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Cheap flights from Winnipeg to Illinois from C$ 249

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 23/4. 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

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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
9:00 p.m. - 4:40 p.m.
YWG
-
ORD
19h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 399WestJet
Sat, 25 Apr - Thu, 30 Apr
WestJet Logo
6:55 p.m. - 4:40 p.m.
YWG
-
ORD
21h 45m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 400WestJet
Sat, 25 Apr - Thu, 30 Apr
WestJet Logo
7:50 a.m. - 1:35 p.m.
YWG
-
ORD
29h 45m
1 stop
WestJet Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m
1 stop
C$ 402WestJet
Thu, 5 Mar - Mon, 9 Mar
WestJet Logo
7:50 a.m. - 1:35 p.m.
YWG
-
ORD
29h 45m
1 stop
WestJet Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m
1 stop
C$ 403WestJet
Thu, 5 Mar - Mon, 9 Mar
WestJet Logo
5:00 p.m. - 4:40 p.m.
YWG
-
ORD
23h 40m
2 stops
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 407WestJet
Sat, 25 Apr - Thu, 30 Apr
WestJet Logo
5:00 p.m. - 4:40 p.m.
YWG
-
ORD
23h 40m
2 stops
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 408WestJet
Sat, 25 Apr - Thu, 30 Apr
WestJet Logo
5:00 p.m. - 4:40 p.m.
YWG
-
ORD
23h 40m
2 stops
WestJet Logo
5:30 p.m. - 9:35 a.m.
ORD
-
YWG
16h 05m
2 stops
C$ 456WestJet
Sat, 25 Apr - Thu, 30 Apr
WestJet Logo
5:00 p.m. - 4:40 p.m.
YWG
-
ORD
23h 40m
2 stops
WestJet Logo
5:30 p.m. - 9:35 a.m.
ORD
-
YWG
16h 05m
2 stops
C$ 463WestJet
Sat, 25 Apr - Thu, 30 Apr
Multiple Airlines Logo
12:20 p.m. - 3:52 p.m.
YWG
-
ORD
27h 32m
2 stops
Multiple Airlines Logo
7:41 p.m. - 3:09 p.m.
ORD
-
YWG
19h 28m
1 stop
C$ 466Multiple Airlines
Tue, 3 Mar - Tue, 10 Mar
Multiple Airlines Logo
8:20 p.m. - 10:05 a.m.
YWG
-
MDW
13h 45m
1 stop
Multiple Airlines Logo
9:51 p.m. - 7:35 p.m.
MDW
-
YWG
21h 44m
2 stops
C$ 500Multiple Airlines
Thu, 5 Mar - Mon, 9 Mar

WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets
WestJet
25 Apr
YWG9:00 p.m.Winnipeg
19h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
30 Apr
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 399
WestJet
25 Apr
YWG6:55 p.m.Winnipeg
21h 45m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
30 Apr
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
C$ 400
WestJet
5 Mar
YWG7:50 a.m.Winnipeg
29h 45m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
9 Mar
ORD2:20 p.m.Chicago O'Hare Intl
8h 20m
1 stop
YWG10:40 p.m.Winnipeg
C$ 402

United Airlines flights from Winnipeg to Illinois

Our best United Airlines deals on Winnipeg to Illinois flight tickets
United Airlines
25 Apr
YWG2:00 p.m.Winnipeg
2h 35m
ORD4:35 p.m.Chicago O'Hare Intl
30 Apr
ORD9:18 a.m.Chicago O'Hare Intl
2h 34m
YWG11:52 a.m.Winnipeg
C$ 769
United Airlines
3 Mar
YWG2:20 p.m.Winnipeg
2h 25m
ORD4:45 p.m.Chicago O'Hare Intl
10 Mar
ORD9:15 a.m.Chicago O'Hare Intl
2h 42m
YWG11:57 a.m.Winnipeg
C$ 770
United Airlines
7 Feb
YWG2:20 p.m.Winnipeg
2h 43m
ORD5:03 p.m.Chicago O'Hare Intl
14 Feb
ORD2:00 p.m.Chicago O'Hare Intl
5h 34m
1 stop
YWG7:34 p.m.Winnipeg
C$ 1,216

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 4 February 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

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

9:00 p.m.-4:40 p.m.

1 stop19h 40m

Chicago O'Hare Intl

Thu 30/4

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

1 stop7h 25m

C$ 399

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

6:55 p.m.-4:40 p.m.

1 stop21h 45m

Chicago O'Hare Intl

Thu 30/4

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

1 stop7h 25m

C$ 400

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 5/3

7:50 a.m.-1:35 p.m.

1 stop29h 45m

Chicago O'Hare Intl

Mon 9/3

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

1 stop8h 20m

C$ 402

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 5/3

7:50 a.m.-1:35 p.m.

1 stop29h 45m

Chicago O'Hare Intl

Mon 9/3

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

1 stop8h 20m

C$ 403

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

5:00 p.m.-4:40 p.m.

2 stops23h 40m

Chicago O'Hare Intl

Thu 30/4

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

1 stop7h 25m

C$ 407

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

5:00 p.m.-4:40 p.m.

2 stops23h 40m

Chicago O'Hare Intl

Thu 30/4

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

1 stop7h 25m

C$ 408

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

5:00 p.m.-4:40 p.m.

2 stops23h 40m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-9:35 a.m.

2 stops16h 05m

C$ 456

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

5:00 p.m.-4:40 p.m.

2 stops23h 40m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-9:35 a.m.

2 stops16h 05m

C$ 463

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 3/3

12:20 p.m.-3:52 p.m.

2 stops27h 32m

Chicago O'Hare Intl

Tue 10/3

7:41 p.m.-3:09 p.m.

1 stop19h 28m

C$ 466

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 5/3

8:20 p.m.-10:05 a.m.

1 stop13h 45m

Chicago Midway

Mon 9/3

9:51 p.m.-7:35 p.m.

2 stops21h 44m

C$ 500

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$ 484. 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$ 489.

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$ 765. 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 Sunday, with ticket prices averaging around C$ 1,014.

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$ 834. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 917 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 64% 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$ 259

Fastest flight time

2h 21m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun

Airports in Illinois

98 airports
The best one-way flight to Illinois from Winnipeg in the past 72 hours is C$ 259. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is C$ 568.
The fastest flight from Winnipeg to Illinois takes 2h 21m
Direct flights go from Winnipeg to Illinois on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 98 airports in Illinois. From Winnipeg there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • 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$ 198Free CancellationRating
7.2
3,255 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 357Free CancellationRating
7.1
10,688 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 481Free CancellationRating
7.4
9,236 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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