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Cheap flights from Illinois to Winnipeg from C$ 182

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 26/4. 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

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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
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
C$ 440WestJet
Thu, 30 Apr - Sun, 3 May
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:05 p.m. - 7:51 p.m.
YWG
-
ORD
22h 46m
2 stops
C$ 465Multiple Airlines
Thu, 30 Apr - Mon, 4 May
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:05 p.m. - 10:39 p.m.
YWG
-
ORD
25h 34m
2 stops
C$ 469Multiple Airlines
Thu, 30 Apr - Sun, 3 May
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$ 490WestJet
Thu, 30 Apr - Sat, 2 May
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:05 p.m. - 10:46 a.m.
YWG
-
ORD
13h 41m
2 stops
C$ 491Multiple Airlines
Thu, 14 May - Tue, 19 May
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$ 516WestJet
Sun, 26 Apr - Sat, 2 May
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$ 517WestJet
Sun, 26 Apr - Sat, 2 May
Air Canada Logo
1:05 p.m. - 11:18 p.m.
STL
-
YWG
10h 13m
2 stops
Air Canada Logo
11:00 a.m. - 8:25 p.m.
YWG
-
STL
9h 25m
1 stop
C$ 554Air Canada
Mon, 4 May - Mon, 11 May
Air Canada Logo
1:05 p.m. - 11:18 p.m.
STL
-
YWG
10h 13m
2 stops
Air Canada Logo
8:10 a.m. - 8:25 p.m.
YWG
-
STL
12h 15m
2 stops
C$ 571Air Canada
Mon, 4 May - Mon, 11 May
Air Canada Logo
2:15 p.m. - 11:18 p.m.
STL
-
YWG
9h 03m
1 stop
Air Canada Logo
11:00 a.m. - 8:25 p.m.
YWG
-
STL
9h 25m
1 stop
C$ 586Air Canada
Mon, 4 May - Mon, 11 May

United Airlines flights from Illinois to Winnipeg

Our best United Airlines deals on Illinois to Winnipeg flight tickets
United Airlines
25 May
STL5:10 a.m.Lambert-St Louis
15h 47m
1 stop
YWG8:57 p.m.Winnipeg
1 Jun
YWG7:00 a.m.Winnipeg
5h 11m
1 stop
STL12:11 p.m.Lambert-St Louis
C$ 646
United Airlines
25 May
STL5:10 a.m.Lambert-St Louis
15h 47m
1 stop
YWG8:57 p.m.Winnipeg
29 May
YWG8:45 a.m.Winnipeg
11h 58m
1 stop
STL8:43 p.m.Lambert-St Louis
C$ 648
United Airlines
17 Apr
STL8:15 p.m.Lambert-St Louis
15h 37m
1 stop
YWG11:52 a.m.Winnipeg
20 Apr
YWG8:45 a.m.Winnipeg
8h 11m
1 stop
STL4:56 p.m.Lambert-St Louis
C$ 757

Air Canada flights from Illinois to Winnipeg

Our best Air Canada deals on Illinois to Winnipeg flight tickets
Air Canada
4 May
STL1:05 p.m.Lambert-St Louis
10h 13m
2 stops
YWG11:18 p.m.Winnipeg
11 May
YWG11:00 a.m.Winnipeg
9h 25m
1 stop
STL8:25 p.m.Lambert-St Louis
C$ 554
Air Canada
4 May
STL1:05 p.m.Lambert-St Louis
10h 13m
2 stops
YWG11:18 p.m.Winnipeg
11 May
YWG8:10 a.m.Winnipeg
12h 15m
2 stops
STL8:25 p.m.Lambert-St Louis
C$ 571
Air Canada
4 May
STL2:15 p.m.Lambert-St Louis
9h 03m
1 stop
YWG11:18 p.m.Winnipeg
11 May
YWG11:00 a.m.Winnipeg
9h 25m
1 stop
STL8:25 p.m.Lambert-St Louis
C$ 586

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 24 March 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
Quickest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 30/4

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

1 stop7h 25m

Winnipeg

Sun 3/5

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

1 stop9h 40m

C$ 440

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 30/4

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

1 stop7h 25m

Winnipeg

Mon 4/5

9:05 p.m.-7:51 p.m.

2 stops22h 46m

C$ 465

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 30/4

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

1 stop7h 25m

Winnipeg

Sun 3/5

9:05 p.m.-10:39 p.m.

2 stops25h 34m

C$ 469

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 30/4

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

1 stop7h 25m

Winnipeg

Sat 2/5

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

1 stop19h 35m

C$ 490

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 14/5

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

1 stop7h 25m

Winnipeg

Tue 19/5

9:05 p.m.-10:46 a.m.

2 stops13h 41m

C$ 491

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 26/4

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

1 stop7h 25m

Winnipeg

Sat 2/5

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

1 stop21h 30m

C$ 516

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 26/4

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

1 stop7h 25m

Winnipeg

Sat 2/5

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

1 stop21h 30m

C$ 517

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Mon 4/5

1:05 p.m.-11:18 p.m.

2 stops10h 13m

Winnipeg

Mon 11/5

11:00 a.m.-8:25 p.m.

1 stop9h 25m

C$ 554

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Mon 4/5

1:05 p.m.-11:18 p.m.

2 stops10h 13m

Winnipeg

Mon 11/5

8:10 a.m.-8:25 p.m.

2 stops12h 15m

C$ 571

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Mon 4/5

2:15 p.m.-11:18 p.m.

1 stop9h 03m

Winnipeg

Mon 11/5

11:00 a.m.-8:25 p.m.

1 stop9h 25m

C$ 586

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 May. Flight prices, which tend to average around C$ 390, 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 February is also very affordable. Most momondo users find prices during this month for around C$ 508.

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$ 431. 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$ 922. 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 61% 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 34m

Direct flights

Every day

Airports in Winnipeg

1 airport
The fastest flight from Illinois to Winnipeg takes 2h 34m
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.

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