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Cheap flights from Illinois to Winnipeg from C$ 280

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 12/8. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Illinois to Winnipeg

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:20 p.m. - 12:55 a.m.
ORD
-
YWG
9h 35m
1 stop
Multiple Airlines Logo
11:15 a.m. - 11:00 a.m.
YWG
-
ORD
23h 45m
2 stops
C$ 474Multiple Airlines
Tue, 22 Sep - Sat, 26 Sep
Multiple Airlines Logo
3:20 p.m. - 12:55 a.m.
ORD
-
YWG
9h 35m
1 stop
Multiple Airlines Logo
9:20 a.m. - 11:00 a.m.
YWG
-
ORD
25h 40m
1 stop
C$ 484Multiple Airlines
Tue, 22 Sep - Sat, 26 Sep
Porter Airlines Logo
3:20 p.m. - 7:49 p.m.
ORD
-
YWG
28h 29m
1 stop
Porter Airlines Logo
4:15 p.m. - 11:00 a.m.
YWG
-
ORD
18h 45m
2 stops
C$ 485Porter Airlines
Sun, 20 Sep - Sat, 26 Sep
Porter Airlines Logo
3:20 p.m. - 7:49 p.m.
ORD
-
YWG
28h 29m
1 stop
Porter Airlines Logo
9:20 a.m. - 11:00 a.m.
YWG
-
ORD
25h 40m
1 stop
C$ 494Porter Airlines
Sun, 20 Sep - Sat, 26 Sep
Multiple Airlines Logo
9:50 a.m. - 11:20 p.m.
ORD
-
YWG
13h 30m
1 stop
Multiple Airlines Logo
11:15 a.m. - 9:35 p.m.
YWG
-
ORD
10h 20m
2 stops
C$ 524Multiple Airlines
Fri, 28 Aug - Tue, 8 Sep
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
11:15 a.m. - 11:00 a.m.
YWG
-
ORD
23h 45m
2 stops
C$ 536Multiple Airlines
Sun, 6 Sep - Sun, 13 Sep
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
9:05 p.m. - 4:40 p.m.
YWG
-
ORD
19h 35m
1 stop
C$ 553WestJet
Sun, 6 Sep - Sun, 13 Sep
WestJet Logo
11:13 a.m. - 11:30 p.m.
STL
-
YWG
12h 17m
1 stop
WestJet Logo
5:42 p.m. - 11:26 p.m.
YWG
-
STL
5h 44m
1 stop
C$ 871WestJet
Thu, 13 Aug - Wed, 19 Aug
Air Canada Logo
12:10 p.m. - 9:14 p.m.
STL
-
YWG
9h 04m
1 stop
Air Canada Logo
10:50 a.m. - 6:41 p.m.
YWG
-
STL
7h 51m
1 stop
C$ 872Air Canada
Sat, 19 Sep - Tue, 22 Sep
Air Canada Logo
8:55 a.m. - 4:27 p.m.
STL
-
YWG
7h 32m
1 stop
Air Canada Logo
10:50 a.m. - 6:41 p.m.
YWG
-
STL
7h 51m
1 stop
C$ 879Air Canada
Mon, 21 Sep - Wed, 23 Sep

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Air Canada flights from Illinois to Winnipeg

Our best Air Canada deals on Illinois to Winnipeg flight tickets
Air Canada
12 Sep
ORD3:45 p.m.Chicago O'Hare Intl
5h 42m
1 stop
YWG9:27 p.m.Winnipeg
19 Sep
YWG12:20 p.m.Winnipeg
7h 28m
1 stop
ORD7:48 p.m.Chicago O'Hare Intl
C$ 741
Air Canada
19 Sep
STL12:10 p.m.Lambert-St Louis
9h 04m
1 stop
YWG9:14 p.m.Winnipeg
22 Sep
YWG10:50 a.m.Winnipeg
7h 51m
1 stop
STL6:41 p.m.Lambert-St Louis
C$ 872
Air Canada
21 Sep
STL8:55 a.m.Lambert-St Louis
7h 32m
1 stop
YWG4:27 p.m.Winnipeg
23 Sep
YWG10:50 a.m.Winnipeg
7h 51m
1 stop
STL6:41 p.m.Lambert-St Louis
C$ 879

Porter Airlines flights from Illinois to Winnipeg

Our best Porter Airlines deals on Illinois to Winnipeg flight tickets
Porter Airlines
20 Sep
ORD3:20 p.m.Chicago O'Hare Intl
28h 29m
1 stop
YWG7:49 p.m.Winnipeg
26 Sep
YWG4:15 p.m.Winnipeg
18h 45m
2 stops
ORD11:00 a.m.Chicago O'Hare Intl
C$ 485
Porter Airlines
20 Sep
ORD3:20 p.m.Chicago O'Hare Intl
28h 29m
1 stop
YWG7:49 p.m.Winnipeg
26 Sep
YWG9:20 a.m.Winnipeg
25h 40m
1 stop
ORD11:00 a.m.Chicago O'Hare Intl
C$ 494
Porter Airlines
6 Aug
MDW3:15 p.m.Chicago Midway
19h 28m
2 stops
YWG10:43 a.m.Winnipeg
13 Aug
YWG4:15 p.m.Winnipeg
17h 30m
2 stops
MDW9:45 a.m.Chicago Midway
C$ 848

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 25 June 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

Tue 22/9

3:20 p.m.-12:55 a.m.

1 stop9h 35m

Winnipeg

Sat 26/9

11:15 a.m.-11:00 a.m.

2 stops23h 45m

C$ 474

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 22/9

3:20 p.m.-12:55 a.m.

1 stop9h 35m

Winnipeg

Sat 26/9

9:20 a.m.-11:00 a.m.

1 stop25h 40m

C$ 484

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 20/9

3:20 p.m.-7:49 p.m.

1 stop28h 29m

Winnipeg

Sat 26/9

4:15 p.m.-11:00 a.m.

2 stops18h 45m

C$ 485

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 20/9

3:20 p.m.-7:49 p.m.

1 stop28h 29m

Winnipeg

Sat 26/9

9:20 a.m.-11:00 a.m.

1 stop25h 40m

C$ 494

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 28/8

9:50 a.m.-11:20 p.m.

1 stop13h 30m

Winnipeg

Tue 8/9

11:15 a.m.-9:35 p.m.

2 stops10h 20m

C$ 524

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 6/9

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

1 stop7h 25m

Winnipeg

Sun 13/9

11:15 a.m.-11:00 a.m.

2 stops23h 45m

C$ 536

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 6/9

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

1 stop7h 25m

Winnipeg

Sun 13/9

9:05 p.m.-4:40 p.m.

1 stop19h 35m

C$ 553

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 13/8

11:13 a.m.-11:30 p.m.

1 stop12h 17m

Winnipeg

Wed 19/8

5:42 p.m.-11:26 p.m.

1 stop5h 44m

C$ 871

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 19/9

12:10 p.m.-9:14 p.m.

1 stop9h 04m

Winnipeg

Tue 22/9

10:50 a.m.-6:41 p.m.

1 stop7h 51m

C$ 872
Quickest round-trip

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Mon 21/9

8:55 a.m.-4:27 p.m.

1 stop7h 32m

Winnipeg

Wed 23/9

10:50 a.m.-6:41 p.m.

1 stop7h 51m

C$ 879

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$ 88, 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$ 115.

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$ 447. 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$ 956. 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 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

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

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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