Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Illinois to Winnipeg from C$ 119

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Winnipeg departing on 18/10. 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 Illinois to Winnipeg

Cheap round-trip flights

WestJet Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
WestJet Logo
6:15 a.m. - 1:35 p.m.YWG-ORD
7h 20m1 stop
C$ 216WestJet
Find Deal
Sat, 18 Oct - Sun, 26 Oct
WestJet Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
WestJet Logo
6:15 a.m. - 1:35 p.m.YWG-ORD
7h 20m1 stop
C$ 217WestJet
Find Deal
Sat, 18 Oct - Sun, 26 Oct
Logo
6:00 a.m. - 12:30 a.m.ORD-YWG
18h 30m2 stops
Logo
6:15 a.m. - 1:35 p.m.YWG-ORD
7h 20m1 stop
C$ 272
Find Deal
Sat, 18 Oct - Sun, 26 Oct
Logo
5:45 p.m. - 12:30 a.m.ORD-YWG
30h 45m2 stops
Logo
6:15 a.m. - 1:35 p.m.YWG-ORD
7h 20m1 stop
C$ 274
Find Deal
Sat, 18 Oct - Sun, 26 Oct
Delta Logo
7:10 p.m. - 11:27 p.m.MDW-YWG
4h 17m1 stop
Delta Logo
8:00 a.m. - 1:08 p.m.YWG-MDW
5h 08m1 stop
C$ 770Delta
Find Deal
Sat, 18 Oct - Sun, 26 Oct
Delta Logo
8:53 a.m. - 4:50 p.m.STL-YWG
7h 57m1 stop
Delta Logo
6:40 a.m. - 5:29 p.m.YWG-STL
10h 49m2 stops
C$ 779Delta
Find Deal
Sat, 11 Oct - Wed, 15 Oct
United Airlines Logo
11:30 a.m. - 10:33 p.m.STL-YWG
11h 03m1 stop
United Airlines Logo
7:00 a.m. - 10:35 p.m.YWG-STL
15h 35m1 stop
C$ 887United Airlines
Find Deal
Tue, 23 Sep - Wed, 1 Oct
United Airlines Logo
12:25 p.m. - 10:33 p.m.STL-YWG
10h 08m1 stop
United Airlines Logo
4:25 p.m. - 10:49 a.m.YWG-STL
18h 24m2 stops
C$ 901United Airlines
Find Deal
Wed, 1 Oct - Mon, 6 Oct
Air Canada Logo
4:05 p.m. - 11:44 p.m.STL-YWG
7h 39m1 stop
Air Canada Logo
7:15 a.m. - 3:29 p.m.YWG-STL
8h 14m1 stop
C$ 927Air Canada
Find Deal
Tue, 3 Mar - Wed, 4 Mar
Air Canada Logo
10:30 a.m. - 8:28 p.m.STL-YWG
9h 58m2 stops
Air Canada Logo
7:15 a.m. - 3:29 p.m.YWG-STL
8h 14m1 stop
C$ 1,036Air Canada
Find Deal
Tue, 3 Mar - Wed, 4 Mar

United Airlines flights from Illinois to Winnipeg

Our best United Airlines deals on Illinois to Winnipeg flight tickets
United Airlines
23 Sep
STL11:30 a.m.Lambert-St Louis
11h 03m
1 stop
YWG10:33 p.m.Winnipeg
1 Oct
YWG7:00 a.m.Winnipeg
15h 35m
1 stop
STL10:35 p.m.Lambert-St Louis
C$ 887
Find similar
United Airlines
1 Oct
STL12:25 p.m.Lambert-St Louis
10h 08m
1 stop
YWG10:33 p.m.Winnipeg
6 Oct
YWG4:25 p.m.Winnipeg
18h 24m
2 stops
STL10:49 a.m.Lambert-St Louis
C$ 901
Find similar
United Airlines
17 Oct
STL4:50 p.m.Lambert-St Louis
20h 19m
1 stop
YWG1:09 p.m.Winnipeg
24 Oct
YWG2:20 p.m.Winnipeg
20h 29m
1 stop
STL10:49 a.m.Lambert-St Louis
C$ 948
Find similar

Air Canada flights from Illinois to Winnipeg

Our best Air Canada deals on Illinois to Winnipeg flight tickets
Air Canada
3 Mar
STL4:05 p.m.Lambert-St Louis
7h 39m
1 stop
YWG11:44 p.m.Winnipeg
4 Mar
YWG7:15 a.m.Winnipeg
8h 14m
1 stop
STL3:29 p.m.Lambert-St Louis
C$ 927
Find similar
Air Canada
3 Mar
STL10:30 a.m.Lambert-St Louis
9h 58m
2 stops
YWG8:28 p.m.Winnipeg
4 Mar
YWG7:15 a.m.Winnipeg
8h 14m
1 stop
STL3:29 p.m.Lambert-St Louis
C$ 1,036
Find similar
Air Canada
3 Mar
STL11:45 a.m.Lambert-St Louis
8h 43m
2 stops
YWG8:28 p.m.Winnipeg
4 Mar
YWG6:00 a.m.Winnipeg
9h 21m
2 stops
STL3:21 p.m.Lambert-St Louis
C$ 1,047
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Winnipeg 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 September 2025.
Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 18/10

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

1 stop7h 45m

Winnipeg

Sun 26/10

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

1 stop7h 20m

C$ 216

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 18/10

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

1 stop7h 45m

Winnipeg

Sun 26/10

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

1 stop7h 20m

C$ 217

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 18/10

6:00 a.m.-12:30 a.m.

2 stops18h 30m

Winnipeg

Sun 26/10

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

1 stop7h 20m

C$ 272

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 18/10

5:45 p.m.-12:30 a.m.

2 stops30h 45m

Winnipeg

Sun 26/10

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

1 stop7h 20m

C$ 274

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 18/10

7:10 p.m.-11:27 p.m.

1 stop4h 17m

Winnipeg

Sun 26/10

8:00 a.m.-1:08 p.m.

1 stop5h 08m

C$ 770

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 11/10

8:53 a.m.-4:50 p.m.

1 stop7h 57m

Winnipeg

Wed 15/10

6:40 a.m.-5:29 p.m.

2 stops10h 49m

C$ 779

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 23/9

11:30 a.m.-10:33 p.m.

1 stop11h 03m

Winnipeg

Wed 1/10

7:00 a.m.-10:35 p.m.

1 stop15h 35m

C$ 887

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Wed 1/10

12:25 p.m.-10:33 p.m.

1 stop10h 08m

Winnipeg

Mon 6/10

4:25 p.m.-10:49 a.m.

2 stops18h 24m

C$ 901

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 3/3

4:05 p.m.-11:44 p.m.

1 stop7h 39m

Winnipeg

Wed 4/3

7:15 a.m.-3:29 p.m.

1 stop8h 14m

C$ 927

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 3/3

10:30 a.m.-8:28 p.m.

2 stops9h 58m

Winnipeg

Wed 4/3

7:15 a.m.-3:29 p.m.

1 stop8h 14m

C$ 1,036

Flights are sorted by cheapest round-trip flights first.

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

See travel insights to Winnipeg from

How to get the cheapest flight ticket from Illinois to Winnipeg

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 Winnipeg?

The cheapest month to fly to Winnipeg from Illinois is in May. Flight prices, which tend to average around C$ 374, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of May, then departing from Illinois during the month January is also very affordable. Most momondo users find prices during this month for around C$ 441.

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

Our data shows that Tuesday is the least expensive day to fly to Winnipeg. Tickets to fly out on this day can be as low as C$ 443. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Winnipeg on Saturday is C$ 1,003.

What is the cheapest time of day to depart on your flight to Winnipeg?

In the morning is the cheapest time of day to fly from Illinois to Winnipeg when you can find flight prices for as low as C$ 444. Flying to Winnipeg in the morning is an ideal time because this is during off-peak travel hours. Flights to Winnipeg are more costly in the evening, with an average ticket price of C$ 929. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Illinois to Winnipeg flight route?

Fly from Chicago O'Hare Intl to Winnipeg for the best Illinois - Winnipeg flight prices

What cabin class options are available on Illinois to Winnipeg flights?

There is only 1 cabin class available to choose from on Illinois to Winnipeg 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 Illinois to Winnipeg flights?

You could potentially save up to 47% on your flight if you consider stops on a Illinois to Winnipeg flight.

Cheap Illinois to Winnipeg flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Winnipeg

Fastest flight time

2h 30m

Direct flights

Every day

Airports in Winnipeg

1 airport
The fastest flight from Illinois to Winnipeg takes 2h 30m
Direct flights go from Illinois to Winnipeg every day.
There is 1 airport near Winnipeg: Winnipeg (YWG)
Search flight deals

  • When did momondo last update prices for flights from Illinois to Winnipeg Airport?

    Prices for flights from Illinois to Winnipeg Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Illinois to Winnipeg Airport?

  • How old do you have to be to fly from Illinois to Winnipeg Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Illinois to Winnipeg Airport.

  • What documentation or ID do you need to fly to Winnipeg Airport?

    The travel and health documents you'll need for your trip to Winnipeg Airport 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 Winnipeg Airport. 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 Illinois to Winnipeg?

Best airlines flying from Illinois to Winnipeg

Compare and see reviews for airlines that fly from Illinois to Winnipeg with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 443Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk
Morden
Portage la Prairie

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Winnipeg?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Illinois to Winnipeg . Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Illinois to Winnipeg with flexible booking policies on momondo?

Flights from Illinois to Winnipeg with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Illinois to Winnipeg?

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 Winnipeg from Illinois.

I’m not ready to book a flight from Illinois to Winnipeg right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Illinois to Winnipeg flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Winnipeg 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
Tue 9/9
Tue 16/9
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Canada