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Cheap flights from Winnipeg to Illinois from C$ 164

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 25/2. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
3 Feb — 10 Feb1
1 adult

Cheap flight deals from Winnipeg to Illinois

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Illinois (USIL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 29 January 2025.

Round-trip from

C$ 409

One-way from

C$ 164

Popular in

August

Cheapest in

June

Average price

C$ 754

Good round-trip deal

C$ 595 or less

Good one-way deal

C$ 327 or less
2/3-5/3
  • 2/3-5/3
  • 5 total stops
  • 51h 57m total
  • Winnipeg to Illinois
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25/2
  • 25/2
  • 1 total stop
  • 9h 01m total
  • Winnipeg to Illinois
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Highest demand for flights based on searches. 6% potential increase in price (C$ 62 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 14 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 2025.

Sun 2/36:25 p.m.YWG - ORD
3 stops35h 03mMultiple Airlines
Wed 5/37:47 a.m.ORD - YWG
2 stops16h 54mMultiple Airlines
Deal found 28/1C$ 409
Sat 20/98:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Sun 21/95:30 p.m.ORD - YWG
1 stop18h 11mWestJet
Deal found 28/1C$ 419
Sat 20/94:15 p.m.YWG - ORD
1 stop6h 10mUnited Airlines
Sun 21/97:30 a.m.ORD - YWG
2 stops15h 50mUnited Airlines
Deal found 28/1C$ 475
Sun 2/38:00 p.m.YWG - MDW
1 stop14h 20mMultiple Airlines
Wed 5/311:15 a.m.MDW - YWG
1 stop12h 40mMultiple Airlines
Deal found 28/1C$ 491
Sun 2/37:30 a.m.YWG - ORD
1 stop5h 41mAir Canada
Wed 5/39:50 a.m.ORD - YWG
1 stop7h 28mAir Canada
Deal found 28/1C$ 536
Wed 9/46:50 a.m.YWG - ORD
2 stops11h 29mDelta
Tue 22/46:40 a.m.ORD - YWG
1 stop4h 54mDelta
Deal found 29/1C$ 636
Wed 26/312:53 p.m.YWG - MDW
1 stop5h 25mDelta
Wed 2/41:16 p.m.MDW - YWG
1 stop6h 59mDelta
Deal found 29/1C$ 644
Fri 28/25:37 p.m.YWG - MDW
1 stop24h 06mWestJet
Tue 4/310:19 a.m.MDW - YWG
1 stop25h 32mWestJet
Deal found 28/1C$ 681
Tue 18/211:35 a.m.YWG - MDW
2 stops24h 35mPorter Airlines
Tue 4/311:15 a.m.MDW - YWG
2 stops30h 44mPorter Airlines
Deal found 28/1C$ 806

Find flights from Winnipeg to Illinois within your budget

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 January 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 2/3

6:25 p.m.-5:28 a.m.

3 stops35h 03m

Chicago O'Hare Intl

Wed 5/3

7:47 a.m.-12:41 a.m.

2 stops16h 54m

C$ 409

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 27/2

8:15 a.m.-3:56 p.m.

1 stop7h 41m

Chicago O'Hare Intl

Sun 2/3

4:45 p.m.-7:35 p.m.

1 stop26h 50m

C$ 429

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 2/3

8:00 p.m.-10:20 a.m.

1 stop14h 20m

Chicago Midway

Wed 5/3

11:15 a.m.-11:55 p.m.

1 stop12h 40m

C$ 491

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 2/3

7:30 a.m.-1:11 p.m.

1 stop5h 41m

Chicago O'Hare Intl

Wed 5/3

9:50 a.m.-5:18 p.m.

1 stop7h 28m

C$ 536

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 9/4

6:50 a.m.-6:19 p.m.

2 stops11h 29m

Chicago O'Hare Intl

Tue 22/4

6:40 a.m.-11:34 a.m.

1 stop4h 54m

C$ 636

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 20/3

2:15 p.m.-4:37 p.m.

Nonstop2h 22m

Chicago O'Hare Intl

Mon 24/3

12:58 p.m.-3:28 p.m.

Nonstop2h 30m

C$ 638

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 26/3

12:53 p.m.-6:18 p.m.

1 stop5h 25m

Chicago Midway

Tue 1/4

1:16 p.m.-8:15 p.m.

1 stop6h 59m

C$ 644

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 28/2

5:37 p.m.-5:43 p.m.

1 stop24h 06m

Chicago Midway

Tue 4/3

10:19 a.m.-11:51 a.m.

1 stop25h 32m

C$ 681

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 18/2

11:35 a.m.-12:10 p.m.

2 stops24h 35m

Chicago Midway

Tue 4/3

11:15 a.m.-5:59 p.m.

2 stops30h 44m

C$ 806

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 25/2

7:30 a.m.-4:31 p.m.

1 stop9h 01m

C$ 164

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/1

Showing 1-10 of 18 results
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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.

Travel insights for flights from Winnipeg to Illinois

Get recent, data-driven insights about flights from Winnipeg to Illinois including ideal travel times, pricing trends, and more.

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 29 January 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 January 2025.

The most flights from YWG to USIL are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

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 29 January 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
8,456 reviews
Check prices

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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
8,456 reviews
Delta
8.0
Very good
8,456 reviews
Check prices

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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
278 reviews
Delta
8.0
Very good
8,456 reviews
Check prices

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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
8,922 reviews
Delta
8.0
Very good
8,456 reviews
Check prices

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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
2,819 reviews
Delta
8.0
Very good
8,456 reviews
Check prices

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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
8,636 reviews
Delta
8.0
Very good
8,456 reviews
Check prices

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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$ 203. Users have also found prices from C$ 285 and C$ 344 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$ 660, our data shows the cheapest flight currently is C$ 190. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 406 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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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 29 January 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 396AverageC$ 720FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 499AverageC$ 673FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
WestJetCheapestC$ 503AverageC$ 840FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 568AverageC$ 754FlexibilityNo 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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