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Cheap flights from Illinois to Winnipeg from C$ 146

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 20/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
22 Mar — 29 Mar1
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 20 February 2026.

Fri 5/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 7/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 19/2C$ 333
Wed 4/38:16 p.m.
ORD
-
YWG
2 stops19h 14m
Multiple Airlines
Mon 9/38:00 a.m.
YWG
-
ORD
1 stop26h 36m
Multiple Airlines
Deal found 18/2C$ 389
Mon 11/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 1/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 19/2C$ 419
Fri 24/42:20 p.m.
ORD
-
YWG
2 stops9h 27m
WestJet
Sun 26/48:00 a.m.
YWG
-
ORD
1 stop8h 40m
WestJet
Deal found 17/2C$ 470
Mon 6/42:20 p.m.
ORD
-
YWG
1 stop19h 47m
Multiple Airlines
Mon 13/48:00 a.m.
YWG
-
ORD
1 stop27h 17m
Multiple Airlines
Deal found 20/2C$ 475
Wed 4/38:16 p.m.
ORD
-
YWG
2 stops19h 14m
Multiple Airlines
Thu 12/37:30 a.m.
YWG
-
ORD
1 stop22h 38m
Multiple Airlines
Deal found 18/2C$ 478
Tue 17/36:01 p.m.
ORD
-
YWG
2 stops29h 34m
Multiple Airlines
Tue 19/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 16/2C$ 479
Thu 14/57:30 a.m.
STL
-
YWG
1 stop6h 48m
Air Canada
Wed 20/511:00 a.m.
YWG
-
STL
1 stop9h 05m
Air Canada
Deal found 19/2C$ 553
Tue 7/48:15 p.m.
STL
-
YWG
1 stop15h 37m
United Airlines
Wed 8/42:00 p.m.
YWG
-
STL
1 stop7h 08m
United Airlines
Deal found 18/2C$ 557
Sun 24/57:30 a.m.
STL
-
YWG
1 stop8h 48m
Air Canada
Sat 30/511:00 a.m.
YWG
-
STL
1 stop9h 05m
Air Canada
Deal found 19/2C$ 587
Thu 14/56:20 a.m.
STL
-
YWG
2 stops15h 20m
WestJet
Wed 20/57:00 a.m.
YWG
-
STL
2 stops16h 21m
WestJet
Deal found 19/2C$ 602
Mon 25/51:00 p.m.
STL
-
YWG
1 stop8h 19m
Air Canada
Mon 1/611:00 a.m.
YWG
-
STL
1 stop9h 05m
Air Canada
Deal found 19/2C$ 609

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 20 February 2026.

Round-trip from

C$ 333

One-way from

C$ 146

Popular in

January

Cheapest in

May

Average price

C$ 983
WestJet
  • WestJet
  • 5/6-7/6
  • 2 total stops
  • 17h 05m total
  • Illinois to Winnipeg
Search Deals
WestJet
  • WestJet
  • 20/5
  • 1 total stop
  • 7h 25m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 29% potential increase in price (C$ 497 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease (C$ 105 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 20 February 2026.
Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.

Fly from

Illinois

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 24/4

2:20 p.m.-11:47 p.m.

2 stops9h 27m

Winnipeg

Sun 26/4

8:00 a.m.-4:40 p.m.

1 stop8h 40m

C$ 470

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 17/3

6:01 p.m.-11:35 p.m.

2 stops29h 34m

Winnipeg

Tue 19/5

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

1 stop9h 40m

C$ 479

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-9:35 a.m.

2 stops16h 05m

Winnipeg

Sun 7/6

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

1 stop9h 40m

C$ 489

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 19/8

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

1 stop7h 25m

Winnipeg

Tue 25/8

9:05 p.m.-10:21 a.m.

2 stops13h 16m

C$ 538

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Mon 25/5

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

1 stop8h 19m

Winnipeg

Sun 31/5

5:10 a.m.-12:06 p.m.

1 stop6h 56m

C$ 553

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 14/5

7:30 a.m.-2:18 p.m.

1 stop6h 48m

Winnipeg

Wed 20/5

11:00 a.m.-8:05 p.m.

1 stop9h 05m

C$ 553

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 7/4

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

1 stop15h 37m

Winnipeg

Wed 8/4

2:00 p.m.-9:47 p.m.

1 stop7h 47m

C$ 557

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 23/4

8:52 a.m.-7:09 p.m.

2 stops10h 17m

Winnipeg

Tue 28/4

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

1 stop8h 10m

C$ 585

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sun 24/5

7:30 a.m.-4:18 p.m.

1 stop8h 48m

Winnipeg

Sat 30/5

11:00 a.m.-8:05 p.m.

1 stop9h 05m

C$ 587

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 18/8

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

1 stop7h 25m

Winnipeg

Tue 25/8

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

1 stop9h 40m

C$ 617

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/2

Showing 1-10 of 41 results
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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 20 February 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 20 February 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 WestJet and Air Canada fly from Illinois to Winnipeg in about 8h 19m. The time it takes to get you to your destination can typically vary by up to 1h 08m. 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 (66%), Air Canada (66%) and United Airlines (66%).

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

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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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