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

6 flights are operational daily from Illinois to Winnipeg as of October 2026. The most popular departure time for this route is 7:00PM, with 53% of flights per day taking off in the evening.

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

As of October 2026, there are 45 flights per week flying from Illinois to Winnipeg. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.

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

Porter Airlines, 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 October 2026, there are 2 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 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Illinois to Winnipeg

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One-way

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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

9:35 pm - 12:51 pmYWG Winnipeg-ORD Chicago O'Hare Intl

15h 16m2 stops Calgary Atlanta Hartsfield-Jackson

$406Multiple Airlines

Fri, Oct 23 - Fri, Oct 30

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

7h 25m1 stop Calgary

9:35 pm - 12:51 pmYWG Winnipeg-ORD Chicago O'Hare Intl

15h 16m2 stops Calgary Atlanta Hartsfield-Jackson

$406Multiple Airlines

Thu, Oct 22 - Fri, Oct 30

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

7h 25m1 stop Calgary

9:35 pm - 12:51 pmYWG Winnipeg-ORD Chicago O'Hare Intl

15h 16m2 stops Calgary Atlanta Hartsfield-Jackson

$406Multiple Airlines

Thu, Oct 22 - Tue, Oct 27

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

7h 25m1 stop Calgary

9:35 pm - 12:51 pmYWG Winnipeg-ORD Chicago O'Hare Intl

15h 16m2 stops Calgary Atlanta Hartsfield-Jackson

$406Multiple Airlines

Fri, Oct 23 - Tue, Oct 27

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

7h 25m1 stop Calgary

5:40 pm - 9:27 pmYWG Winnipeg-ORD Chicago O'Hare Intl

3h 47m1 stop Minneapolis St Paul

$584WestJet

Thu, Oct 22 - Fri, Oct 30

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

7h 25m1 stop Calgary

5:40 pm - 9:27 pmYWG Winnipeg-ORD Chicago O'Hare Intl

3h 47m1 stop Minneapolis St Paul

$584WestJet

Fri, Oct 23 - Fri, Oct 30

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

7h 25m1 stop Calgary

5:40 pm - 9:27 pmYWG Winnipeg-ORD Chicago O'Hare Intl

3h 47m1 stop Minneapolis St Paul

$584WestJet

Fri, Oct 23 - Sat, Oct 31

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

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

11:20 am - 6:57 amYWG Winnipeg-ORD Chicago O'Hare Intl

19h 37m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

$804United Airlines

Mon, Nov 9 - Wed, Nov 11

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

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

11:20 am - 6:57 amYWG Winnipeg-ORD Chicago O'Hare Intl

19h 37m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

$837United Airlines

Tue, Nov 3 - Wed, Nov 11

6:15 pm - 1:49 pmORD Chicago O'Hare Intl-YWG Winnipeg

19h 34m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl

11:20 am - 8:00 amYWG Winnipeg-ORD Chicago O'Hare Intl

20h 40m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

$837United Airlines

Wed, Oct 28 - Wed, Nov 11

Cheap last minute flights

Enter your travel dates to find the best prices.

3:50 pm - 5:58 pmORD Chicago O'Hare Intl-YWG Winnipeg

26h 08m2 stops Orlando Ottawa

5:44 pm - 9:33 pmYWG Winnipeg-ORD Chicago O'Hare Intl

3h 49m1 stop Minneapolis St Paul

$887Multiple Airlines

Thu, Oct 1 - Sun, Oct 4

3:50 pm - 5:58 pmORD Chicago O'Hare Intl-YWG Winnipeg

26h 08m2 stops Orlando Ottawa

5:44 pm - 9:33 pmYWG Winnipeg-ORD Chicago O'Hare Intl

3h 49m1 stop Minneapolis St Paul

$894Multiple Airlines

Thu, Oct 1 - Sun, Oct 4

3:50 pm - 5:58 pmORD Chicago O'Hare Intl-YWG Winnipeg

26h 08m2 stops Orlando Ottawa

5:00 pm - 5:38 amYWG Winnipeg-ORD Chicago O'Hare Intl

12h 38m1 stop Las Vegas Harry Reid Intl

$1,003Multiple Airlines

Thu, Oct 1 - Mon, Oct 5

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

7h 25m1 stop Calgary

12:38 pm - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

4h 02m1 stop Minneapolis St Paul

$1,021WestJet

Fri, Oct 2 - Tue, Oct 6

8:03 am - 3:20 pmORD Chicago O'Hare Intl-YWG Winnipeg

7h 17m1 stop Toronto Pearson Intl

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

9h 40m1 stop Calgary

$1,021Multiple Airlines

Fri, Oct 2 - Tue, Oct 6

10:00 am - 12:37 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mnonstop

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

2h 35mnonstop

$1,300United Airlines

Thu, Oct 1 - Sun, Oct 4

6:10 am - 9:20 amORD Chicago O'Hare Intl-YWG Winnipeg

27h 10m2 stops Minneapolis St Paul Edmonton

7:45 am - 8:30 pmYWG Winnipeg-ORD Chicago O'Hare Intl

12h 45m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

$1,302WestJet

Thu, Oct 1 - Mon, Oct 5

9:59 am - 3:08 pmMDW Chicago Midway-YWG Winnipeg

5h 09m1 stop Minneapolis St Paul

5:40 pm - 4:47 pmYWG Winnipeg-MDW Chicago Midway

23h 07m1 stop Minneapolis St Paul

$1,321WestJet

Fri, Oct 2 - Tue, Oct 6

10:00 am - 12:37 pmORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mnonstop

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

2h 35mnonstop

$1,445United Airlines

Thu, Oct 1 - Sat, Oct 3

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

$1,445United Airlines

Thu, Oct 1 - Fri, Oct 2

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WestJet flights from Illinois to Winnipeg

Our best WestJet deals on Illinois to Winnipeg flight tickets

WestJet

Oct 12

ORD6:00 amChicago O'Hare Intl

5h 48m

1 stop

YWG11:48 amWinnipeg

Oct 15

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

$641

WestJet

Oct 27

MDW12:27 pmChicago Midway

12h 17m

2 stops

YWG12:44 amWinnipeg

Nov 10

YWG5:00 amWinnipeg

13h 04m

2 stops

MDW6:04 pmChicago Midway

$845

WestJet

Oct 27

MDW10:12 amChicago Midway

14h 32m

2 stops

YWG12:44 amWinnipeg

Nov 3

YWG5:00 amWinnipeg

13h 00m

2 stops

MDW6:00 pmChicago Midway

$846

United Airlines flights from Illinois to Winnipeg

Our best United Airlines deals on Illinois to Winnipeg flight tickets

United Airlines

Oct 30

MLI5:00 amMoline Quad-City

7h 23m

1 stop

YWG12:23 pmWinnipeg

Nov 1

YWG2:15 pmWinnipeg

8h 44m

1 stop

MLI10:59 pmMoline Quad-City

$911

United Airlines

Nov 14

MLI5:00 amMoline Quad-City

7h 23m

1 stop

YWG12:23 pmWinnipeg

Nov 21

YWG8:40 amWinnipeg

12h 32m

1 stop

MLI9:12 pmMoline Quad-City

$1,005

United Airlines

Oct 30

MLI10:40 amMoline Quad-City

10h 34m

2 stops

YWG9:14 pmWinnipeg

Nov 1

YWG2:15 pmWinnipeg

8h 44m

1 stop

MLI10:59 pmMoline Quad-City

$1,032

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 10/23

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Fri 10/30

9:35 pm-12:51 pm

2 stops15h 16m

$406

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 10/22

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Fri 10/30

9:35 pm-12:51 pm

2 stops15h 16m

$406

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 10/22

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Tue 10/27

9:35 pm-12:51 pm

2 stops15h 16m

$406

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 10/23

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Tue 10/27

9:35 pm-12:51 pm

2 stops15h 16m

$406

Quickest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 10/22

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Fri 10/30

5:40 pm-9:27 pm

1 stop3h 47m

$584

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 10/23

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Fri 10/30

5:40 pm-9:27 pm

1 stop3h 47m

$584

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 10/23

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sat 10/31

5:40 pm-9:27 pm

1 stop3h 47m

$584

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 11/9

8:03 pm-1:49 pm

2 stops17h 46m

Winnipeg

Wed 11/11

11:20 am-6:57 am

2 stops19h 37m

$804

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 11/3

8:03 pm-1:49 pm

2 stops17h 46m

Winnipeg

Wed 11/11

11:20 am-6:57 am

2 stops19h 37m

$837

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 10/28

6:15 pm-1:49 pm

2 stops19h 34m

Winnipeg

Wed 11/11

11:20 am-8:00 am

2 stops20h 40m

$837

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, October 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 $479. If you’re not able to fly to Winnipeg in October, then March is your next best option. Flight prices from Illinois to Winnipeg during March average around $528.

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 Saturday when prices can be found for as low as $755. 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 $1,315.

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 $844. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $920 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 50% 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	$197
Fastest flight time	2h 37m
Direct flights	Mon, Wed, Thu, Fri, Sat and Sun
Airports in Winnipeg	1 airport

The best one-way flight to Winnipeg from Illinois in the past 72 hours is $197. The best round-trip flight deal from Illinois to Winnipeg found on momondo in the last 72 hours is $406.

The fastest flight from Illinois to Winnipeg takes 2h 37m

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

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 October 2026, there are 2 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 72.00% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 8.00%, Boeing 777-300ER with 8.00%, and Boeing 777-300 with 8.00%.

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 $222	Free Cancellation	Rating 7.2 3,448 reviews		Search WestJet flights
United Airlines	PriceFrom $362	Free Cancellation	Rating 7.4 10,270 reviews		Search United Airlines flights

Selkirk

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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.