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Cheap flights from Winnipeg to Illinois from C$ 267

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 7/9. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
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$ 382WestJet
Fri, 2 Oct - 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$ 388WestJet
Thu, 15 Oct - Sun, 18 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$ 395WestJet
Thu, 15 Oct - Fri, 16 Oct
Multiple Airlines Logo
6:15 a.m. - 8:12 p.m.
YWG
-
ORD
13h 57m
2 stops
Multiple Airlines Logo
3:40 p.m. - 9:45 a.m.
ORD
-
YWG
18h 05m
2 stops
C$ 471Multiple Airlines
Wed, 9 Sep - Wed, 16 Sep
Multiple Airlines Logo
11:15 a.m. - 11:00 a.m.
YWG
-
MDW
23h 45m
2 stops
Multiple Airlines Logo
11:45 a.m. - 8:45 p.m.
MDW
-
YWG
9h 00m
1 stop
C$ 474Multiple Airlines
Thu, 17 Sep - Mon, 21 Sep
Multiple Airlines Logo
11:15 a.m. - 11:00 a.m.
YWG
-
MDW
23h 45m
2 stops
Multiple Airlines Logo
11:45 a.m. - 8:45 p.m.
MDW
-
YWG
9h 00m
1 stop
C$ 474Multiple Airlines
Mon, 14 Sep - Mon, 21 Sep
Air Canada Logo
2:05 p.m. - 7:48 p.m.
YWG
-
ORD
5h 43m
1 stop
Air Canada Logo
2:15 p.m. - 9:27 p.m.
ORD
-
YWG
7h 12m
1 stop
C$ 690Air Canada
Thu, 10 Sep - Wed, 16 Sep
Air Canada Logo
2:05 p.m. - 7:48 p.m.
YWG
-
ORD
5h 43m
1 stop
Air Canada Logo
2:15 p.m. - 9:27 p.m.
ORD
-
YWG
7h 12m
1 stop
C$ 690Air Canada
Tue, 15 Sep - Wed, 23 Sep
United Airlines Logo
2:00 p.m. - 4:35 p.m.
YWG
-
ORD
2h 35mdirect
United Airlines Logo
7:54 p.m. - 10:33 p.m.
ORD
-
YWG
2h 39mdirect
C$ 951United Airlines
Thu, 10 Sep - Thu, 17 Sep
United Airlines Logo
2:00 p.m. - 4:35 p.m.
YWG
-
ORD
2h 35mdirect
United Airlines Logo
10:00 a.m. - 12:37 p.m.
ORD
-
YWG
2h 37mdirect
C$ 951United Airlines
Wed, 23 Sep - Sat, 26 Sep

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WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets
WestJet
2 Oct
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
4 Oct
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 382
WestJet
15 Oct
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
18 Oct
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 388
WestJet
15 Oct
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
16 Oct
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 395

Porter Airlines flights from Winnipeg to Illinois

Our best Porter Airlines deals on Winnipeg to Illinois flight tickets
Porter Airlines
7 Oct
YWG9:20 a.m.Winnipeg
6h 59m
1 stop
ORD4:19 p.m.Chicago O'Hare Intl
14 Oct
ORD8:06 a.m.Chicago O'Hare Intl
7h 13m
1 stop
YWG3:19 p.m.Winnipeg
C$ 635
Porter Airlines
2 Sep
YWG9:20 a.m.Winnipeg
6h 59m
1 stop
ORD4:19 p.m.Chicago O'Hare Intl
9 Sep
ORD9:45 a.m.Chicago O'Hare Intl
10h 09m
1 stop
YWG7:54 p.m.Winnipeg
C$ 643
Porter Airlines
11 Sep
YWG4:15 p.m.Winnipeg
22h 20m
2 stops
MDW2:35 p.m.Chicago Midway
18 Sep
MDW3:20 p.m.Chicago Midway
26h 38m
2 stops
YWG5:58 p.m.Winnipeg
C$ 751

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 29 July 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

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 2/10

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$ 382

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 15/10

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$ 388

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 15/10

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

1 stop9h 40m

Chicago O'Hare Intl

Fri 16/10

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

1 stop7h 25m

C$ 395

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 9/9

6:15 a.m.-8:12 p.m.

2 stops13h 57m

Chicago O'Hare Intl

Wed 16/9

3:40 p.m.-9:45 a.m.

2 stops18h 05m

C$ 471

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 17/9

11:15 a.m.-11:00 a.m.

2 stops23h 45m

Chicago Midway

Mon 21/9

11:45 a.m.-8:45 p.m.

1 stop9h 00m

C$ 474

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 14/9

11:15 a.m.-11:00 a.m.

2 stops23h 45m

Chicago Midway

Mon 21/9

11:45 a.m.-8:45 p.m.

1 stop9h 00m

C$ 474

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/9

2:05 p.m.-7:48 p.m.

1 stop5h 43m

Chicago O'Hare Intl

Wed 16/9

2:15 p.m.-9:27 p.m.

1 stop7h 12m

C$ 690

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 15/9

2:05 p.m.-7:48 p.m.

1 stop5h 43m

Chicago O'Hare Intl

Wed 23/9

2:15 p.m.-9:27 p.m.

1 stop7h 12m

C$ 690

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/9

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

Nonstop2h 35m

Chicago O'Hare Intl

Thu 17/9

7:54 p.m.-10:33 p.m.

Nonstop2h 39m

C$ 951
Quickest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 23/9

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

Nonstop2h 35m

Chicago O'Hare Intl

Sat 26/9

10:00 a.m.-12:37 p.m.

Nonstop2h 37m

C$ 951

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, September 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$ 535. If you don’t want to visit Illinois in September, then you should wait until October to fly from Winnipeg, when ticket prices are also cheap, with an average price of C$ 546.

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$ 829. 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$ 1,166.

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$ 859. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 992 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 21% 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$ 737

Fastest flight time

2h 34m

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$ 737. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is C$ 677.
The fastest flight from Winnipeg to Illinois takes 2h 34m
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$ 276Free CancellationRating
7.2
3,415 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 372Free CancellationRating
7.1
11,404 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 496Free CancellationRating
7.4
10,050 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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