Which airlines fly to Illinois?

United Airlines, WestJet and Air Canada 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 35% 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.

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

The number of flights available between Winnipeg and Illinois is 52 per week as of September 2026. The most frequent departure day is Mon, with 15% of weekly flights leaving on this day.

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 day?

7 flights are operational daily from Winnipeg to Illinois as of September 2026. The most popular departure time for this route is 2:00p.m., with 51% of flights per day taking off in the afternoon.

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 September 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$ 240 Cheap Flights from Winnipeg to Illinois in 2026

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.

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

9h 40m1 stop Calgary

5:30 p.m. - 5:25 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

23h 55m1 stop Calgary

C$ 447WestJet

Sun, 27 Sep - Fri, 2 Oct

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

9h 40m1 stop Calgary

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

23h 50m2 stops Toronto Island Ottawa

C$ 479Multiple Airlines

Fri, 23 Oct - Mon, 26 Oct

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

9h 40m1 stop Calgary

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

23h 50m2 stops Toronto Island Ottawa

C$ 479Multiple Airlines

Thu, 22 Oct - Mon, 26 Oct

4:55 p.m. - 4:40 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

23h 45m1 stop Calgary

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

7h 25m1 stop Calgary

C$ 485WestJet

Wed, 21 Oct - Fri, 23 Oct

4:15 p.m. - 11:40 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

19h 25m2 stops Ottawa Toronto Pearson Intl

6:20 p.m. - 9:15 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

14h 55m1 stop Toronto Island

C$ 485Multiple Airlines

Sat, 24 Oct - Sun, 25 Oct

5:00 a.m. - 1:23 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

8h 23m1 stop Toronto Pearson Intl

9:55 a.m. - 6:12 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 17m1 stop Toronto Pearson Intl

C$ 664Air Canada

Tue, 13 Oct - Thu, 15 Oct

5:00 a.m. - 1:23 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

8h 23m1 stop Toronto Pearson Intl

9:55 a.m. - 6:12 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

8h 17m1 stop Toronto Pearson Intl

C$ 666Air Canada

Sun, 18 Oct - Tue, 20 Oct

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$ 724WestJet

Thu, 1 Oct - Sun, 4 Oct

7:15 a.m. - 8:00 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

24h 45m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

7:00 a.m. - 11:44 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

16h 44m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

C$ 949United Airlines

Sun, 15 Nov - Tue, 15 Dec

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:29 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 54mdirect

C$ 1,026United Airlines

Fri, 23 Oct - Mon, 26 Oct

Cheap last-minute flights

Enter your travel dates to find the best prices.

8:10 p.m. - 2:35 p.m.YWG Winnipeg-MDW Chicago Midway

18h 25m1 stop Toronto Pearson Intl

3:20 p.m. - 9:45 a.m.MDW Chicago Midway-YWG Winnipeg

18h 25m1 stop Toronto Island

C$ 890Multiple Airlines

Fri, 18 Sep - Sun, 20 Sep

8:10 p.m. - 11:00 a.m.YWG Winnipeg-MDW Chicago Midway

14h 50m1 stop Toronto Pearson Intl

3:20 p.m. - 10:43 a.m.MDW Chicago Midway-YWG Winnipeg

19h 23m2 stops Toronto Island Ottawa

C$ 913Multiple Airlines

Fri, 18 Sep - Sun, 20 Sep

5:10 p.m. - 11:00 a.m.YWG Winnipeg-MDW Chicago Midway

17h 50m1 stop Toronto Pearson Intl

3:20 p.m. - 8:40 a.m.MDW Chicago Midway-YWG Winnipeg

17h 20m1 stop Toronto Island

C$ 964Multiple Airlines

Thu, 17 Sep - Sat, 19 Sep

9:05 p.m. - 5:51 p.m.YWG Winnipeg-MDW Chicago Midway

20h 46m2 stops Calgary Atlanta Hartsfield-Jackson

3:20 p.m. - 8:40 a.m.MDW Chicago Midway-YWG Winnipeg

17h 20m1 stop Toronto Island

C$ 1,046Multiple Airlines

Thu, 17 Sep - Sat, 19 Sep

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:15 a.m. - 11:52 a.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

C$ 1,151Air Canada

Fri, 18 Sep - Sun, 20 Sep

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

8:45 a.m. - 3:09 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

6h 24m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 1,162Air Canada

Fri, 18 Sep - Sun, 20 Sep

9:05 p.m. - 2:29 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

17h 24m2 stops Calgary Atlanta Hartsfield-Jackson

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

7h 25m1 stop Calgary

C$ 1,333WestJet

Thu, 17 Sep - Mon, 21 Sep

7:10 p.m. - 4:37 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

21h 27m2 stops Calgary Atlanta Hartsfield-Jackson

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

7h 25m1 stop Calgary

C$ 1,344WestJet

Mon, 14 Sep - Fri, 18 Sep

7:00 a.m. - 8:30 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

13h 30m2 stops Calgary Detroit Metropolitan Wayne County

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

7h 25m1 stop Calgary

C$ 1,355WestJet

Thu, 17 Sep - Mon, 21 Sep

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:45 a.m. - 4:27 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

6h 42m1 stop Toronto Pearson Intl

C$ 1,405Air Canada

Thu, 17 Sep - Sat, 19 Sep

Cheap direct flights

Enter your travel dates to find the best prices.

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:29 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 54mdirect

C$ 921Air Canada

Thu, 22 Oct - Sun, 25 Oct

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

7:54 p.m. - 10:33 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mdirect

C$ 921Air Canada

Fri, 9 Oct - Sun, 11 Oct

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

7:54 p.m. - 10:33 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 39mdirect

C$ 921Air Canada

Thu, 8 Oct - Sat, 10 Oct

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:29 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 54mdirect

C$ 922Air Canada

Fri, 23 Oct - Fri, 30 Oct

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:29 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 54mdirect

C$ 1,026United Airlines

Fri, 23 Oct - Mon, 26 Oct

2:00 p.m. - 4:35 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:29 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 54mdirect

C$ 1,026United Airlines

Thu, 22 Oct - Mon, 26 Oct

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:29 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 54mdirect

C$ 1,026United Airlines

Wed, 21 Oct - Mon, 26 Oct

7:00 a.m. - 9:35 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

10:00 a.m. - 12:37 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mdirect

C$ 1,129Multiple Airlines

Sun, 18 Oct - Tue, 20 Oct

7:00 a.m. - 9:45 a.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 45mdirect

7:45 p.m. - 10:33 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,132Multiple Airlines

Thu, 14 Jan - Sat, 30 Jan

2:15 p.m. - 4:50 p.m.YWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mdirect

9:35 a.m. - 12:23 p.m.ORD Chicago O'Hare Intl-YWG Winnipeg

2h 48mdirect

C$ 1,153Multiple Airlines

Thu, 26 Nov - Mon, 30 Nov

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Porter Airlines flights from Winnipeg to Illinois

Our best Porter Airlines deals on Winnipeg to Illinois flight tickets

Porter Airlines

24 Oct

YWG9:20 a.m.Winnipeg

26h 20m

1 stop

ORD11:40 a.m.Chicago O'Hare Intl

25 Oct

ORD6:20 p.m.Chicago O'Hare Intl

16h 25m

1 stop

YWG10:45 a.m.Winnipeg

C$ 505

Porter Airlines

19 Nov

YWG7:00 a.m.Winnipeg

7h 36m

1 stop

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

23 Nov

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

7h 07m

1 stop

YWG9:57 p.m.Winnipeg

C$ 671

Porter Airlines

14 Nov

YWG7:00 a.m.Winnipeg

7h 37m

1 stop

ORD2:37 p.m.Chicago O'Hare Intl

14 Dec

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

7h 07m

1 stop

YWG9:57 p.m.Winnipeg

C$ 674

WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets

WestJet

18 Oct

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

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

19 Oct

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

17h 40m

1 stop

YWG11:10 a.m.Winnipeg

C$ 469

WestJet

21 Oct

YWG4:55 p.m.Winnipeg

23h 45m

1 stop

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

23 Oct

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

7h 25m

1 stop

YWG12:55 a.m.Winnipeg

C$ 485

WestJet

18 Oct

YWG7:00 a.m.Winnipeg

9h 40m

1 stop

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

19 Oct

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

16h 05m

2 stops

YWG9:35 a.m.Winnipeg

C$ 508

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 27/9

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

1 stop9h 40m

Chicago O'Hare Intl

Fri 2/10

5:30 p.m.-5:25 p.m.

1 stop23h 55m

C$ 447

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 23/10

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 26/10

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

2 stops23h 50m

C$ 479

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 22/10

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 26/10

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

2 stops23h 50m

C$ 479

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 21/10

4:55 p.m.-4:40 p.m.

1 stop23h 45m

Chicago O'Hare Intl

Fri 23/10

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

1 stop7h 25m

C$ 485

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 24/10

4:15 p.m.-11:40 a.m.

2 stops19h 25m

Chicago O'Hare Intl

Sun 25/10

6:20 p.m.-9:15 a.m.

1 stop14h 55m

C$ 485

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 13/10

5:00 a.m.-1:23 p.m.

1 stop8h 23m

Chicago O'Hare Intl

Thu 15/10

9:55 a.m.-6:12 p.m.

1 stop8h 17m

C$ 664

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 18/10

5:00 a.m.-1:23 p.m.

1 stop8h 23m

Chicago O'Hare Intl

Tue 20/10

9:55 a.m.-6:12 p.m.

1 stop8h 17m

C$ 666

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 1/10

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

1 stop9h 40m

Chicago O'Hare Intl

Sun 4/10

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

1 stop7h 25m

C$ 724

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 15/11

7:15 a.m.-8:00 a.m.

2 stops24h 45m

Chicago O'Hare Intl

Tue 15/12

7:00 a.m.-11:44 p.m.

2 stops16h 44m

C$ 949

Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 23/10

2:00 p.m.-4:35 p.m.

Nonstop2h 35m

Chicago O'Hare Intl

Mon 26/10

9:29 a.m.-12:23 p.m.

Nonstop2h 54m

C$ 1,026

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, November 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$ 675. If you don’t want to visit Illinois in November, then you should wait until February to fly from Winnipeg, when ticket prices are also cheap, with an average price of C$ 714.

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

According to our data, Wednesday is the cheapest day to fly to Illinois from Winnipeg. The lowest ticket price found for a Wednesday departure recently was C$ 824. 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$ 1,145.

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$ 886. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 979 on average. Flights to Illinois from Winnipeg at noon 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 38% 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$ 240
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$ 240. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is C$ 447.

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 September 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 86.67% of all bookings. The subsequent popular models are Boeing 737-700 Passenger/BBJ1 (winglets) at 5.93%, Boeing 737 MAX 8 at 2.96%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 1.48%.

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$ 271	Free Cancellation	Rating 7.2 3,444 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 688	Free Cancellation	Rating 7.4 10,211 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 706	Free Cancellation	Rating 7.1 11,619 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$ 216

Flights to Orlandofrom C$ 237

Flights to New Yorkfrom C$ 301

Flights to Los Angelesfrom C$ 226

Flights to Las Vegasfrom C$ 237

Flights to Miamifrom C$ 379

Flights to San Franciscofrom C$ 284

Flights to Honolulufrom C$ 362

Flights to Houstonfrom C$ 333

Flights to Phoenixfrom C$ 204

Flights to Chicagofrom C$ 259

Flights to Tampafrom C$ 209

Cheap flights from Winnipeg to Illinois from C$ 240

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 18/10. 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

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Cheap last-minute flights

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Big names, great deals

Big names, great deals

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Filter for what you want

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Porter Airlines flights from Winnipeg to Illinois

Our best Porter 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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