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Cheap flights from Illinois to Winnipeg from C$ 193

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 16/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
18 Aug — 25 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 19 July 2026.

Thu 15/105:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 18/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 17/7C$ 436
Thu 1/105:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 11/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 18/7C$ 439
Fri 2/105:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 5/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 18/7C$ 440
Thu 24/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 2/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 17/7C$ 453
Tue 1/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 11/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 17/7C$ 454
Sun 27/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Tue 6/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 18/7C$ 458
Thu 24/97:45 a.m.
ORD
-
YWG
2 stops17h 10m
Multiple Airlines
Fri 2/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 17/7C$ 464
Mon 28/97:45 a.m.
ORD
-
YWG
2 stops17h 10m
Multiple Airlines
Tue 6/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 18/7C$ 478
Fri 25/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Tue 6/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 15/7C$ 491
Fri 25/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 5/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 15/7C$ 493
Fri 16/105:30 p.m.
ORD
-
YWG
1 stop17h 40m
WestJet
Fri 23/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 15/7C$ 495
Fri 2/106:30 a.m.
ORD
-
YWG
2 stops15h 40m
Multiple Airlines
Mon 5/107:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 18/7C$ 512

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 19 July 2026.

Round-trip from

C$ 436

One-way from

C$ 193

Popular in

January

Cheapest in

October

Average price

C$ 1,096
WestJet
  • WestJet
  • 15/10-18/10
  • 2 total stops
  • 17h 05m total
  • Illinois to Winnipeg
Search Deals
WestJet
  • WestJet
  • 16/8
  • 1 total stop
  • 7h 25m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 231 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 19 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

Sat 26/9

8:03 a.m.-3:19 p.m.

1 stop7h 16m

Winnipeg

Wed 30/9

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

1 stop6h 58m

C$ 785

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

9:00 p.m.-8:12 a.m.

2 stops11h 12m

C$ 816

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sun 30/8

6:20 a.m.-3:08 p.m.

1 stop8h 48m

Winnipeg

Sun 6/9

6:40 a.m.-10:23 a.m.

1 stop3h 43m

C$ 821

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Wed 23/9

6:15 a.m.-11:56 a.m.

1 stop5h 41m

Winnipeg

Sun 27/9

5:44 p.m.-11:16 p.m.

1 stop5h 32m

C$ 850

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 1/8

5:36 p.m.-10:10 p.m.

2 stops28h 34m

Winnipeg

Thu 6/8

6:15 a.m.-9:37 a.m.

2 stops27h 22m

C$ 859

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 18/11

1:15 p.m.-9:57 p.m.

1 stop8h 42m

Winnipeg

Sun 22/11

7:00 a.m.-2:14 p.m.

1 stop7h 14m

C$ 875

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 11/11

6:10 p.m.-6:10 p.m.

2 stops24h 00m

Winnipeg

Mon 16/11

7:00 a.m.-2:14 p.m.

1 stop7h 14m

C$ 879

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 25/9

8:03 a.m.-5:58 p.m.

2 stops9h 55m

Winnipeg

Thu 1/10

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

1 stop6h 58m

C$ 893

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 4/11

1:26 p.m.-11:19 p.m.

2 stops9h 53m

Winnipeg

Sat 14/11

6:35 a.m.-11:50 p.m.

2 stops17h 15m

C$ 929

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Wed 16/9

6:15 a.m.-11:30 p.m.

1 stop17h 15m

Winnipeg

Sat 19/9

5:44 p.m.-10:31 a.m.

1 stop16h 47m

C$ 949

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/7

Showing 1-10 of 57 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$ 573). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,726). 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 19 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 19 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?

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 7h 16m. The time it takes to get you to your destination can typically vary by up to 5h 49m. There are 1136 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%).

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay C$ 578 for a flight from Illinois to Winnipeg. The cheapest flight overall is C$ 578 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at C$ 513.

  • 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$ 573). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,726). 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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