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Cheap flights from Illinois to Winnipeg from C$ 218

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 18/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
23 Aug — 30 Aug1
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 24 July 2026.

Fri 25/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 28/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 23/7C$ 472
Fri 2/105:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 10/109:05 p.m.
YWG
-
ORD
1 stop19h 35m
WestJet
Deal found 23/7C$ 510
Fri 23/105:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sun 25/107:00 a.m.
YWG
-
ORD
1 stop7h 20m
Multiple Airlines
Deal found 23/7C$ 526
Tue 18/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Mon 24/89:05 p.m.
YWG
-
ORD
2 stops22h 54m
Multiple Airlines
Deal found 21/7C$ 529
Thu 24/97:45 a.m.
ORD
-
YWG
2 stops17h 10m
Multiple Airlines
Mon 28/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 21/7C$ 531
Wed 2/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 5/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 22/7C$ 534
Thu 22/105:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sat 24/104:55 p.m.
YWG
-
ORD
2 stops12h 47m
Multiple Airlines
Deal found 23/7C$ 539
Thu 22/105:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sun 25/104:10 p.m.
YWG
-
ORD
2 stops19h 47m
Multiple Airlines
Deal found 23/7C$ 542
Thu 22/105:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 23/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 23/7C$ 553
Fri 21/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Tue 25/89:05 p.m.
YWG
-
ORD
2 stops34h 48m
Multiple Airlines
Deal found 19/7C$ 555
Tue 18/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 23/86:25 p.m.
YWG
-
ORD
1 stop22h 15m
WestJet
Deal found 21/7C$ 556
Fri 21/810:25 a.m.
MDW
-
YWG
1 stop9h 00m
Multiple Airlines
Tue 25/85:10 p.m.
YWG
-
MDW
1 stop16h 35m
Multiple Airlines
Deal found 19/7C$ 638

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 24 July 2026.

Round-trip from

C$ 472

One-way from

C$ 218

Popular in

January

Cheapest in

October

Average price

C$ 1,101
WestJet
  • WestJet
  • 25/9-28/9
  • 2 total stops
  • 17h 05m total
  • Illinois to Winnipeg
Search Deals
Porter Airlines
  • Porter Airlines
  • 18/9
  • 2 total stops
  • 26h 38m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 234 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 103 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 24 July 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

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 15/9

8:30 p.m.-3:19 p.m.

1 stop18h 49m

Winnipeg

Sat 19/9

9:20 a.m.-4:18 p.m.

1 stop6h 58m

C$ 821

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 18/8

11:13 a.m.-10:10 p.m.

2 stops10h 57m

Winnipeg

Mon 24/8

7:00 a.m.-4:44 p.m.

2 stops9h 44m

C$ 828

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Fri 13/11

9:45 a.m.-10:50 p.m.

2 stops13h 05m

Winnipeg

Sat 21/11

6:35 a.m.-11:18 p.m.

1 stop16h 43m

C$ 838

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 18/8

5:34 p.m.-11:30 p.m.

1 stop5h 56m

Winnipeg

Tue 25/8

9:05 p.m.-9:54 a.m.

2 stops12h 49m

C$ 838

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 28/8

7:30 p.m.-12:55 a.m.

2 stops29h 25m

Winnipeg

Mon 31/8

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

1 stop9h 40m

C$ 838

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 23/9

12:30 p.m.-9:45 a.m.

3 stops21h 15m

Winnipeg

Wed 30/9

2:55 p.m.-7:40 a.m.

2 stops16h 45m

C$ 842

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 21/10

2:50 p.m.-3:19 p.m.

1 stop24h 29m

Winnipeg

Wed 28/10

7:00 a.m.-2:20 p.m.

1 stop7h 20m

C$ 863

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 18/8

1:51 p.m.-8:40 a.m.

2 stops18h 49m

Winnipeg

Mon 24/8

4:15 p.m.-9:45 a.m.

2 stops17h 30m

C$ 895

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 2/10

1:19 p.m.-9:45 a.m.

2 stops20h 26m

Winnipeg

Sat 10/10

9:05 p.m.-2:35 p.m.

3 stops17h 30m

C$ 912

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Wed 5/8

8:48 a.m.-11:54 a.m.

1 stop27h 06m

Winnipeg

Tue 11/8

5:42 p.m.-10:23 a.m.

1 stop16h 41m

C$ 933

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/7

Showing 1-10 of 45 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 month to book a flight from Illinois to Winnipeg?

Currently, October is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 576). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,733). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 24 July 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 24 July 2026.

The most flights from USIL to YWG are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).

How much does it cost to fly round-trip from Illinois to Winnipeg?

Airfare is below average for this route at the moment.
Illinois to Winnipeg flights typically cost between C$ 1,035 and C$ 1,273 in September.
The cheapest round-trip price found within the last 5 days was C$ 472 on WestJet (25 Sep-28 Sep).

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 Porter Airlines, WestJet, and Delta fly from Illinois to Winnipeg in about 9h 51m. The time it takes to get you to your destination can typically vary by up to 8h 58m. There are 1162 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 Atlas Air (100%), Copa Airlines (79%) and SkyWest Airlines (74%).

  • 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.

  • What is the cheapest month to book a flight from Illinois to Winnipeg?

    Currently, October is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 576). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,733). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Travelling to a place near Winnipeg?

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

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