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Cheap flights from Winnipeg to Illinois from C$ 222

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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
3 Aug — 10 Aug1
1 adult

Cheap flight deals from Winnipeg to Illinois

Keep the following information in mind while searching for Winnipeg to Illinois flight deals. Data was last updated 29 July 2025.

Round-trip from

C$ 305

One-way from

C$ 222

Popular in

April

Cheapest in

June

Average price

C$ 616

Good round-trip deal

C$ 724 or less

Good one-way deal

C$ 406 or less
WestJet
  • WestJet
  • 18/9-23/9
  • 2 total stops
  • 32h 23m total
  • Winnipeg to Illinois
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2/9
  • 2/9
  • 1 total stop
  • 19h 48m total
  • Winnipeg to Illinois
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Highest demand for flights based on searches. 3% potential increase in price (C$ 28 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 13 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Winnipeg to Illinois.
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Price to beat on a one-way flight from Winnipeg to Illinois.
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Find flight deals from Winnipeg to Illinois

Cheapest flights from Winnipeg to Illinois
Explore the most affordable flight options available from Winnipeg to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 29 July 2025.

Thu 18/98:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Tue 23/95:30 p.m.ORD - YWG
1 stop24h 10mWestJet
Deal found 27/7C$ 305
Fri 5/98:30 a.m.YWG - ORD
1 stop8h 13mMultiple Airlines
Mon 8/912:53 p.m.ORD - YWG
2 stops11h 20mMultiple Airlines
Deal found 26/7C$ 342
Fri 5/96:30 a.m.YWG - MDW
1 stop9h 54mMultiple Airlines
Fri 12/96:20 a.m.MDW - YWG
1 stop10h 02mMultiple Airlines
Deal found 27/7C$ 421
Fri 12/912:00 p.m.YWG - ORD
1 stop8h 11mAir Canada
Fri 19/910:40 a.m.ORD - YWG
1 stop8h 19mAir Canada
Deal found 29/7C$ 444
Wed 10/92:20 p.m.YWG - ORD
Nonstop2h 31mUnited Airlines
Wed 17/97:54 p.m.ORD - YWG
Nonstop2h 39mUnited Airlines
Deal found 27/7C$ 464
Wed 10/96:40 a.m.YWG - MDW
1 stop6h 23mDelta
Wed 17/99:20 a.m.MDW - YWG
1 stop7h 30mDelta
Deal found 27/7C$ 524
Fri 19/95:40 p.m.YWG - MDW
1 stop23h 55mWestJet
Tue 23/99:20 a.m.MDW - YWG
1 stop26h 34mWestJet
Deal found 27/7C$ 583
Fri 31/104:25 p.m.YWG - MDW
2 stops17h 40mPorter Airlines
Mon 3/114:15 p.m.MDW - YWG
2 stops18h 58mPorter Airlines
Deal found 28/7C$ 776

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Illinois 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 29 July 2025.
Use the filters below to find and compare flights from Winnipeg to Illinois that are best for you.

Fly from

Winnipeg

Fly to

Illinois

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 18/9

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

1 stop8h 13m

Chicago O'Hare Intl

Tue 23/9

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

1 stop24h 10m

C$ 305

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/9

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

1 stop8h 13m

Chicago O'Hare Intl

Mon 8/9

12:53 p.m.-12:13 a.m.

2 stops11h 20m

C$ 342

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 5/9

6:30 a.m.-4:24 p.m.

1 stop9h 54m

Chicago Midway

Fri 12/9

6:20 a.m.-4:22 p.m.

1 stop10h 02m

C$ 421

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 12/9

12:00 p.m.-8:11 p.m.

1 stop8h 11m

Chicago O'Hare Intl

Fri 19/9

10:40 a.m.-6:59 p.m.

1 stop8h 19m

C$ 444

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 10/9

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

Chicago O'Hare Intl

Wed 17/9

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

Nonstop2h 39m

C$ 464

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 10/9

6:40 a.m.-1:03 p.m.

1 stop6h 23m

Chicago Midway

Wed 17/9

9:20 a.m.-4:50 p.m.

1 stop7h 30m

C$ 524

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 19/9

5:40 p.m.-5:35 p.m.

1 stop23h 55m

Chicago Midway

Tue 23/9

9:20 a.m.-11:54 a.m.

1 stop26h 34m

C$ 583

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 31/10

4:25 p.m.-10:05 a.m.

2 stops17h 40m

Chicago Midway

Mon 3/11

4:15 p.m.-11:13 a.m.

2 stops18h 58m

C$ 776

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 2/9

8:55 p.m.-4:43 p.m.

1 stop19h 48m

C$ 222

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 20/9

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

C$ 277

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/7

Showing 1-10 of 16 results
1
2

Best time to book a flight from Winnipeg to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Winnipeg 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 Winnipeg to Illinois

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

Currently, January is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of C$ 261). Flying from Winnipeg to Illinois in March is currently the most expensive (average of C$ 352). 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 YWG to IL?

Find hourly flight availability from Winnipeg to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 29 July 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Illinois as you normally would.

Weekly flight availability from Winnipeg to Illinois

Explore weekly flight availability from Winnipeg to Illinois. 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 29 July 2025.

The most flights from YWG to USIL are scheduled on a Monday (8 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (6 on average).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated 29 July 2025.
See what other customers who have flown with Porter Airlines,Delta, andUnited Airlines from Winnipeg to Illinois have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
317 reviews
Check prices

Overall

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
317 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Overall

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,979 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Overall

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,896 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Overall

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,972 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Overall

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,826 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Overall

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Illinois. 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 from for flights from Winnipeg to Illinois?

    If you book a flight to Illinois from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg.

  • What are the cheapest airlines to fly from Winnipeg to Illinois one-way?

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as C$ 277. Users have also found prices from C$ 285 and C$ 320 on Delta and Air Canada, respectively.

  • What are the most reliable airlines from Winnipeg to Illinois?

    Consider Avianca (93%), SkyWest Airlines (91%) or United Airlines (91%) when booking your flight. These represent the most reliable airlines when flying from Winnipeg to Illinois.

  • What are the cheapest flights from Winnipeg to Illinois?

    While on average a flight from Winnipeg to Illinois is generally C$ 1,116, our data shows the cheapest flight currently is C$ 244. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 336 for that flight.

  • Can I find deals for flights from Winnipeg to Illinois that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Illinois.

  • Can I find deals for business class flights from Winnipeg to Illinois?

    Yes. Cheapflights offers flight deals from Winnipeg to Illinois 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 Winnipeg to Illinois?

    Currently, January is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of C$ 261). Flying from Winnipeg to Illinois in March is currently the most expensive (average of C$ 352). 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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Top 3 airlines flying from Winnipeg to Illinois

Discover the top 3 airlines that operate flights from Winnipeg to Illinois. 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 29 July 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 198AverageC$ 408FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 376AverageC$ 591FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 508AverageC$ 679FlexibilityNo cancel feeOn-time69%
Search United Airlines 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 Winnipeg to Illinois?

Cheapflights helps you search for flights from Winnipeg to Illinois via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

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

Cheapflights helps you find that perfect flight to Illinois from Winnipeg by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

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

Certainly. Search results for flights to Illinois from Winnipeg shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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

Of course! You can now track prices for flights from Winnipeg to Illinois and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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