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Cheap flights from Illinois to Winnipeg from C$ 205

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 13/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
6 Sep — 13 Sep1
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 7 August 2026.

Wed 16/92:15 p.m. -
3 stops20h 05m
Wed 23/96:05 p.m. -
1 stop14h 55m
Deal found 3/8C$ 485
Sun 20/911:05 a.m. -
2 stops13h 50m
Sun 27/96:05 p.m. -
1 stop14h 55m
Deal found 6/8C$ 527
Sun 4/105:30 p.m. -
1 stop17h 40m
Tue 6/107:00 a.m. -
1 stop9h 40m
Deal found 3/8C$ 542
Thu 3/99:50 a.m. -
1 stop15h 05m
Sun 6/99:25 a.m. -
1 stop11h 26m
Deal found 2/8C$ 551
Thu 3/93:20 p.m. -
1 stop9h 35m
Sun 6/96:05 p.m. -
1 stop16h 55m
Deal found 2/8C$ 684
Fri 4/95:23 p.m. -
2 stops22h 02m
Fri 11/99:05 p.m. -
2 stops15h 27m
Deal found 7/8C$ 832
Mon 5/1011:45 a.m. -
1 stop9h 00m
Thu 8/109:05 p.m. -
2 stops24h 53m
Deal found 6/8C$ 852
Mon 28/97:13 p.m. -
1 stop4h 17m
Wed 30/911:40 a.m. -
2 stops23h 20m
Deal found 2/8C$ 859
Thu 27/810:33 a.m. -
2 stops14h 22m
Thu 3/95:42 p.m. -
1 stop5h 44m
Deal found 3/8C$ 860
Wed 2/97:25 p.m. -
1 stop16h 29m
Wed 9/911:40 a.m. -
2 stops26h 55m
Deal found 5/8C$ 869
Mon 21/93:20 p.m. -
1 stop9h 35m
Fri 27/114:55 p.m. -
2 stops15h 07m
Deal found 6/8C$ 876
Fri 18/93:20 p.m. -
2 stops26h 38m
Fri 25/94:15 p.m. -
2 stops18h 45m
Deal found 4/8C$ 893

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 7 August 2026.

Round-trip from

C$ 485

One-way from

C$ 205

Popular in

January

Cheapest in

February

Average price

C$ 957
16/9-23/9
  • 16/9-23/9
  • 4 total stops
  • 35h 00m total
  • Illinois to Winnipeg
Search Deals
Porter Airlines
  • Porter Airlines
  • 13/9
  • 2 total stops
  • 26h 38m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 133 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 102 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 7 August 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 Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 3/9

9:50 a.m.-12:55 a.m.

1 stop15h 05m

Winnipeg

Sun 6/9

9:25 a.m.-8:51 p.m.

1 stop11h 26m

C$ 551

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 28/10

8:30 p.m.-9:57 p.m.

1 stop25h 27m

Winnipeg

Mon 2/11

7:00 a.m.-2:37 p.m.

1 stop7h 37m

C$ 792

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Fri 4/9

5:23 p.m.-3:25 p.m.

2 stops22h 02m

Winnipeg

Fri 11/9

9:05 p.m.-12:32 p.m.

2 stops15h 27m

C$ 832

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Thu 27/8

6:30 a.m.-2:25 p.m.

2 stops7h 55m

Winnipeg

Thu 3/9

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

1 stop3h 43m

C$ 863

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 23/9

11:42 a.m.-7:54 p.m.

1 stop8h 12m

Winnipeg

Sun 27/9

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

1 stop6h 58m

C$ 866

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Fri 13/11

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

2 stops13h 05m

Winnipeg

Sat 21/11

7:50 a.m.-1:26 p.m.

2 stops29h 36m

C$ 893

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Mon 21/9

12:10 p.m.-9:14 p.m.

1 stop9h 04m

Winnipeg

Wed 23/9

10:50 a.m.-6:41 p.m.

1 stop7h 51m

C$ 914

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Thu 27/8

2:40 p.m.-9:30 p.m.

1 stop6h 50m

Winnipeg

Thu 3/9

10:55 a.m.-6:42 p.m.

1 stop7h 47m

C$ 921

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Tue 29/9

12:10 p.m.-9:14 p.m.

1 stop9h 04m

Winnipeg

Thu 1/10

2:05 p.m.-8:00 p.m.

1 stop5h 55m

C$ 921

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 11/11

2:50 p.m.-9:57 p.m.

1 stop7h 07m

Winnipeg

Mon 16/11

5:00 a.m.-8:25 p.m.

2 stops15h 25m

C$ 923

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/8

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, September is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 610). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,725). 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 7 August 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 WestJet, Porter Airlines, and Delta fly from Illinois to Winnipeg in about 8h 12m. The time it takes to get you to your destination can typically vary by up to 13h 50m. 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 (75%) and SkyWest Airlines (69%).

  • 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, September is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 610). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,725). 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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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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