Latest deals
Insights
FAQs
Price Alerts

Cheap flights from Illinois to Winnipeg from C$ 227

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 6/6. 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

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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m
1 stop
Multiple Airlines Logo
8:00 a.m. - 10:36 a.m.
YWG
-
ORD
26h 36m
1 stop
C$ 435Multiple Airlines
Mon, 16 Mar - Mon, 23 Mar
WestJet Logo
5:30 p.m. - 12:15 p.m.
ORD
-
YWG
18h 45m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 446WestJet
Mon, 11 May - Mon, 1 Jun
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:05 p.m. - 2:15 p.m.
YWG
-
ORD
17h 10m
2 stops
C$ 457Multiple Airlines
Fri, 1 May - Fri, 15 May
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.
YWG
-
ORD
8h 13m
1 stop
C$ 458WestJet
Wed, 17 Jun - Wed, 24 Jun
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 464WestJet
Fri, 5 Jun - Sun, 7 Jun
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 470WestJet
Fri, 5 Jun - Sun, 7 Jun
Multiple Airlines Logo
2:20 p.m. - 10:40 p.m.
ORD
-
YWG
8h 20m
1 stop
Multiple Airlines Logo
4:10 p.m. - 6:08 a.m.
YWG
-
ORD
13h 58m
2 stops
C$ 472Multiple Airlines
Mon, 16 Mar - Mon, 23 Mar
Air Canada Logo
7:30 a.m. - 2:18 p.m.
STL
-
YWG
6h 48m
1 stop
Air Canada Logo
11:00 a.m. - 8:05 p.m.
YWG
-
STL
9h 05m
1 stop
C$ 580Air Canada
Thu, 14 May - Wed, 20 May
United Airlines Logo
6:25 a.m. - 11:57 a.m.
STL
-
YWG
5h 32m
1 stop
United Airlines Logo
2:00 p.m. - 9:08 p.m.
YWG
-
STL
7h 08m
1 stop
C$ 584United Airlines
Sun, 22 Mar - Sun, 29 Mar
Air Canada Logo
4:05 p.m. - 11:54 p.m.
STL
-
YWG
7h 49m
1 stop
Air Canada Logo
7:00 a.m. - 3:29 p.m.
YWG
-
STL
8h 29m
1 stop
C$ 585Air Canada
Mon, 2 Mar - Wed, 4 Mar

WestJet flights from Illinois to Winnipeg

Our best WestJet deals on Illinois to Winnipeg flight tickets
WestJet
11 May
ORD5:30 p.m.Chicago O'Hare Intl
18h 45m
1 stop
YWG12:15 p.m.Winnipeg
1 Jun
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 446
WestJet
17 Jun
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
24 Jun
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
C$ 458
WestJet
5 Jun
ORD5:30 p.m.Chicago O'Hare Intl
7h 25m
1 stop
YWG12:55 a.m.Winnipeg
7 Jun
YWG7:00 a.m.Winnipeg
9h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
C$ 464

United Airlines flights from Illinois to Winnipeg

Our best United Airlines deals on Illinois to Winnipeg flight tickets
United Airlines
22 Mar
STL6:25 a.m.Lambert-St Louis
5h 32m
1 stop
YWG11:57 a.m.Winnipeg
29 Mar
YWG2:00 p.m.Winnipeg
7h 08m
1 stop
STL9:08 p.m.Lambert-St Louis
C$ 584
United Airlines
21 Mar
STL6:25 a.m.Lambert-St Louis
5h 32m
1 stop
YWG11:57 a.m.Winnipeg
28 Mar
YWG2:20 p.m.Winnipeg
8h 39m
1 stop
STL10:59 p.m.Lambert-St Louis
C$ 822
United Airlines
19 Feb
ORD9:15 a.m.Chicago O'Hare Intl
2h 42m
YWG11:57 a.m.Winnipeg
23 Feb
YWG2:20 p.m.Winnipeg
2h 25m
ORD4:45 p.m.Chicago O'Hare Intl
C$ 1,199

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 6 February 2026.
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

Mon 16/3

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

1 stop8h 20m

Winnipeg

Mon 23/3

8:00 a.m.-10:36 a.m.

1 stop26h 36m

C$ 435

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 11/5

5:30 p.m.-12:15 p.m.

1 stop18h 45m

Winnipeg

Mon 1/6

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

1 stop9h 40m

C$ 446

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/5

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

1 stop7h 25m

Winnipeg

Fri 15/5

9:05 p.m.-2:15 p.m.

2 stops17h 10m

C$ 457

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 17/6

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

1 stop7h 25m

Winnipeg

Wed 24/6

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

1 stop8h 13m

C$ 458

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

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

1 stop7h 25m

Winnipeg

Sun 7/6

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

1 stop9h 40m

C$ 464

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

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

1 stop7h 25m

Winnipeg

Sun 7/6

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

1 stop9h 40m

C$ 470

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 16/3

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

1 stop8h 20m

Winnipeg

Mon 23/3

4:10 p.m.-6:08 a.m.

2 stops13h 58m

C$ 472

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 14/5

7:30 a.m.-2:18 p.m.

1 stop6h 48m

Winnipeg

Wed 20/5

11:00 a.m.-8:05 p.m.

1 stop9h 05m

C$ 580

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sun 22/3

6:25 a.m.-11:57 a.m.

1 stop5h 32m

Winnipeg

Sun 29/3

2:00 p.m.-9:08 p.m.

1 stop7h 08m

C$ 584

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Mon 2/3

4:05 p.m.-11:54 p.m.

1 stop7h 49m

Winnipeg

Wed 4/3

7:00 a.m.-3:29 p.m.

1 stop8h 29m

C$ 585

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$ 371, 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 August is also very affordable. Most momondo users find prices during this month for around C$ 613.

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$ 438. Be sure to avoid booking your departure on a Wednesday as prices are generally higher than usual. According to our data, the average ticket price to Winnipeg on Wednesday is C$ 871.

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$ 438. 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$ 919. 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?

No. A direct flight is the cheapest option for a flight between Illinois to Winnipeg.

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 24m

Direct flights

Every day

Airports in Winnipeg

1 airport
The fastest flight from Illinois to Winnipeg takes 2h 24m
Direct flights go from Illinois to Winnipeg every day.
There is 1 airport in Winnipeg. From Illinois there are direct flights to 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 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?

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Morden
Selkirk
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
Sun 8/3
Sun 15/3
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Canada