Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to Illinois from C$ 173

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 31/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Winnipeg to Illinois

Cheap round-trip flights

WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
5:30 p.m. - 9:01 a.m.ORD-YWG
15h 31m1 stop
C$ 268WestJet
Find Deal
Sun, 12 Oct - Sun, 19 Oct
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
5:30 p.m. - 9:01 a.m.ORD-YWG
15h 31m1 stop
C$ 281WestJet
Find Deal
Fri, 17 Oct - Sun, 19 Oct
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
5:30 p.m. - 11:26 a.m.ORD-YWG
17h 56m2 stops
C$ 299WestJet
Find Deal
Fri, 17 Oct - Sun, 19 Oct
Multiple Airlines Logo
9:00 p.m. - 6:39 p.m.YWG-MDW
21h 39m2 stops
Multiple Airlines Logo
1:37 p.m. - 3:07 p.m.MDW-YWG
25h 30m1 stop
C$ 300Multiple Airlines
Find Deal
Thu, 30 Oct - Thu, 6 Nov
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
C$ 300WestJet
Find Deal
Fri, 3 Oct - Sat, 4 Oct
Multiple Airlines Logo
7:30 a.m. - 6:39 p.m.YWG-MDW
11h 09m1 stop
Multiple Airlines Logo
5:20 a.m. - 2:07 p.m.MDW-YWG
8h 47m1 stop
C$ 318Multiple Airlines
Find Deal
Fri, 31 Oct - Sun, 2 Nov
United Airlines Logo
7:00 a.m. - 9:31 a.m.YWG-ORD
2h 31mdirect
United Airlines Logo
5:01 a.m. - 1:09 p.m.ORD-YWG
8h 08m1 stop
C$ 469United Airlines
Find Deal
Thu, 16 Oct - Sun, 19 Oct
United Airlines Logo
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
United Airlines Logo
1:01 p.m. - 3:31 p.m.ORD-YWG
2h 30mdirect
C$ 470United Airlines
Find Deal
Thu, 9 Oct - Sun, 12 Oct
Delta Logo
6:40 a.m. - 1:08 p.m.YWG-MDW
6h 28m1 stop
Delta Logo
9:20 a.m. - 4:50 p.m.MDW-YWG
7h 30m1 stop
C$ 615Delta
Find Deal
Thu, 9 Oct - Sun, 12 Oct
Delta Logo
12:40 p.m. - 6:08 p.m.YWG-MDW
5h 28m1 stop
Delta Logo
6:00 a.m. - 3:09 p.m.MDW-YWG
9h 09m1 stop
C$ 761Delta
Find Deal
Tue, 3 Mar - Sun, 8 Mar

WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets
WestJet
12 Oct
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
19 Oct
ORD5:30 p.m.Chicago O'Hare Intl
15h 31m
1 stop
YWG9:01 a.m.Winnipeg
C$ 268
Find similar
WestJet
17 Oct
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
19 Oct
ORD5:30 p.m.Chicago O'Hare Intl
15h 31m
1 stop
YWG9:01 a.m.Winnipeg
C$ 281
Find similar
WestJet
17 Oct
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
19 Oct
ORD5:30 p.m.Chicago O'Hare Intl
17h 56m
2 stops
YWG11:26 a.m.Winnipeg
C$ 299
Find similar

United Airlines flights from Winnipeg to Illinois

Our best United Airlines deals on Winnipeg to Illinois flight tickets
United Airlines
16 Oct
YWG7:00 a.m.Winnipeg
2h 31m
ORD9:31 a.m.Chicago O'Hare Intl
19 Oct
ORD5:01 a.m.Chicago O'Hare Intl
8h 08m
1 stop
YWG1:09 p.m.Winnipeg
C$ 469
Find similar
United Airlines
9 Oct
YWG2:20 p.m.Winnipeg
2h 31m
ORD4:51 p.m.Chicago O'Hare Intl
12 Oct
ORD1:01 p.m.Chicago O'Hare Intl
2h 30m
YWG3:31 p.m.Winnipeg
C$ 470
Find similar
United Airlines
9 Oct
YWG2:20 p.m.Winnipeg
2h 31m
ORD4:51 p.m.Chicago O'Hare Intl
12 Oct
ORD5:01 a.m.Chicago O'Hare Intl
8h 08m
1 stop
YWG1:09 p.m.Winnipeg
C$ 472
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 17 September 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

Sun 12/10

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Sun 19/10

5:30 p.m.-9:01 a.m.

1 stop15h 31m

C$ 268

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 17/10

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Sun 19/10

5:30 p.m.-9:01 a.m.

1 stop15h 31m

C$ 281

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 17/10

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Sun 19/10

5:30 p.m.-11:26 a.m.

2 stops17h 56m

C$ 299

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 30/10

9:00 p.m.-6:39 p.m.

2 stops21h 39m

Chicago Midway

Thu 6/11

1:37 p.m.-3:07 p.m.

1 stop25h 30m

C$ 300

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 3/10

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Sat 4/10

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 300

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 31/10

7:30 a.m.-6:39 p.m.

1 stop11h 09m

Chicago Midway

Sun 2/11

5:20 a.m.-2:07 p.m.

1 stop8h 47m

C$ 318

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 16/10

7:00 a.m.-9:31 a.m.

Nonstop2h 31m

Chicago O'Hare Intl

Sun 19/10

5:01 a.m.-1:09 p.m.

1 stop8h 08m

C$ 469

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/10

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

Chicago O'Hare Intl

Sun 12/10

1:01 p.m.-3:31 p.m.

Nonstop2h 30m

C$ 470

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 9/10

6:40 a.m.-1:08 p.m.

1 stop6h 28m

Chicago Midway

Sun 12/10

9:20 a.m.-4:50 p.m.

1 stop7h 30m

C$ 615

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

12:40 p.m.-6:08 p.m.

1 stop5h 28m

Chicago Midway

Sun 8/3

6:00 a.m.-3:09 p.m.

1 stop9h 09m

C$ 761

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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$ 499. 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$ 549.

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$ 798. 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$ 967.

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$ 705. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 863 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 58% 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$ 583

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Illinois

1 airport
The best one-way flight to Illinois from Winnipeg in the past 72 hours is C$ 583. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is C$ 545.
The fastest flight from Winnipeg to Illinois takes 2h 21m
Direct flights go from Winnipeg to Illinois every day.
There is 1 airport near Illinois: 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
3,095 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 321Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 484Free CancellationRating
7.4
8,926 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

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 17/10
Fri 24/10
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Illinois

Popular Cities in Illinois

Popular flights according to clicks in the last 7 days on momondo
Flights to Fort Lauderdalefrom C$ 143
Flights to Orlandofrom C$ 155
Flights to New Yorkfrom C$ 249
Flights to Las Vegasfrom C$ 144
Flights to Los Angelesfrom C$ 151
Flights to Miamifrom C$ 268
Flights to San Franciscofrom C$ 133
Flights to Honolulufrom C$ 254
Flights to Phoenixfrom C$ 191
Flights to Tampafrom C$ 221
Flights to Chicagofrom C$ 223
Flights to Houstonfrom C$ 234