Find flights
Deals
When to book
FAQs

Cheap flights from Illinois to Winnipeg from C$ 135

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
3 Apr — 10 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Illinois to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from Illinois to Winnipeg
Explore the most affordable flight options available from Illinois to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 4 March 2026.

Tue 28/46:08 p.m.
ORD
-
YWG
2 stops21h 17m
Multiple Airlines
Thu 7/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 2/3C$ 339
Fri 15/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Tue 19/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 4/3C$ 346
Fri 24/42:20 p.m.
ORD
-
YWG
1 stop8h 20m
Multiple Airlines
Mon 27/49:05 p.m.
YWG
-
ORD
2 stops19h 55m
Multiple Airlines
Deal found 1/3C$ 359
Wed 22/411:07 a.m.
ORD
-
YWG
2 stops13h 33m
Multiple Airlines
Sun 26/48:00 a.m.
YWG
-
ORD
1 stop8h 40m
Multiple Airlines
Deal found 4/3C$ 370
Tue 21/46:08 p.m.
ORD
-
YWG
1 stop21h 01m
Multiple Airlines
Mon 27/49:05 p.m.
YWG
-
ORD
2 stops12h 57m
Multiple Airlines
Deal found 1/3C$ 376
Tue 21/46:08 p.m.
ORD
-
YWG
1 stop21h 01m
Multiple Airlines
Wed 29/49:05 p.m.
YWG
-
ORD
2 stops25h 34m
Multiple Airlines
Deal found 1/3C$ 383
Sat 5/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 11/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 1/3C$ 387
Thu 23/44:28 p.m.
ORD
-
YWG
1 stop22h 41m
Multiple Airlines
Mon 27/49:05 p.m.
YWG
-
ORD
2 stops19h 55m
Multiple Airlines
Deal found 1/3C$ 392
Thu 23/411:00 a.m.
MDW
-
YWG
1 stop21h 40m
Multiple Airlines
Sun 26/49:05 p.m.
YWG
-
MDW
2 stops22h 26m
Multiple Airlines
Deal found 3/3C$ 410
Wed 22/46:15 a.m.
MDW
-
YWG
1 stop8h 54m
Multiple Airlines
Sun 26/49:05 p.m.
YWG
-
MDW
2 stops22h 26m
Multiple Airlines
Deal found 3/3C$ 411
Sat 18/44:28 p.m.
ORD
-
YWG
1 stop22h 41m
Multiple Airlines
Sat 25/49:00 p.m.
YWG
-
ORD
1 stop19h 40m
Multiple Airlines
Deal found 4/3C$ 414
Thu 10/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 14/97:10 p.m.
YWG
-
ORD
1 stop21h 30m
WestJet
Deal found 3/3C$ 415

Find flight deals from Illinois to Winnipeg

Keep the following information in mind while searching for Illinois to Winnipeg flight deals. Data was last updated 4 March 2026.

Round-trip from

C$ 339

One-way from

C$ 135

Popular in

January

Cheapest in

May

Average price

C$ 973
WestJet
  • WestJet
  • 28/4-7/5
  • 3 total stops
  • 30h 57m total
  • Illinois to Winnipeg
Search Deals
10/5
  • 10/5
  • 2 total stops
  • 34h 24m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 29% potential increase in price (C$ 492 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease (C$ 104 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights 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, Cheapflights users made 629,999 searches. Data last updated 4 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

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 14/5

7:05 a.m.-2:18 p.m.

1 stop7h 13m

Winnipeg

Wed 20/5

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

1 stop9h 25m

C$ 511

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Fri 17/4

9:55 p.m.-3:09 p.m.

2 stops41h 14m

Winnipeg

Fri 24/4

7:30 a.m.-6:50 a.m.

1 stop23h 20m

C$ 551

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 14/4

6:19 a.m.-10:56 a.m.

1 stop4h 37m

Winnipeg

Tue 21/4

6:40 a.m.-11:32 a.m.

1 stop4h 52m

C$ 556

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 7/4

6:30 a.m.-11:52 a.m.

1 stop5h 22m

Winnipeg

Wed 8/4

2:00 p.m.-9:13 p.m.

1 stop7h 13m

C$ 556

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Wed 15/4

6:30 a.m.-11:52 a.m.

1 stop5h 22m

Winnipeg

Wed 22/4

2:00 p.m.-9:13 p.m.

1 stop7h 13m

C$ 556

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 14/4

12:45 p.m.-12:39 a.m.

2 stops11h 54m

Winnipeg

Tue 21/4

12:20 p.m.-11:13 p.m.

2 stops10h 53m

C$ 574

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 16/4

8:15 p.m.-11:52 a.m.

1 stop15h 37m

Winnipeg

Thu 23/4

2:00 p.m.-9:52 p.m.

1 stop7h 52m

C$ 586

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 23/7

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

1 stop7h 25m

Winnipeg

Fri 31/7

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

2 stops9h 40m

C$ 709

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 23/4

6:25 a.m.-10:56 a.m.

1 stop4h 31m

Winnipeg

Tue 28/4

12:10 p.m.-8:20 p.m.

1 stop8h 10m

C$ 730

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 8/4

8:06 a.m.-3:30 p.m.

1 stop7h 24m

Winnipeg

Thu 9/4

12:10 p.m.-7:32 p.m.

1 stop7h 22m

C$ 749

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 50 resultsSorted by cheapest first
1
2
3
...
5

Best time to book a flight from Illinois to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Illinois with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Winnipeg

What is the cheapest time of day to fly from IL to YWG?

Find hourly flight availability from Illinois to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 4 March 2026.

When flying from Illinois to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Illinois?

    Winnipeg (YWG), located 7.3 km from the city centre, is the airport you fly into when you book flights from Illinois to Winnipeg.

  • How long is the flight from Illinois to Winnipeg?

    Airlines like Air Canada, WestJet, and Porter Airlines fly from Illinois to Winnipeg in about 7h 13m. The time it takes to get you to your destination can typically vary by up to 12m. There are 1353 km between Illinois and Winnipeg. This flight may include one or multiple stops.

  • What are the most popular routes from Illinois to Winnipeg?

    The most popular route from Illinois to Winnipeg is Chicago O'Hare Intl - Winnipeg. You may also consider Chicago Midway - Winnipeg or Lambert-St Louis - Winnipeg.

  • What are the most reliable airlines from Illinois to Winnipeg?

    The top 3 most reliable airlines when flying from Illinois to Winnipeg are SkyWest Airlines (67%), Air Canada (67%) and United Airlines (67%).

  • Can I find deals for flights from Illinois to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Illinois to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Winnipeg.

  • Can I find deals for business class flights from Illinois to Winnipeg?

    Yes. Cheapflights offers flight deals from Illinois to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk
Portage la Prairie

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Illinois to Winnipeg?

Cheapflights makes it easy to find Illinois to Winnipeg flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Illinois to Winnipeg?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Winnipeg from Illinois.

Can Cheapflights find flights from Illinois to Winnipeg with no change fees?

Yes! Cheapflights helps users easily find flights from Illinois to Winnipeg with no change fees.

Can Cheapflights notify me if prices for flights from Illinois to Winnipeg become cheaper?

Yes! Start tracking prices for Illinois to Winnipeg flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.