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Cheap flights from Illinois to Winnipeg from C$ 216

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 5/6. 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

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Find the cheapest flights from Illinois to Winnipeg

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:10 p.m. - 4:40 p.m.
YWG
-
ORD
21h 30m
1 stop
C$ 488WestJet
Fri, 5 Jun - Sun, 7 Jun
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
2:55 p.m. - 4:40 p.m.
YWG
-
ORD
25h 45m
1 stop
C$ 492WestJet
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$ 495WestJet
Mon, 19 Oct - Fri, 23 Oct
WestJet Logo
5:30 p.m. - 11:10 a.m.
ORD
-
YWG
17h 40m
1 stop
WestJet Logo
6:15 a.m. - 1:35 p.m.
YWG
-
ORD
7h 20m
1 stop
C$ 516WestJet
Thu, 22 Oct - Mon, 26 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
2:55 p.m. - 4:40 p.m.
YWG
-
ORD
25h 45m
1 stop
C$ 525WestJet
Fri, 5 Jun - Sun, 7 Jun
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
6:00 a.m. - 12:25 p.m.
YWG
-
ORD
6h 25m
1 stop
C$ 552Multiple Airlines
Thu, 22 Oct - Tue, 27 Oct
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:20 a.m. - 7:38 p.m.
YWG
-
ORD
10h 18m
1 stop
C$ 562Multiple Airlines
Sat, 6 Jun - Sun, 7 Jun
Air Canada Logo
12:10 p.m. - 9:19 p.m.
STL
-
YWG
9h 09m
1 stop
Air Canada Logo
10:55 a.m. - 6:42 p.m.
YWG
-
STL
7h 47m
1 stop
C$ 875Air Canada
Sun, 16 Aug - Sat, 22 Aug
United Airlines Logo
5:29 p.m. - 10:38 p.m.
STL
-
YWG
5h 09m
1 stop
United Airlines Logo
7:00 a.m. - 12:11 p.m.
YWG
-
STL
5h 11m
1 stop
C$ 886United Airlines
Fri, 12 Jun - Sat, 20 Jun
Air Canada Logo
2:15 p.m. - 9:28 p.m.
STL
-
YWG
7h 13m
1 stop
Air Canada Logo
5:10 a.m. - 12:21 p.m.
YWG
-
STL
7h 11m
1 stop
C$ 889Air Canada
Wed, 10 Jun - Sat, 20 Jun

Porter Airlines flights from Illinois to Winnipeg

Our best Porter Airlines deals on Illinois to Winnipeg flight tickets
Porter Airlines
4 Jun
MDW10:15 a.m.Chicago Midway
9h 34m
1 stop
YWG7:49 p.m.Winnipeg
8 Jun
YWG8:45 p.m.Winnipeg
12h 50m
1 stop
MDW9:35 a.m.Chicago Midway
C$ 729
Porter Airlines
26 Jun
MDW3:20 p.m.Chicago Midway
26h 43m
2 stops
YWG6:03 p.m.Winnipeg
3 Jul
YWG4:15 p.m.Winnipeg
17h 25m
2 stops
MDW9:40 a.m.Chicago Midway
C$ 866
Porter Airlines
24 Jun
MDW10:25 a.m.Chicago Midway
31h 33m
2 stops
YWG5:58 p.m.Winnipeg
28 Jun
YWG11:40 a.m.Winnipeg
26h 55m
2 stops
MDW2:35 p.m.Chicago Midway
C$ 881

Air Canada flights from Illinois to Winnipeg

Our best Air Canada deals on Illinois to Winnipeg flight tickets
Air Canada
16 Aug
STL12:10 p.m.Lambert-St Louis
9h 09m
1 stop
YWG9:19 p.m.Winnipeg
22 Aug
YWG10:55 a.m.Winnipeg
7h 47m
1 stop
STL6:42 p.m.Lambert-St Louis
C$ 875
Air Canada
10 Jun
STL2:15 p.m.Lambert-St Louis
7h 13m
1 stop
YWG9:28 p.m.Winnipeg
20 Jun
YWG5:10 a.m.Winnipeg
7h 11m
1 stop
STL12:21 p.m.Lambert-St Louis
C$ 889
Air Canada
22 Aug
STL12:10 p.m.Lambert-St Louis
9h 09m
1 stop
YWG9:19 p.m.Winnipeg
26 Aug
YWG8:15 a.m.Winnipeg
10h 27m
2 stops
STL6:42 p.m.Lambert-St Louis
C$ 894

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 10 May 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

Cheapest round-trip

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

7:10 p.m.-4:40 p.m.

1 stop21h 30m

C$ 488

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

2:55 p.m.-4:40 p.m.

1 stop25h 45m

C$ 492

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 19/10

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

1 stop7h 25m

Winnipeg

Fri 23/10

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

1 stop9h 40m

C$ 495

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 22/10

5:30 p.m.-11:10 a.m.

1 stop17h 40m

Winnipeg

Mon 26/10

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

1 stop7h 20m

C$ 516

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

2:55 p.m.-4:40 p.m.

1 stop25h 45m

C$ 525

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 22/10

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

1 stop7h 25m

Winnipeg

Tue 27/10

6:00 a.m.-12:25 p.m.

1 stop6h 25m

C$ 552

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 6/6

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

1 stop7h 25m

Winnipeg

Sun 7/6

9:20 a.m.-7:38 p.m.

1 stop10h 18m

C$ 562

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sun 16/8

12:10 p.m.-9:19 p.m.

1 stop9h 09m

Winnipeg

Sat 22/8

10:55 a.m.-6:42 p.m.

1 stop7h 47m

C$ 875
Quickest round-trip

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Fri 12/6

5:29 p.m.-10:38 p.m.

1 stop5h 09m

Winnipeg

Sat 20/6

7:00 a.m.-12:11 p.m.

1 stop5h 11m

C$ 886

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Wed 10/6

2:15 p.m.-9:28 p.m.

1 stop7h 13m

Winnipeg

Sat 20/6

5:10 a.m.-12:21 p.m.

1 stop7h 11m

C$ 889

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 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 February. Flight prices, which tend to average around C$ 85, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of February, then departing from Illinois during the month October is also very affordable. Most momondo users find prices during this month for around C$ 111.

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$ 429. 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

Can stopping save me money on Illinois to Winnipeg flights?

You could potentially save up to 50% 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 24m

Direct flights

Mon, Tue, Wed, Thu, Fri and Sat

Airports in Winnipeg

1 airport
The fastest flight from Illinois to Winnipeg takes 2h 24m
Direct flights go from Illinois to Winnipeg on Monday, Tuesday, Wednesday, Thursday, Friday and Saturday. There are no airlines offering direct flights.
There is 1 airport in Winnipeg. From Illinois there are direct flights to Winnipeg (YWG).
Search flight deals

Frequently asked questions about flying from Illinois to Winnipeg

  • 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.

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