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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 23/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Winnipeg to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
6:15 a.m. - 1:35 p.m.
YWG
-
ORD
7h 20m
1 stop
WestJet Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m
1 stop
C$ 448WestJet
Sun, 25 Oct - Thu, 29 Oct
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 506WestJet
Tue, 29 Sep - Mon, 5 Oct
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m
1 stop
C$ 508WestJet
Thu, 22 Oct - Mon, 26 Oct
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 518WestJet
Thu, 1 Oct - Mon, 5 Oct
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 527WestJet
Tue, 29 Sep - Sun, 4 Oct
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 534WestJet
Mon, 12 Oct - Sun, 18 Oct
Multiple Airlines Logo
5:15 p.m. - 9:40 a.m.
YWG
-
MDW
16h 25m
1 stop
Multiple Airlines Logo
10:25 a.m. - 7:25 p.m.
MDW
-
YWG
9h 00m
1 stop
C$ 577Multiple Airlines
Wed, 1 Jul - Wed, 8 Jul
Delta Logo
6:35 a.m. - 9:45 p.m.
YWG
-
MDW
15h 10m
2 stops
Delta Logo
6:00 a.m. - 11:34 p.m.
MDW
-
YWG
17h 34m
2 stops
C$ 645Delta
Sat, 31 Oct - Wed, 4 Nov
Delta Logo
6:35 a.m. - 9:45 p.m.
YWG
-
MDW
15h 10m
2 stops
Delta Logo
6:00 a.m. - 11:34 p.m.
MDW
-
YWG
17h 34m
2 stops
C$ 661Delta
Sat, 31 Oct - Wed, 4 Nov
Delta Logo
6:35 a.m. - 9:45 p.m.
YWG
-
MDW
15h 10m
2 stops
Delta Logo
6:00 a.m. - 8:16 p.m.
MDW
-
YWG
14h 16m
2 stops
C$ 676Delta
Sat, 31 Oct - Wed, 4 Nov

WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets
WestJet
25 Oct
YWG6:15 a.m.Winnipeg
7h 20m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
29 Oct
ORD2:20 p.m.Chicago O'Hare Intl
8h 20m
1 stop
YWG10:40 p.m.Winnipeg
C$ 448
WestJet
29 Sep
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
5 Oct
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 506
WestJet
22 Oct
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
26 Oct
ORD2:20 p.m.Chicago O'Hare Intl
8h 20m
1 stop
YWG10:40 p.m.Winnipeg
C$ 508

Air Canada flights from Winnipeg to Illinois

Our best Air Canada deals on Winnipeg to Illinois flight tickets
Air Canada
12 Jun
YWG7:20 a.m.Winnipeg
9h 45m
1 stop
ORD5:05 p.m.Chicago O'Hare Intl
15 Jun
ORD9:14 a.m.Chicago O'Hare Intl
2h 38m
YWG11:52 a.m.Winnipeg
C$ 1,022
Air Canada
12 Jun
YWG7:20 a.m.Winnipeg
9h 45m
1 stop
ORD5:05 p.m.Chicago O'Hare Intl
14 Jun
ORD8:00 p.m.Chicago O'Hare Intl
2h 38m
YWG10:38 p.m.Winnipeg
C$ 1,028
Air Canada
12 Jun
YWG7:20 a.m.Winnipeg
9h 45m
1 stop
ORD5:05 p.m.Chicago O'Hare Intl
14 Jun
ORD8:00 p.m.Chicago O'Hare Intl
2h 38m
YWG10:38 p.m.Winnipeg
C$ 1,029

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 6 June 2026.
Use the filters below to find and compare flights from Winnipeg to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 25/10

6:15 a.m.-1:35 p.m.

1 stop7h 20m

Chicago O'Hare Intl

Thu 29/10

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 448

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 29/9

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 5/10

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

1 stop7h 25m

C$ 506

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 22/10

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 26/10

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 508

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 1/10

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

1 stop9h 40m

Chicago O'Hare Intl

Mon 5/10

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

1 stop7h 25m

C$ 518

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 29/9

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$ 527

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 12/10

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

1 stop9h 40m

Chicago O'Hare Intl

Sun 18/10

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

1 stop7h 25m

C$ 534

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 1/7

5:15 p.m.-9:40 a.m.

1 stop16h 25m

Chicago Midway

Wed 8/7

10:25 a.m.-7:25 p.m.

1 stop9h 00m

C$ 577

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 31/10

6:35 a.m.-9:45 p.m.

2 stops15h 10m

Chicago Midway

Wed 4/11

6:00 a.m.-11:34 p.m.

2 stops17h 34m

C$ 645

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 31/10

6:35 a.m.-9:45 p.m.

2 stops15h 10m

Chicago Midway

Wed 4/11

6:00 a.m.-11:34 p.m.

2 stops17h 34m

C$ 661

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 31/10

6:35 a.m.-9:45 p.m.

2 stops15h 10m

Chicago Midway

Wed 4/11

6:00 a.m.-8:16 p.m.

2 stops14h 16m

C$ 676

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Illinois from

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

What is the cheapest month to fly to Illinois?

In general, October 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$ 111. If you don’t want to visit Illinois in October, then you should wait until November to fly from Winnipeg, when ticket prices are also cheap, with an average price of C$ 177.

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

According to our data, Friday is the cheapest day to fly to Illinois from Winnipeg. The lowest ticket price found for a Friday departure recently was C$ 838. 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$ 1,156.

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$ 851. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 991 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 42% 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$ 275

Fastest flight time

2h 21m

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$ 275. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is C$ 844.
The fastest flight from Winnipeg to Illinois takes 2h 21m
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?

  • 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?

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
WestJetPriceFrom C$ 272Free CancellationRating
7.2
3,351 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 367Free CancellationRating
7.1
11,131 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 490Free CancellationRating
7.4
9,775 reviews
Search United Airlines 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

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Find better results for your trip to Illinois

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