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

2 flights are operational daily from Winnipeg to Illinois as of October 2026. The most popular departure time for this route is 7:00a.m., with 50% of flights per day taking off at noon.

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

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

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

The number of flights available between Winnipeg and Illinois is 14 per week as of October 2026. The most frequent departure day is Wed, with 29% of weekly flights leaving on this day.

Which airlines fly to Illinois?

United Airlines, Air Canada and WestJet are the top three most popular airlines that fly to Illinois from Winnipeg according to our data. United Airlines is the first choice among our users, with 36% of people opting to fly with this airline when travelling to Illinois. Keep in mind that there are 3 different airlines that fly to Illinois on a routine basis, so you have a few additional options to choose from.

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

Prices for flights from Winnipeg Airport to Illinois are refreshed on a daily basis.

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

As of October 2026, there are 3 operators available to choose from for flights from Winnipeg Airport to Illinois.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Illinois.

What documentation or ID do you need to fly to Illinois?

The travel and health documents you'll need for your trip to Illinois 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 Illinois. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

C$ 296 Cheap Flights from Winnipeg to Illinois in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to Illinois

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

7:55 p.m. - 11:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

16h 40m1 stop Toronto Pearson Intl

6:20 p.m. - 10:15 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

C$ 555Multiple Airlines

Mon, 14 Dec - Wed, 16 Dec

11:40 a.m. - 11:40 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

25h 00m2 stops Ottawa Toronto Island

6:20 p.m. - 10:15 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

C$ 566Multiple Airlines

Tue, 5 Jan - Thu, 7 Jan

7:00 a.m. - 11:50 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

29h 50m1 stop Atlanta Hartsfield-Jackson

6:20 p.m. - 10:15 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

C$ 566Multiple Airlines

Mon, 1 Feb - Thu, 4 Feb

7:00 a.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

5:30 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

C$ 649WestJet

Mon, 26 Apr - Mon, 3 May

3:45 p.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

24h 55m1 stop Calgary

5:30 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

C$ 743WestJet

Sat, 24 Apr - Sun, 2 May

8:15 a.m. - 1:13 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

5h 58m1 stop Toronto Pearson Intl

8:50 p.m. - 11:09 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

13h 19m1 stop Toronto Pearson Intl

C$ 835Air Canada

Tue, 26 Jan - Fri, 29 Jan

9:05 a.m. - 2:52 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

6h 47m1 stop Montreal Pierre Elliott Trudeau Intl

4:30 p.m. - 1:24 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 54m1 stop Toronto Pearson Intl

C$ 934Air Canada

Thu, 25 Feb - Sun, 28 Feb

1:10 p.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

27h 30m2 stops Edmonton Calgary

5:30 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

C$ 937WestJet

Sat, 24 Apr - Sun, 2 May

8:00 a.m. - 9:31 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 31mdirect

3:35 p.m. - 7:26 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 51mdirect

C$ 1,105United Airlines

Thu, 25 Feb - Sun, 28 Feb

3:15 p.m. - 5:02 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 47mdirect

10:00 a.m. - 1:52 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 52mdirect

C$ 1,105United Airlines

Sat, 26 Dec - Sun, 27 Dec

Cheap last-minute flights

Enter your travel dates to find the best prices.

6:00 a.m. - 5:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

12h 40m1 stop Toronto Pearson Intl

6:20 p.m. - 7:14 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

23h 54m2 stops Toronto Island Ottawa

C$ 957Multiple Airlines

Tue, 3 Nov - Mon, 30 Nov

6:00 a.m. - 5:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

12h 40m1 stop Toronto Pearson Intl

6:20 p.m. - 12:05 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

16h 45m1 stop Toronto Island

C$ 976Multiple Airlines

Tue, 3 Nov - Mon, 30 Nov

9:05 p.m. - 11:34 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

15h 29m1 stop Toronto Pearson Intl

6:20 p.m. - 7:14 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

23h 54m2 stops Toronto Island Ottawa

C$ 1,001Multiple Airlines

Wed, 4 Nov - Mon, 30 Nov

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,217Air Canada

Tue, 3 Nov - Thu, 5 Nov

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

2:30 p.m. - 9:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

6h 27m1 stop Denver Intl

C$ 1,231Air Canada

Tue, 3 Nov - Thu, 5 Nov

6:15 a.m. - 1:13 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

7h 58m1 stop Toronto Pearson Intl

2:30 p.m. - 9:57 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

6h 27m1 stop Denver Intl

C$ 1,249Air Canada

Tue, 3 Nov - Thu, 5 Nov

6:00 a.m. - 8:30 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

15h 30m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

6:20 a.m. - 12:19 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

16h 59m1 stop Minneapolis St Paul

C$ 1,403WestJet

Tue, 3 Nov - Thu, 5 Nov

8:35 a.m. - 10:05 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

14h 30m2 stops Calgary Salt Lake City

7:00 a.m. - 8:50 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

12h 50m2 stops New York LaGuardia Toronto Pearson Intl

C$ 1,431WestJet

Tue, 3 Nov - Thu, 5 Nov

6:15 a.m. - 11:57 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

6h 42m1 stop Toronto Pearson Intl

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,450United Airlines

Tue, 3 Nov - Mon, 30 Nov

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 2,172United Airlines

Tue, 3 Nov - Thu, 5 Nov

Cheap direct flights

Enter your travel dates to find the best prices.

3:15 p.m. - 5:00 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,001Air Canada

Mon, 14 Dec - Wed, 16 Dec

8:00 a.m. - 9:31 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 31mdirect

3:35 p.m. - 7:26 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 51mdirect

C$ 1,003Air Canada

Thu, 25 Feb - Sun, 28 Feb

8:00 a.m. - 9:45 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mdirect

3:50 p.m. - 7:28 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 38mdirect

C$ 1,010Air Canada

Tue, 5 Jan - Thu, 7 Jan

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,052Air Canada

Thu, 12 Nov - Tue, 17 Nov

8:00 a.m. - 9:31 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 31mdirect

3:35 p.m. - 7:26 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 51mdirect

C$ 1,105United Airlines

Thu, 25 Feb - Sun, 28 Feb

3:15 p.m. - 5:02 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 47mdirect

10:00 a.m. - 1:52 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 52mdirect

C$ 1,105United Airlines

Sat, 26 Dec - Sun, 27 Dec

8:00 a.m. - 9:45 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mdirect

3:50 p.m. - 7:28 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 38mdirect

C$ 1,105United Airlines

Sun, 7 Feb - Wed, 10 Feb

8:00 a.m. - 9:45 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mdirect

3:50 p.m. - 7:28 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 38mdirect

C$ 1,234Multiple Airlines

Tue, 26 Jan - Fri, 29 Jan

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,262Multiple Airlines

Mon, 23 Nov - Fri, 27 Nov

3:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 1:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,291Multiple Airlines

Mon, 23 Nov - Fri, 27 Nov

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American Airlines flights from Winnipeg to Illinois

Our best American Airlines deals on Winnipeg to Illinois flight tickets

American Airlines

26 Nov

YWG7:00 a.m.Winnipeg

8h 36m

1 stop

ORD2:36 p.m.Chicago O'Hare Intl

3 Dec

ORD2:50 p.m.Chicago O'Hare Intl

7h 07m

1 stop

YWG10:57 p.m.Winnipeg

C$ 758

American Airlines

12 Nov

YWG7:00 a.m.Winnipeg

7h 01m

1 stop

ORD1:01 p.m.Chicago O'Hare Intl

17 Nov

ORD2:50 p.m.Chicago O'Hare Intl

7h 02m

1 stop

YWG10:52 p.m.Winnipeg

C$ 759

American Airlines

23 Nov

YWG7:00 a.m.Winnipeg

7h 10m

1 stop

ORD1:10 p.m.Chicago O'Hare Intl

27 Nov

ORD2:50 p.m.Chicago O'Hare Intl

7h 02m

1 stop

YWG10:52 p.m.Winnipeg

C$ 765

WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets

WestJet

26 Apr

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

ORD4:40 p.m.Chicago O'Hare Intl

3 May

ORD5:30 p.m.Chicago O'Hare Intl

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 649

WestJet

24 Apr

YWG3:45 p.m.Winnipeg

24h 55m

1 stop

ORD4:40 p.m.Chicago O'Hare Intl

2 May

ORD5:30 p.m.Chicago O'Hare Intl

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 743

WestJet

5 Dec

YWG9:35 p.m.Winnipeg

13h 53m

2 stops

MDW10:28 a.m.Chicago Midway

8 Dec

MDW10:24 a.m.Chicago Midway

24h 07m

1 stop

YWG11:31 a.m.Winnipeg

C$ 1,094

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 14/12

7:55 p.m.-11:35 a.m.

1 stop16h 40m

Chicago O'Hare Intl

Wed 16/12

6:20 p.m.-10:15 a.m.

1 stop14h 55m

C$ 555

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 5/1

11:40 a.m.-11:40 a.m.

2 stops25h 00m

Chicago O'Hare Intl

Thu 7/1

6:20 p.m.-10:15 a.m.

1 stop14h 55m

C$ 566

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 1/2

7:00 a.m.-11:50 a.m.

1 stop29h 50m

Chicago O'Hare Intl

Thu 4/2

6:20 p.m.-10:15 a.m.

1 stop14h 55m

C$ 566

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 26/4

7:00 a.m.-4:40 p.m.

1 stop9h 40m

Chicago O'Hare Intl

Mon 3/5

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 649

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 24/4

3:45 p.m.-4:40 p.m.

1 stop24h 55m

Chicago O'Hare Intl

Sun 2/5

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 743

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 26/1

8:15 a.m.-1:13 p.m.

1 stop5h 58m

Chicago O'Hare Intl

Fri 29/1

8:50 p.m.-11:09 a.m.

1 stop13h 19m

C$ 835

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 25/2

9:05 a.m.-2:52 p.m.

1 stop6h 47m

Chicago O'Hare Intl

Sun 28/2

4:30 p.m.-1:24 a.m.

1 stop7h 54m

C$ 934

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 24/4

1:10 p.m.-4:40 p.m.

2 stops27h 30m

Chicago O'Hare Intl

Sun 2/5

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 937

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 25/2

8:00 a.m.-9:31 a.m.

Nonstop2h 31m

Chicago O'Hare Intl

Sun 28/2

3:35 p.m.-7:26 p.m.

Nonstop2h 51m

C$ 1,105

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 26/12

3:15 p.m.-5:02 p.m.

Nonstop2h 47m

Chicago O'Hare Intl

Sun 27/12

10:00 a.m.-1:52 p.m.

Nonstop2h 52m

C$ 1,105

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 Winnipeg to Illinois

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 Illinois?

In general, January is the cheapest month to fly from Winnipeg to Illinois. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 720. If you don’t want to visit Illinois in January, then you should wait until February to fly from Winnipeg, when ticket prices are also cheap, with an average price of C$ 731.

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

According to our data, Saturday is the cheapest day to fly to Illinois from Winnipeg. The lowest ticket price found for a Saturday departure recently was C$ 905. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. The most expensive day to fly to Illinois is Monday, with ticket prices averaging around C$ 1,177.

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

Our most recent data shows that the best time of day to fly to Illinois is in the morning. Flights from Winnipeg to Illinois during this time can be as low as C$ 910. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are C$ 1,284 on average. Flights to Illinois from Winnipeg in the afternoon are generally more expensive because this time of day is more convenient for travellers’ schedules.

What is the cheapest Winnipeg to Illinois flight route?

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

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

There are 4 cabin classes available to choose from on Winnipeg to Illinois 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 Winnipeg to Illinois flights?

You could potentially save up to 31% on your flight if you consider stops on a Winnipeg to Illinois flight.

Cheap Winnipeg to Illinois flight deals and tips

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

Best price found	C$ 296
Fastest flight time	2h 31m
Direct flights	Every day
Airports in Illinois	98 airports

The best one-way flight to Illinois from Winnipeg in the past 72 hours is C$ 296. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is C$ 555.

The fastest flight from Winnipeg to Illinois takes 2h 31m

Direct flights go from Winnipeg to Illinois every day.

There are 98 airports in Illinois. From Winnipeg there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Winnipeg to Illinois

When did momondo last update prices for flights from Winnipeg Airport to Illinois?
Prices for flights from Winnipeg Airport to Illinois are refreshed on a daily basis.
How many operators does momondo search for flights from Winnipeg Airport to Illinois?
As of October 2026, there are 3 operators available to choose from for flights from Winnipeg Airport to Illinois.
How old do you have to be to fly from Winnipeg Airport to Illinois?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Illinois.
What documentation or ID do you need to fly to Illinois?
The travel and health documents you'll need for your trip to Illinois 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 Illinois. 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 Winnipeg to Illinois?
momondo data reveals that the most frequently booked plane model on the route from Winnipeg to Illinois is Embraer 175 (Enhanced Winglets), representing 84.67% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 8.76%, Boeing 737-800 Passenger/BBJ2 (winglets) at 2.19%, and Boeing 737-700 Passenger/BBJ1 (winglets) at 1.46%.

Best airlines flying from Winnipeg to Illinois

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

Airline	Rating	Free Cancellation	Price
WestJet	PriceFrom C$ 274	Free Cancellation	Rating 7.2 3,442 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 694	Free Cancellation	Rating 7.3 10,453 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 712	Free Cancellation	Rating 7.1 11,833 reviews	Search Air Canada flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Illinois from Winnipeg.

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

momondo does allow users to show only those flights to Illinois from Winnipeg which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Illinois from Winnipeg.

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

Yes momondo offers price alerts on flights to Illinois from Winnipeg. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Illinois trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Popular Cities in Illinois

Flights to Fort Lauderdalefrom C$ 186

Flights to Orlandofrom C$ 269

Flights to New Yorkfrom C$ 157

Flights to Los Angelesfrom C$ 224

Flights to Las Vegasfrom C$ 221

Flights to Miamifrom C$ 359

Flights to San Franciscofrom C$ 263

Flights to Honolulufrom C$ 459

Flights to Tampafrom C$ 221

Flights to Houstonfrom C$ 361

Flights to Phoenixfrom C$ 161

Flights to Chicagofrom C$ 287

Cheap flights from Winnipeg to Illinois from C$ 296

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Illinois departing on 11/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Winnipeg to Illinois

Cheap round-trip flights

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Cheap last-minute flights

Cheap direct flights

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

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American Airlines flights from Winnipeg to Illinois

Our best American Airlines deals on Winnipeg to Illinois flight tickets

WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Winnipeg to Illinois that are best for you.

See travel insights to Illinois from

How to get the cheapest flight ticket from Winnipeg to Illinois

What is the cheapest month to fly to Illinois?

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

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

What is the cheapest Winnipeg to Illinois flight route?

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

Can stopping save me money on Winnipeg to Illinois flights?

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

Which airlines fly to Illinois?

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

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

Cheap Winnipeg to Illinois flight deals and tips

Best price found

Fastest flight time

Direct flights

Airports in Illinois

Frequently asked questions about flying from Winnipeg to Illinois

Best airlines flying from Winnipeg to Illinois

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

Why use momondo?

An easier way to manage your Illinois trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Illinois

Popular Cities in Illinois

Popular flights according to clicks in the last 7 days on momondo

Winnipeg flight routes

According to popular flight searches on momondo this year

Illinois flight routes

According to popular flight searches on momondo this year

Fly your favourite airline to Illinois

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According to popular flight searches on momondo this year