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Cheap flights from Illinois to Winnipeg from C$ 186

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 2/9. 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.
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 400WestJet
Tue, 1 Sep - Sat, 5 Sep
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 404WestJet
Thu, 17 Sep - Sun, 20 Sep
Multiple Airlines Logo
2:41 p.m. - 8:15 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
29h 34m2 stops Denver Intl Calgary
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 415Multiple Airlines
Wed, 2 Sep - Fri, 11 Sep
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 428WestJet
Mon, 31 Aug - Sun, 6 Sep
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 429WestJet
Sun, 27 Sep - Sun, 4 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 435WestJet
Tue, 29 Sep - Tue, 6 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 436WestJet
Mon, 28 Sep - Mon, 5 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 439WestJet
Mon, 28 Sep - Mon, 5 Oct
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 443WestJet
Fri, 11 Sep - Fri, 18 Sep
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
C$ 446WestJet
Wed, 2 Sep - Sat, 5 Sep

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Porter Airlines flights from Illinois to Winnipeg

Our best Porter Airlines deals on Illinois to Winnipeg flight tickets
Porter Airlines
10 Sep
MDW11:45 a.m.Chicago Midway
8h 04m
1 stop
YWG7:49 p.m.Winnipeg
13 Sep
YWG8:45 p.m.Winnipeg
14h 15m
1 stop
MDW11:00 a.m.Chicago Midway
C$ 542
Porter Airlines
25 Aug
MDW3:15 p.m.Chicago Midway
28h 39m
1 stop
YWG7:54 p.m.Winnipeg
1 Sep
YWG11:15 a.m.Winnipeg
27h 20m
2 stops
MDW2:35 p.m.Chicago Midway
C$ 708
Porter Airlines
25 Sep
MDW11:45 a.m.Chicago Midway
30h 13m
2 stops
YWG5:58 p.m.Winnipeg
28 Sep
YWG11:15 a.m.Winnipeg
27h 20m
2 stops
MDW2:35 p.m.Chicago Midway
C$ 876

Air Canada flights from Illinois to Winnipeg

Our best Air Canada deals on Illinois to Winnipeg flight tickets
Air Canada
7 Sep
STL8:55 a.m.Lambert-St Louis
7h 35m
1 stop
YWG4:30 p.m.Winnipeg
14 Sep
YWG2:05 p.m.Winnipeg
6h 15m
1 stop
STL8:20 p.m.Lambert-St Louis
C$ 883
Air Canada
13 Nov
STL6:00 a.m.Lambert-St Louis
6h 23m
1 stop
YWG12:23 p.m.Winnipeg
21 Nov
YWG7:15 a.m.Winnipeg
8h 11m
1 stop
STL3:26 p.m.Lambert-St Louis
C$ 974
Air Canada
21 Sep
STL12:10 p.m.Lambert-St Louis
9h 04m
1 stop
YWG9:14 p.m.Winnipeg
23 Sep
YWG10:50 a.m.Winnipeg
7h 51m
1 stop
STL6:41 p.m.Lambert-St Louis
C$ 1,052

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 15 August 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 Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 1/9

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

1 stop7h 25m

Winnipeg

Sat 5/9

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

1 stop9h 40m

C$ 400

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 17/9

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

1 stop7h 25m

Winnipeg

Sun 20/9

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

1 stop9h 40m

C$ 404

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 2/9

2:41 p.m.-8:15 p.m.

2 stops29h 34m

Winnipeg

Fri 11/9

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

1 stop9h 40m

C$ 415

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 31/8

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

1 stop7h 25m

Winnipeg

Sun 6/9

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

1 stop9h 40m

C$ 428

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 27/9

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

1 stop7h 25m

Winnipeg

Sun 4/10

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

1 stop9h 40m

C$ 429

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 29/9

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

1 stop7h 25m

Winnipeg

Tue 6/10

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

1 stop9h 40m

C$ 435

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 28/9

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

1 stop7h 25m

Winnipeg

Mon 5/10

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

1 stop9h 40m

C$ 436

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 28/9

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

1 stop7h 25m

Winnipeg

Mon 5/10

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

1 stop9h 40m

C$ 439

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 11/9

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

1 stop7h 25m

Winnipeg

Fri 18/9

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

1 stop9h 40m

C$ 443

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 2/9

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

1 stop7h 25m

Winnipeg

Sat 5/9

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

1 stop9h 40m

C$ 446

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 September. Flight prices, which tend to average around C$ 604, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of September, then departing from Illinois during the month October is also very affordable. Most momondo users find prices during this month for around C$ 681.

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 are 2 cabin classes 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

Mon, Tue, Thu, Fri, Sat and Sun

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, Thursday, Friday, Saturday and Sunday. 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
Portage la Prairie
Morden
Selkirk

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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