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Cheap flights from Illinois to Winnipeg from C$ 182

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 26/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
22 Apr — 29 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 23 March 2026.

Thu 30/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 3/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 20/3C$ 440
Fri 1/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 8/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 18/3C$ 451
Thu 30/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Mon 4/59:05 p.m.
YWG
-
ORD
2 stops22h 46m
Multiple Airlines
Deal found 20/3C$ 465
Thu 30/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sun 3/59:05 p.m.
YWG
-
ORD
2 stops25h 34m
Multiple Airlines
Deal found 20/3C$ 469
Sun 3/55:30 p.m.
ORD
-
YWG
1 stop18h 45m
WestJet
Sun 10/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 19/3C$ 487
Thu 30/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 2/59:05 p.m.
YWG
-
ORD
1 stop19h 35m
WestJet
Deal found 20/3C$ 490
Thu 14/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Tue 19/59:05 p.m.
YWG
-
ORD
2 stops13h 41m
Multiple Airlines
Deal found 22/3C$ 491
Sun 26/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 2/57:10 p.m.
YWG
-
ORD
1 stop21h 30m
WestJet
Deal found 22/3C$ 516
Thu 30/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Fri 1/59:20 a.m.
YWG
-
ORD
1 stop6h 58m
Multiple Airlines
Deal found 20/3C$ 523
Thu 30/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sat 2/56:15 a.m.
YWG
-
ORD
2 stops27h 21m
Multiple Airlines
Deal found 20/3C$ 528
Wed 3/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sun 7/69:05 p.m.
YWG
-
ORD
2 stops37h 41m
Multiple Airlines
Deal found 20/3C$ 531
Mon 4/51:05 p.m.
STL
-
YWG
2 stops10h 13m
Air Canada
Mon 11/511:00 a.m.
YWG
-
STL
1 stop9h 25m
Air Canada
Deal found 19/3C$ 554

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 23 March 2026.

Round-trip from

C$ 440

One-way from

C$ 182

Popular in

January

Cheapest in

May

Average price

C$ 977

Good one-way deal

C$ 478 or less
WestJet
  • WestJet
  • 30/4-3/5
  • 2 total stops
  • 17h 05m total
  • Illinois to Winnipeg
Search Deals
WestJet
  • WestJet
  • 26/4
  • 1 total stop
  • 7h 25m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 23% potential increase in price (C$ 344 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease (C$ 111 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a one-way flight from Illinois to Winnipeg.
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 23 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

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

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 20/4

11:00 a.m.-11:32 a.m.

1 stop24h 32m

Winnipeg

Mon 27/4

8:10 p.m.-10:15 a.m.

1 stop14h 05m

C$ 583

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 14/5

6:45 a.m.-5:15 p.m.

2 stops10h 30m

Winnipeg

Wed 20/5

7:00 a.m.-11:21 p.m.

2 stops16h 21m

C$ 615

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Mon 25/5

6:04 p.m.-2:25 p.m.

2 stops20h 21m

Winnipeg

Fri 29/5

7:00 a.m.-11:21 p.m.

2 stops16h 21m

C$ 615

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 14/5

10:25 a.m.-7:49 p.m.

1 stop9h 24m

Winnipeg

Tue 19/5

9:05 p.m.-11:09 a.m.

2 stops14h 04m

C$ 624

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 14/5

6:21 a.m.-2:55 p.m.

1 stop8h 34m

Winnipeg

Wed 20/5

5:41 p.m.-11:21 p.m.

1 stop5h 40m

C$ 632

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 12/5

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

1 stop7h 13m

Winnipeg

Sat 16/5

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

1 stop9h 25m

C$ 642

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Fri 22/5

6:21 a.m.-9:40 p.m.

2 stops15h 19m

Winnipeg

Mon 25/5

7:00 a.m.-11:21 p.m.

2 stops16h 21m

C$ 642

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Mon 25/5

5:10 a.m.-8:57 p.m.

1 stop15h 47m

Winnipeg

Mon 1/6

2:00 p.m.-9:16 p.m.

1 stop7h 16m

C$ 646

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Wed 6/5

8:30 p.m.-11:52 a.m.

1 stop15h 22m

Winnipeg

Wed 13/5

2:00 p.m.-6:53 p.m.

1 stop4h 53m

C$ 646

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/3

Showing 1-10 of 54 resultsSorted by cheapest first
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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 23 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.

Weekly flight availability from Illinois to Winnipeg

Explore weekly flight availability from Illinois to Winnipeg. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 23 March 2026.

The most flights from USIL to YWG are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

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 Delta fly from Illinois to Winnipeg in about 8h 34m. The time it takes to get you to your destination can typically vary by up to 1h 56m. 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 (64%), Air Canada (64%) and United Airlines (64%).

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay C$ 489 for a flight from Illinois to Winnipeg. The cheapest flight overall is C$ 227 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at C$ 469.

  • 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

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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.

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