Latest deals
Insights
FAQs
Price Alerts

Cheap flights from Illinois to Winnipeg from C$ 135

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 27/1. 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.
WestJet Logo
5:30 p.m. - 11:40 a.m.
ORD
-
YWG
18h 10m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.
YWG
-
ORD
8h 13m1 stop
C$ 354WestJet
Mon, 25 May - Mon, 1 Jun
WestJet Logo
5:30 p.m. - 8:48 p.m.
ORD
-
YWG
27h 18m2 stops
WestJet Logo
8:30 a.m. - 4:43 p.m.
YWG
-
ORD
8h 13m1 stop
C$ 361WestJet
Mon, 25 May - Mon, 1 Jun
WestJet Logo
2:20 p.m. - 10:41 p.m.
ORD
-
YWG
8h 21m1 stop
WestJet Logo
12:40 p.m. - 1:35 p.m.
YWG
-
ORD
24h 55m1 stop
C$ 364WestJet
Fri, 23 Jan - Sun, 25 Jan
Multiple Airlines Logo
6:15 a.m. - 12:43 a.m.
ORD
-
YWG
18h 28m1 stop
Multiple Airlines Logo
8:00 a.m. - 11:22 a.m.
YWG
-
ORD
27h 22m1 stop
C$ 377Multiple Airlines
Sun, 11 Jan - Mon, 19 Jan
Multiple Airlines Logo
6:00 a.m. - 12:40 a.m.
MDW
-
YWG
18h 40m2 stops
Multiple Airlines Logo
7:30 a.m. - 7:59 p.m.
YWG
-
MDW
12h 29m1 stop
C$ 380Multiple Airlines
Fri, 27 Feb - Sun, 1 Mar
WestJet Logo
5:30 p.m. - 11:33 a.m.
ORD
-
YWG
18h 03m2 stops
WestJet Logo
7:00 a.m. - 4:43 p.m.
YWG
-
ORD
9h 43m2 stops
C$ 386WestJet
Mon, 25 May - Mon, 1 Jun
Multiple Airlines Logo
2:42 p.m. - 3:07 p.m.
ORD
-
YWG
24h 25m1 stop
Multiple Airlines Logo
12:10 p.m. - 11:22 a.m.
YWG
-
ORD
23h 12m2 stops
C$ 387Multiple Airlines
Thu, 29 Jan - Thu, 5 Feb
Air Canada Logo
1:00 p.m. - 9:19 p.m.
STL
-
YWG
8h 19m1 stop
Air Canada Logo
2:00 p.m. - 8:04 p.m.
YWG
-
STL
6h 04m1 stop
C$ 589Air Canada
Thu, 14 May - Wed, 20 May
Air Canada Logo
4:05 p.m. - 11:54 p.m.
STL
-
YWG
7h 49m1 stop
Air Canada Logo
7:00 a.m. - 3:29 p.m.
YWG
-
STL
8h 29m1 stop
C$ 593Air Canada
Sat, 10 Jan - Sat, 17 Jan
United Airlines Logo
6:30 a.m. - 11:57 a.m.
STL
-
YWG
5h 27m1 stop
United Airlines Logo
2:20 p.m. - 9:13 p.m.
YWG
-
STL
6h 53m1 stop
C$ 595United Airlines
Tue, 13 Jan - Tue, 20 Jan

WestJet flights from Illinois to Winnipeg

Our best WestJet deals on Illinois to Winnipeg flight tickets
WestJet
25 May
ORD5:30 p.m.Chicago O'Hare Intl
18h 10m
1 stop
YWG11:40 a.m.Winnipeg
1 Jun
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
C$ 354
Find similar
WestJet
25 May
ORD5:30 p.m.Chicago O'Hare Intl
27h 18m
2 stops
YWG8:48 p.m.Winnipeg
1 Jun
YWG8:30 a.m.Winnipeg
8h 13m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
C$ 361
Find similar
WestJet
23 Jan
ORD2:20 p.m.Chicago O'Hare Intl
8h 21m
1 stop
YWG10:41 p.m.Winnipeg
25 Jan
YWG12:40 p.m.Winnipeg
24h 55m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
C$ 364
Find similar

United Airlines flights from Illinois to Winnipeg

Our best United Airlines deals on Illinois to Winnipeg flight tickets
United Airlines
13 Jan
STL6:30 a.m.Lambert-St Louis
5h 27m
1 stop
YWG11:57 a.m.Winnipeg
20 Jan
YWG2:20 p.m.Winnipeg
6h 53m
1 stop
STL9:13 p.m.Lambert-St Louis
C$ 595
Find similar
United Airlines
12 Jan
STL8:05 a.m.Lambert-St Louis
13h 39m
2 stops
YWG9:44 p.m.Winnipeg
15 Jan
YWG7:05 a.m.Winnipeg
8h 24m
1 stop
STL3:29 p.m.Lambert-St Louis
C$ 710
Find similar
United Airlines
24 Dec
ORD9:05 p.m.Chicago O'Hare Intl
26h 49m
2 stops
YWG11:54 p.m.Winnipeg
30 Dec
YWG2:20 p.m.Winnipeg
2h 43m
ORD5:03 p.m.Chicago O'Hare Intl
C$ 1,205
Find similar

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 December 2025.
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 25/5

5:30 p.m.-11:40 a.m.

1 stop18h 10m

Winnipeg

Mon 1/6

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

1 stop8h 13m

C$ 354

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 25/5

5:30 p.m.-8:48 p.m.

2 stops27h 18m

Winnipeg

Mon 1/6

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

1 stop8h 13m

C$ 361

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 23/1

2:20 p.m.-10:41 p.m.

1 stop8h 21m

Winnipeg

Sun 25/1

12:40 p.m.-1:35 p.m.

1 stop24h 55m

C$ 364

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 11/1

6:15 a.m.-12:43 a.m.

1 stop18h 28m

Winnipeg

Mon 19/1

8:00 a.m.-11:22 a.m.

1 stop27h 22m

C$ 377

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 27/2

6:00 a.m.-12:40 a.m.

2 stops18h 40m

Winnipeg

Sun 1/3

7:30 a.m.-7:59 p.m.

1 stop12h 29m

C$ 380

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 25/5

5:30 p.m.-11:33 a.m.

2 stops18h 03m

Winnipeg

Mon 1/6

7:00 a.m.-4:43 p.m.

2 stops9h 43m

C$ 386

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 29/1

2:42 p.m.-3:07 p.m.

1 stop24h 25m

Winnipeg

Thu 5/2

12:10 p.m.-11:22 a.m.

2 stops23h 12m

C$ 387

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 14/5

1:00 p.m.-9:19 p.m.

1 stop8h 19m

Winnipeg

Wed 20/5

2:00 p.m.-8:04 p.m.

1 stop6h 04m

C$ 589

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 10/1

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

1 stop7h 49m

Winnipeg

Sat 17/1

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

1 stop8h 29m

C$ 593

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 13/1

6:30 a.m.-11:57 a.m.

1 stop5h 27m

Winnipeg

Tue 20/1

2:20 p.m.-9:13 p.m.

1 stop6h 53m

C$ 595

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$ 373, 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 January is also very affordable. Most momondo users find prices during this month for around C$ 439.

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$ 441. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Winnipeg on Saturday is C$ 999.

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$ 441. 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$ 925. 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 47% 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, Wed, 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, Wednesday, 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

  • 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
Wed 14/1
Wed 21/1
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Canada