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Cheap flights from Winnipeg to Illinois from C$ 211

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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
1 Apr — 8 Apr1
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 27 March 2025.

Round-trip from

C$ 314

One-way from

C$ 211

Popular in

August

Cheapest in

June

Average price

C$ 642

Good round-trip deal

C$ 553 or less

Good one-way deal

C$ 302 or less
WestJet
  • WestJet
  • 9/6-10/6
  • 2 total stops
  • 26h 25m total
  • Winnipeg to Illinois
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WestJet
  • WestJet
  • 9/5
  • 1 total stop
  • 23h 14m total
  • Winnipeg to Illinois
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 15 potential savings vs. average RT price).
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Average for round-trip flights in March 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 27 March 2025.

Mon 9/68:30 a.m.YWG - ORD
1 stop8h 14mWestJet
Tue 10/65:30 p.m.ORD - YWG
1 stop18h 11mWestJet
Deal found 26/3C$ 314
Tue 10/68:30 a.m.YWG - ORD
1 stop8h 14mMultiple Airlines
Thu 12/65:10 a.m.ORD - YWG
1 stop11h 18mMultiple Airlines
Deal found 26/3C$ 422
Wed 24/92:15 p.m.YWG - ORD
Nonstop2h 21mUnited Airlines
Thu 25/94:00 p.m.ORD - YWG
1 stop7h 20mUnited Airlines
Deal found 26/3C$ 525
Sat 26/42:20 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Wed 7/512:57 p.m.ORD - YWG
Nonstop2h 34mAir Canada
Deal found 25/3C$ 558
Sun 8/68:35 a.m.YWG - MDW
1 stop4h 42mDelta
Tue 10/61:09 p.m.MDW - YWG
2 stops10h 20mDelta
Deal found 26/3C$ 568
Sat 26/412:32 p.m.YWG - ORD
1 stop8h 59mDelta
Wed 7/56:24 a.m.ORD - YWG
1 stop6h 10mDelta
Deal found 25/3C$ 589
Tue 10/65:42 p.m.YWG - MDW
1 stop19h 35mMultiple Airlines
Thu 12/66:00 a.m.MDW - YWG
1 stop10h 28mMultiple Airlines
Deal found 26/3C$ 609
Fri 9/511:25 a.m.YWG - MDW
2 stops21h 20mPorter Airlines
Fri 16/55:50 p.m.MDW - YWG
2 stops16h 36mPorter Airlines
Deal found 26/3C$ 646
Sun 8/66:30 a.m.YWG - MDW
2 stops12h 15mWestJet
Tue 10/61:09 p.m.MDW - YWG
2 stops10h 02mWestJet
Deal found 26/3C$ 695

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 27 March 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

Mon 9/6

8:30 a.m.-4:44 p.m.

1 stop8h 14m

Chicago O'Hare Intl

Tue 10/6

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

1 stop18h 11m

C$ 314

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 10/6

8:30 a.m.-4:44 p.m.

1 stop8h 14m

Chicago O'Hare Intl

Thu 12/6

5:10 a.m.-4:28 p.m.

1 stop11h 18m

C$ 422

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 26/4

2:20 p.m.-4:48 p.m.

Nonstop2h 28m

Chicago O'Hare Intl

Wed 7/5

12:57 p.m.-3:31 p.m.

Nonstop2h 34m

C$ 558

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 6/5

2:20 p.m.-4:48 p.m.

Nonstop2h 28m

Chicago O'Hare Intl

Wed 7/5

12:57 p.m.-3:31 p.m.

Nonstop2h 34m

C$ 559

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 8/6

8:35 a.m.-1:17 p.m.

1 stop4h 42m

Chicago Midway

Tue 10/6

1:09 p.m.-11:29 p.m.

2 stops10h 20m

C$ 568

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 26/4

12:32 p.m.-9:31 p.m.

1 stop8h 59m

Chicago O'Hare Intl

Wed 7/5

6:24 a.m.-12:34 p.m.

1 stop6h 10m

C$ 589

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 10/6

5:42 p.m.-1:17 p.m.

1 stop19h 35m

Chicago Midway

Thu 12/6

6:00 a.m.-4:28 p.m.

1 stop10h 28m

C$ 609

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 9/5

11:25 a.m.-8:45 a.m.

2 stops21h 20m

Chicago Midway

Fri 16/5

5:50 p.m.-10:26 a.m.

2 stops16h 36m

C$ 646

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 8/6

6:30 a.m.-6:45 p.m.

2 stops12h 15m

Chicago Midway

Tue 10/6

1:09 p.m.-11:11 p.m.

2 stops10h 02m

C$ 695

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/5

5:30 p.m.-4:44 p.m.

1 stop23h 14m

C$ 211

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/3

Showing 1-10 of 17 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$ 355). 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 27 March 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.

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Illinois when rainfall is around 43.0 mm.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 27 March 2025.
Get a feel of what it's like to fly with Delta, Porter Airlines and United Airlines from Winnipeg to Illinois by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,895 reviews
Check prices

Food

7.3

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,895 reviews
Delta
8.0
Very good
7,895 reviews
Check prices

Food

7.3

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Porter Airlines
7.9
Good
276 reviews
Delta
8.0
Very good
7,895 reviews
Check prices

Food

7.3

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,603 reviews
Delta
8.0
Very good
7,895 reviews
Check prices

Food

7.3

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,785 reviews
Delta
8.0
Very good
7,895 reviews
Check prices

Food

7.3

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Canada
7.0
Good
8,972 reviews
Delta
8.0
Very good
7,895 reviews
Check prices

Food

7.3

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 WestJet. According to our data, you can fly for as low as C$ 211. Users have also found prices from C$ 314 and C$ 330 on Air Canada and United Airlines, respectively.

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

    Consider SkyWest Airlines (71%), Air Canada (71%) or United Airlines (71%) 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$ 634, our data shows the cheapest flight currently is C$ 158. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 351 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$ 355). 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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Alternative routes for Winnipeg to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Winnipeg to Illinois

Discover the top 4 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 27 March 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 420AverageC$ 991FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 513AverageC$ 712FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 548AverageC$ 689FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 563AverageC$ 748FlexibilityNo 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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