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Cheap flights from Winnipeg to Illinois from C$ 169

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 12/1. 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.
Multiple Airlines Logo
9:00 p.m. - 4:52 p.m.
YWG
-
ORD
19h 52m2 stops
Multiple Airlines Logo
2:53 p.m. - 3:07 p.m.
ORD
-
YWG
24h 14m1 stop
C$ 284Multiple Airlines
Tue, 13 Jan - Tue, 20 Jan
Multiple Airlines Logo
12:55 p.m. - 11:47 a.m.
YWG
-
MDW
22h 52m2 stops
Multiple Airlines Logo
12:57 p.m. - 12:43 a.m.
MDW
-
YWG
11h 46m1 stop
C$ 289Multiple Airlines
Wed, 14 Jan - Mon, 19 Jan
WestJet Logo
6:15 a.m. - 1:35 p.m.
YWG
-
ORD
7h 20m1 stop
WestJet Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m1 stop
C$ 295WestJet
Fri, 30 Jan - Fri, 6 Feb
Multiple Airlines Logo
7:30 a.m. - 4:52 p.m.
YWG
-
ORD
9h 22m1 stop
Multiple Airlines Logo
11:48 a.m. - 12:43 a.m.
ORD
-
YWG
12h 55m1 stop
C$ 300Multiple Airlines
Wed, 14 Jan - Mon, 19 Jan
Multiple Airlines Logo
9:00 p.m. - 4:52 p.m.
YWG
-
ORD
19h 52m2 stops
Multiple Airlines Logo
2:53 p.m. - 3:07 p.m.
ORD
-
YWG
24h 14m1 stop
C$ 304Multiple Airlines
Tue, 13 Jan - Tue, 20 Jan
Multiple Airlines Logo
5:05 p.m. - 4:52 p.m.
YWG
-
ORD
23h 47m1 stop
Multiple Airlines Logo
8:41 p.m. - 12:43 a.m.
ORD
-
YWG
28h 02m1 stop
C$ 320Multiple Airlines
Fri, 16 Jan - Sun, 18 Jan
WestJet Logo
12:40 p.m. - 4:43 p.m.
YWG
-
ORD
28h 03m1 stop
WestJet Logo
5:30 p.m. - 5:40 p.m.
ORD
-
YWG
24h 10m1 stop
C$ 322WestJet
Sat, 25 Apr - Thu, 30 Apr
Multiple Airlines Logo
4:10 p.m. - 4:51 p.m.
YWG
-
ORD
24h 41m2 stops
Multiple Airlines Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m1 stop
C$ 327Multiple Airlines
Fri, 30 Jan - Fri, 6 Feb
WestJet Logo
5:00 p.m. - 4:43 p.m.
YWG
-
ORD
23h 43m2 stops
WestJet Logo
5:30 p.m. - 2:30 p.m.
ORD
-
YWG
21h 00m1 stop
C$ 329WestJet
Sat, 25 Apr - Thu, 30 Apr
WestJet Logo
5:00 p.m. - 4:43 p.m.
YWG
-
ORD
23h 43m2 stops
WestJet Logo
5:30 p.m. - 11:00 p.m.
ORD
-
YWG
29h 30m1 stop
C$ 331WestJet
Sat, 25 Apr - Thu, 30 Apr

WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets
WestJet
30 Jan
YWG6:15 a.m.Winnipeg
7h 20m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
6 Feb
ORD2:20 p.m.Chicago O'Hare Intl
8h 20m
1 stop
YWG10:40 p.m.Winnipeg
C$ 295
Find similar
WestJet
25 Apr
YWG12:40 p.m.Winnipeg
28h 03m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
30 Apr
ORD5:30 p.m.Chicago O'Hare Intl
24h 10m
1 stop
YWG5:40 p.m.Winnipeg
C$ 322
Find similar
WestJet
25 Apr
YWG5:00 p.m.Winnipeg
23h 43m
2 stops
ORD4:43 p.m.Chicago O'Hare Intl
30 Apr
ORD5:30 p.m.Chicago O'Hare Intl
21h 00m
1 stop
YWG2:30 p.m.Winnipeg
C$ 329
Find similar

Porter Airlines flights from Winnipeg to Illinois

Our best Porter Airlines deals on Winnipeg to Illinois flight tickets
Porter Airlines
14 Apr
YWG6:00 a.m.Winnipeg
8h 05m
1 stop
ORD2:05 p.m.Chicago O'Hare Intl
18 Apr
ORD8:00 a.m.Chicago O'Hare Intl
7h 30m
1 stop
YWG3:30 p.m.Winnipeg
C$ 575
Find similar
Porter Airlines
14 Apr
YWG6:00 a.m.Winnipeg
8h 05m
1 stop
ORD2:05 p.m.Chicago O'Hare Intl
18 Apr
ORD8:00 a.m.Chicago O'Hare Intl
7h 30m
1 stop
YWG3:30 p.m.Winnipeg
C$ 586
Find similar
Porter Airlines
26 Feb
YWG12:10 p.m.Winnipeg
7h 19m
1 stop
ORD7:29 p.m.Chicago O'Hare Intl
1 Mar
ORD6:40 p.m.Chicago O'Hare Intl
16h 33m
2 stops
YWG11:13 a.m.Winnipeg
C$ 634
Find similar

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 18 December 2025.
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

Tue 13/1

9:00 p.m.-4:52 p.m.

2 stops19h 52m

Chicago O'Hare Intl

Tue 20/1

2:53 p.m.-3:07 p.m.

1 stop24h 14m

C$ 284

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 14/1

12:55 p.m.-11:47 a.m.

2 stops22h 52m

Chicago Midway

Mon 19/1

12:57 p.m.-12:43 a.m.

1 stop11h 46m

C$ 289

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 30/1

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

1 stop7h 20m

Chicago O'Hare Intl

Fri 6/2

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

1 stop8h 20m

C$ 295

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 14/1

7:30 a.m.-4:52 p.m.

1 stop9h 22m

Chicago O'Hare Intl

Mon 19/1

11:48 a.m.-12:43 a.m.

1 stop12h 55m

C$ 300

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 13/1

9:00 p.m.-4:52 p.m.

2 stops19h 52m

Chicago O'Hare Intl

Tue 20/1

2:53 p.m.-3:07 p.m.

1 stop24h 14m

C$ 304

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 16/1

5:05 p.m.-4:52 p.m.

1 stop23h 47m

Chicago O'Hare Intl

Sun 18/1

8:41 p.m.-12:43 a.m.

1 stop28h 02m

C$ 320

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

12:40 p.m.-4:43 p.m.

1 stop28h 03m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-5:40 p.m.

1 stop24h 10m

C$ 322

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 30/1

4:10 p.m.-4:51 p.m.

2 stops24h 41m

Chicago O'Hare Intl

Fri 6/2

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

1 stop8h 20m

C$ 327

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

5:00 p.m.-4:43 p.m.

2 stops23h 43m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-2:30 p.m.

1 stop21h 00m

C$ 329

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

5:00 p.m.-4:43 p.m.

2 stops23h 43m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-11:00 p.m.

1 stop29h 30m

C$ 331

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$ 488. 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$ 493.

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$ 805. 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$ 1,005.

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 afternoon. Flights from Winnipeg to Illinois during this time can be as low as C$ 706. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 894 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 22% 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$ 486

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$ 486. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is C$ 629.
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$ 199Free CancellationRating
7.2
3,204 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 485Free CancellationRating
7.4
9,092 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 495Free CancellationRating
7.1
10,534 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

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Find better results for your trip to Illinois

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