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Cheap flights from Illinois to Winnipeg from C$ 113

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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
17 Oct — 24 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Illinois to Winnipeg

Keep the following information in mind while searching for Illinois to Winnipeg flight deals. Data was last updated 17 September 2025.

Round-trip from

C$ 337

One-way from

C$ 113

Popular in

February

Cheapest in

May

Average price

C$ 765

Good one-way deal

C$ 252 or less
WestJet
  • WestJet
  • 18/10-25/10
  • 2 total stops
  • 26h 24m total
  • Illinois to Winnipeg
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1/11
  • 1/11
  • 2 total stops
  • 18h 21m total
  • Illinois to Winnipeg
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Highest demand for flights based on searches. 0% potential increase in price (C$ 9 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 39 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a one-way flight from Illinois to Winnipeg.
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Find flight deals from Illinois to Winnipeg

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 17 September 2025.

Thu 9/105:30 p.m.ORD - YWG
1 stop29h 40mWestJet
Sun 12/108:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Deal found 15/9C$ 290
Fri 10/105:30 p.m.ORD - YWG
1 stop18h 11mWestJet
Sun 12/108:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Deal found 15/9C$ 296
Thu 9/102:41 p.m.ORD - YWG
2 stops25h 41mMultiple Airlines
Sun 12/108:30 a.m.YWG - ORD
1 stop8h 13mMultiple Airlines
Deal found 15/9C$ 334
Thu 16/105:30 p.m.ORD - YWG
1 stop21h 00mWestJet
Fri 24/109:05 p.m.YWG - ORD
1 stop19h 38mWestJet
Deal found 16/9C$ 356
Fri 10/105:30 p.m.ORD - YWG
1 stop18h 11mMultiple Airlines
Mon 13/109:00 a.m.YWG - ORD
1 stop6h 49mMultiple Airlines
Deal found 16/9C$ 363
Thu 30/105:50 p.m.ORD - YWG
1 stop21h 17mMultiple Airlines
Mon 3/119:00 p.m.YWG - ORD
2 stops14h 14mMultiple Airlines
Deal found 17/9C$ 374
Sun 26/102:20 p.m.ORD - YWG
1 stop19h 48mMultiple Airlines
Wed 5/117:30 a.m.YWG - ORD
2 stops17h 29mMultiple Airlines
Deal found 16/9C$ 380
Thu 30/102:20 p.m.ORD - YWG
1 stop10h 21mMultiple Airlines
Fri 31/107:30 a.m.YWG - ORD
2 stops15h 58mMultiple Airlines
Deal found 15/9C$ 384
Thu 2/1010:11 a.m.ORD - YWG
2 stops14h 02mMultiple Airlines
Mon 6/109:00 a.m.YWG - ORD
1 stop8h 16mMultiple Airlines
Deal found 15/9C$ 385
Thu 9/109:26 p.m.MDW - YWG
1 stop18h 56mMultiple Airlines
Sun 12/108:10 p.m.YWG - MDW
1 stop12h 29mMultiple Airlines
Deal found 16/9C$ 473
Sat 1/111:37 p.m.MDW - YWG
1 stop26h 30mMultiple Airlines
Sat 8/115:00 a.m.YWG - MDW
2 stops27h 52mMultiple Airlines
Deal found 17/9C$ 490
Fri 31/106:20 a.m.MDW - YWG
1 stop8h 47mMultiple Airlines
Fri 7/1112:20 p.m.YWG - MDW
2 stops33h 15mMultiple Airlines
Deal found 16/9C$ 560

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 17 September 2025.
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

Sat 18/10

5:30 p.m.-11:41 a.m.

1 stop18h 11m

Winnipeg

Sat 25/10

8:30 a.m.-4:43 p.m.

1 stop8h 13m

C$ 337

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 5/10

5:30 p.m.-9:01 a.m.

1 stop15h 31m

Winnipeg

Mon 13/10

9:00 a.m.-3:49 p.m.

1 stop6h 49m

C$ 365

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 26/10

2:20 p.m.-10:08 a.m.

1 stop19h 48m

Winnipeg

Wed 5/11

7:30 a.m.-10:35 a.m.

1 stop27h 05m

C$ 369

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 11/10

5:30 p.m.-11:26 a.m.

2 stops17h 56m

Winnipeg

Mon 13/10

9:00 a.m.-3:49 p.m.

1 stop6h 49m

C$ 374

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 16/10

5:30 p.m.-5:40 p.m.

1 stop24h 10m

Winnipeg

Fri 24/10

6:30 p.m.-4:43 p.m.

1 stop22h 13m

C$ 395

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 9/10

5:30 p.m.-11:10 p.m.

1 stop29h 40m

Winnipeg

Sun 12/10

5:00 a.m.-1:14 p.m.

1 stop8h 14m

C$ 415

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 9/10

9:26 p.m.-4:22 p.m.

1 stop18h 56m

Winnipeg

Sun 12/10

8:10 p.m.-8:39 a.m.

1 stop12h 29m

C$ 473

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 1/11

1:37 p.m.-4:07 p.m.

1 stop26h 30m

Winnipeg

Sat 8/11

5:00 a.m.-8:52 a.m.

2 stops27h 52m

C$ 490

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 31/10

6:20 a.m.-3:07 p.m.

1 stop8h 47m

Winnipeg

Fri 7/11

12:20 p.m.-9:35 p.m.

2 stops33h 15m

C$ 560

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 29/10

1:48 p.m.-11:35 a.m.

2 stops21h 47m

Winnipeg

Fri 31/10

7:30 a.m.-6:39 p.m.

1 stop11h 09m

C$ 568

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/9

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 month to book a flight from Illinois to Winnipeg?

Currently, January is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 123). Flying from Illinois to Winnipeg in July is currently the most expensive (average of C$ 232). 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 17 September 2025.

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 17 September 2025.

The most flights from USIL to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 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 Delta fly from Illinois to Winnipeg in about 12h 42m. The time it takes to get you to your destination can typically vary by up to 5h 29m. 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 (83%), Air Canada (83%) and United Airlines (83%).

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay C$ 260 for a flight from Illinois to Winnipeg. The cheapest flight overall is C$ 252 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at C$ 363.

  • 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, January is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 123). Flying from Illinois to Winnipeg in July is currently the most expensive (average of C$ 232). 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
Portage la Prairie

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Alternative routes for Illinois to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Illinois to Winnipeg

Discover the top airline that operate flights from Illinois to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 17 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 441AverageC$ 997FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Illinois to Winnipeg?

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.

Why should you use Cheapflights to find cheap flight tickets from Illinois to Winnipeg?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Winnipeg from Illinois.

Can Cheapflights find flights from Illinois to Winnipeg with no change fees?

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

Can Cheapflights notify me if prices for flights from Illinois to Winnipeg become cheaper?

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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