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Cheap flights from Illinois to Winnipeg from C$ 307

ORD — YWG
4 Nov — 11 Nov1
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

Tue 10/116:20 p.m. -
1 stop15h 55m
Tue 17/119:35 p.m. -
2 stops20h 55m
Deal found 5/10C$ 597
Wed 25/116:20 p.m. -
1 stop15h 55m
Mon 30/118:35 p.m. -
2 stops34h 40m
Deal found 3/10C$ 665
Tue 24/116:20 p.m. -
1 stop15h 55m
Mon 30/118:35 p.m. -
2 stops34h 40m
Deal found 3/10C$ 666
Fri 13/116:20 p.m. -
1 stop15h 55m
Mon 16/118:35 p.m. -
2 stops21h 55m
Deal found 2/10C$ 677
Thu 5/116:20 p.m. -
1 stop15h 55m
Sun 8/117:55 p.m. -
1 stop15h 45m
Deal found 4/10C$ 709
Mon 26/106:20 p.m. -
1 stop14h 55m
Wed 25/118:35 p.m. -
2 stops17h 09m
Deal found 3/10C$ 710
Mon 2/117:50 p.m. -
2 stops21h 35m
Mon 9/119:35 p.m. -
2 stops20h 55m
Deal found 5/10C$ 713
Mon 26/106:20 p.m. -
1 stop14h 55m
Thu 26/1111:00 a.m. -
1 stop24h 40m
Deal found 3/10C$ 717

Find flight deals from Illinois to Winnipeg

Round-trip from

C$ 653

One-way from

C$ 307

Popular in

August

Cheapest in

February

Average price

C$ 1,165

Good one-way deal

C$ 480 or less
22/10-27/10
  • 22/10-27/10
  • 3 total stops
  • 42h 46m total
  • Illinois to Winnipeg
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18/11-31/12
  • 18/11-31/12
  • 2 total stops
  • 20h 50m total
  • Illinois to Winnipeg
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Highest demand for flights based on searches. 13% potential increase in price (C$ 245 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease (C$ 121 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Price to beat on a one-way flight from Illinois to Winnipeg.
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Cheapflights Fare Finder

 
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

Mon 26/10

8:04 a.m.-1:10 a.m.

3 stops41h 06m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 384

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 26/10

6:20 p.m.-6:10 p.m.

2 stops23h 50m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 385

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 18/11

8:59 a.m.-4:25 p.m.

3 stops31h 26m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 402

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 15/11

8:45 p.m.-10:15 a.m.

1 stop13h 30m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 523

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 18/11

9:35 a.m.-12:23 p.m.

Nonstop2h 48m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 599

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 26/10

9:29 a.m.-12:23 p.m.

Nonstop2h 54m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 636

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 22/10

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

1 stop7h 25m

Winnipeg

Tue 27/10

9:35 p.m.-8:56 a.m.

2 stops35h 21m

C$ 653

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sat 10/10

8:06 a.m.-3:20 p.m.

1 stop7h 14m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 697

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 11/10

8:06 a.m.-3:20 p.m.

1 stop7h 14m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 709

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sat 10/10

7:54 p.m.-10:33 p.m.

Nonstop2h 39m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 757

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

Showing 1-10 of 22 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

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$ 730). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,755). 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?

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

The most flights from USIL to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

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

Airfare is typical for this route at the moment.
Illinois to Winnipeg flights typically cost between C$ 354 and C$ 1,514 in October.
The cheapest round-trip price found within the last 5 days was C$ 653 on Multiple Airlines (22 Oct-27 Oct).

Related info for your journey

  • 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 fly from Illinois to Winnipeg in about 23h 50m. The time it takes to get you to your destination can typically vary by up to . There are 1136 km between Illinois and Winnipeg.

  • 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 (74%), United Airlines (74%) and Air Canada (69%).

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay C$ 563 for a flight from Illinois to Winnipeg. The cheapest flight overall is C$ 480 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at C$ 707.

  • 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$ 730). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,755). 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

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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.

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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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