$308WestJet

Mon, Aug 31 - Thu, Sep 10

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

7h 25m1 stop Calgary

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

9h 40m1 stop Calgary

$308WestJet

Tue, Sep 1 - Sun, Sep 6

8:03 pm - 1:49 pmORD Chicago O'Hare Intl-YWG Winnipeg

17h 46m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl

12:45 pm - 11:35 amYWG Winnipeg-ORD Chicago O'Hare Intl

22h 50m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

$720United Airlines

Fri, Nov 13 - Fri, Dec 4

10:51 am - 11:20 pmORD Chicago O'Hare Intl-YWG Winnipeg

12h 29m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

8:15 am - 7:48 pmYWG Winnipeg-ORD Chicago O'Hare Intl

11h 33m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

$886United Airlines

Wed, Sep 2 - Wed, Sep 9

10:51 am - 11:20 pmORD Chicago O'Hare Intl-YWG Winnipeg

12h 29m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

8:15 am - 8:30 pmYWG Winnipeg-ORD Chicago O'Hare Intl

12h 15m2 stops Toronto Pearson Intl Lambert-St Louis

$894United Airlines

Wed, Sep 2 - Sat, Sep 5

Cheap last minute flights

Enter your travel dates to find the best prices.

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

7h 25m1 stop Calgary

5:42 pm - 9:47 pmYWG Winnipeg-ORD Chicago O'Hare Intl

4h 05m1 stop Minneapolis St Paul

$652WestJet

Fri, Aug 21 - Mon, Aug 24

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

7h 25m1 stop Calgary

6:00 am - 9:47 pmYWG Winnipeg-ORD Chicago O'Hare Intl

15h 47m2 stops Calgary Minneapolis St Paul

$755WestJet

Fri, Aug 21 - Mon, Aug 24

11:45 am - 7:49 pmORD Chicago O'Hare Intl-YWG Winnipeg

8h 04m1 stop Toronto Pearson Intl

9:20 am - 4:19 pmYWG Winnipeg-ORD Chicago O'Hare Intl

6h 59m1 stop Toronto Pearson Intl

$797Porter Airlines

Thu, Aug 20 - Thu, Aug 27

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

16h 05m2 stops Calgary Saskatoon

7:00 am - 9:47 pmYWG Winnipeg-ORD Chicago O'Hare Intl

14h 47m2 stops Calgary Minneapolis St Paul

$922WestJet

Fri, Aug 21 - Mon, Aug 24

1:44 pm - 12:55 amORD Chicago O'Hare Intl-YWG Winnipeg

11h 11m2 stops Detroit Metropolitan Wayne County Calgary

7:10 pm - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

21h 30m1 stop Calgary

$936WestJet

Thu, Aug 20 - Thu, Aug 27

7:54 pm - 10:33 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mnonstop

2:00 pm - 4:35 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

$1,026Air Canada

Fri, Aug 21 - Mon, Aug 24

1:55 pm - 8:01 pmORD Chicago O'Hare Intl-YWG Winnipeg

6h 06m1 stop Ottawa

7:00 am - 9:35 amYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

$1,031Air Canada

Fri, Aug 21 - Mon, Aug 24

11:30 am - 12:55 amORD Chicago O'Hare Intl-YWG Winnipeg

13h 25m2 stops New York LaGuardia Toronto Pearson Intl

6:05 pm - 2:09 pmYWG Winnipeg-ORD Chicago O'Hare Intl

20h 04m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

$1,039WestJet

Fri, Aug 21 - Mon, Aug 24

1:55 pm - 8:01 pmORD Chicago O'Hare Intl-YWG Winnipeg

6h 06m1 stop Ottawa

12:20 pm - 7:52 pmYWG Winnipeg-ORD Chicago O'Hare Intl

7h 32m1 stop Toronto Pearson Intl

$1,045Air Canada

Fri, Aug 21 - Mon, Aug 24

7:54 pm - 10:33 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mnonstop

2:00 pm - 4:35 pmYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

$1,263United Airlines

Fri, Aug 21 - Mon, Aug 24

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Porter Airlines flights from Illinois to Winnipeg

Our best Porter Airlines deals on Illinois to Winnipeg flight tickets

Porter Airlines

Sep 10

MDW11:45 amChicago Midway

8h 04m

1 stop

YWG7:49 pmWinnipeg

Sep 13

YWG8:45 pmWinnipeg

14h 15m

1 stop

MDW11:00 amChicago Midway

$390

Porter Airlines

Aug 25

MDW3:15 pmChicago Midway

28h 39m

1 stop

YWG7:54 pmWinnipeg

Sep 1

YWG11:15 amWinnipeg

27h 20m

2 stops

MDW2:35 pmChicago Midway

$510

Porter Airlines

Sep 25

MDW11:45 amChicago Midway

30h 13m

2 stops

YWG5:58 pmWinnipeg

Sep 28

YWG4:15 pmWinnipeg

22h 20m

2 stops

MDW2:35 pmChicago Midway

$614

WestJet flights from Illinois to Winnipeg

Our best WestJet deals on Illinois to Winnipeg flight tickets

WestJet

Sep 1

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

Sep 5

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

$288

WestJet

Sep 17

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

Sep 20

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

$291

WestJet

Aug 31

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

Sep 6

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

$308

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 9/1

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sat 9/5

7:00 am-4:40 pm

1 stop9h 40m

$288

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 9/17

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sun 9/20

7:00 am-4:40 pm

1 stop9h 40m

$291

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 9/2

2:41 pm-8:15 pm

2 stops29h 34m

Winnipeg

Sun 9/6

7:00 am-4:40 pm

1 stop9h 40m

$299

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 9/2

2:41 pm-8:15 pm

2 stops29h 34m

Winnipeg

Thu 9/10

7:00 am-4:40 pm

1 stop9h 40m

$299

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 9/2

2:41 pm-8:15 pm

2 stops29h 34m

Winnipeg

Fri 9/11

7:00 am-4:40 pm

1 stop9h 40m

$299

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 8/31

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Thu 9/10

7:00 am-4:40 pm

1 stop9h 40m

$308

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 9/1

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sun 9/6

7:00 am-4:40 pm

1 stop9h 40m

$308

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 11/13

8:03 pm-1:49 pm

2 stops17h 46m

Winnipeg

Fri 12/4

12:45 pm-11:35 am

2 stops22h 50m

$720

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 9/2

10:51 am-11:20 pm

2 stops12h 29m

Winnipeg

Wed 9/9

8:15 am-7:48 pm

2 stops11h 33m

$886

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 9/2

10:51 am-11:20 pm

2 stops12h 29m

Winnipeg

Sat 9/5

8:15 am-8:30 pm

2 stops12h 15m

$894

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, September 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 $435. If you’re not able to fly to Winnipeg in September, then October is your next best option. Flight prices from Illinois to Winnipeg during October average around $490.

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 $699. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday 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 $1,150.

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 $493. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $877 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 is only 1 cabin class 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 55% 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	$1,042
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 $1,042

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 August 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 70.91% of the total bookings. Other popular models include Boeing 777-300ER with 9.09%, Boeing 787-10 Dreamliner with 7.27%, and Boeing 777-300 with 7.27%.

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 3,432 reviews		Search WestJet flights
United Airlines	PriceFrom $362	Free Cancellation	Rating 7.4 10,104 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.