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Cheap flights from Winnipeg to Illinois from C$ 208

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 20/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
4 May — 11 May1
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 April 2025.

Round-trip from

C$ 406

One-way from

C$ 208

Popular in

August

Cheapest in

June

Average price

C$ 689

Good round-trip deal

C$ 572 or less

Good one-way deal

C$ 194 or less
15/7-17/7
  • 15/7-17/7
  • 3 total stops
  • 21h 29m total
  • Winnipeg to Illinois
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20/5
  • 20/5
  • 1 total stop
  • 7h 41m total
  • Winnipeg to Illinois
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 65 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 16 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 2025.

Tue 15/79:00 a.m.YWG - ORD
1 stop7h 38mMultiple Airlines
Thu 17/76:00 a.m.ORD - YWG
2 stops13h 51mMultiple Airlines
Deal found 27/4C$ 406
Fri 5/98:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Fri 17/105:30 p.m.ORD - YWG
1 stop18h 11mWestJet
Deal found 26/4C$ 421
Thu 5/62:20 p.m.YWG - ORD
Nonstop2h 31mAir Canada
Sun 8/67:58 p.m.ORD - YWG
Nonstop2h 35mAir Canada
Deal found 27/4C$ 560
Fri 18/77:00 a.m.YWG - ORD
Nonstop2h 31mUnited Airlines
Sat 19/79:32 p.m.ORD - YWG
1 stop15h 37mUnited Airlines
Deal found 27/4C$ 575
Thu 5/66:40 a.m.YWG - ORD
2 stops9h 50mDelta
Sun 8/66:00 a.m.ORD - YWG
1 stop5h 36mDelta
Deal found 27/4C$ 588
Sat 12/76:45 a.m.YWG - MDW
2 stops14h 56mDelta
Thu 17/71:09 p.m.MDW - YWG
2 stops10h 16mDelta
Deal found 28/4C$ 596
Thu 12/68:35 a.m.YWG - MDW
1 stop9h 05mWestJet
Thu 19/69:21 a.m.MDW - YWG
1 stop7h 31mWestJet
Deal found 28/4C$ 617
Mon 9/611:45 a.m.YWG - MDW
2 stops21h 00mPorter Airlines
Tue 10/65:20 p.m.MDW - YWG
2 stops29h 26mPorter Airlines
Deal found 28/4C$ 768
Wed 30/78:15 a.m.YWG - MDW
1 stop9h 24mMultiple Airlines
Mon 4/85:20 p.m.MDW - YWG
2 stops29h 26mMultiple Airlines
Deal found 28/4C$ 784

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 April 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

Tue 15/7

9:00 a.m.-4:38 p.m.

1 stop7h 38m

Chicago O'Hare Intl

Thu 17/7

6:00 a.m.-7:51 p.m.

2 stops13h 51m

C$ 406

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 11/6

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

1 stop8h 14m

Chicago O'Hare Intl

Wed 18/6

6:00 a.m.-4:52 p.m.

1 stop10h 52m

C$ 491

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 5/6

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

Nonstop2h 31m

Chicago O'Hare Intl

Sun 8/6

7:58 p.m.-10:33 p.m.

Nonstop2h 35m

C$ 560

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 18/7

7:00 a.m.-9:31 a.m.

Nonstop2h 31m

Chicago O'Hare Intl

Sat 19/7

9:32 p.m.-1:09 p.m.

1 stop15h 37m

C$ 575

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 5/6

12:52 p.m.-9:30 p.m.

1 stop8h 38m

Chicago O'Hare Intl

Sun 8/6

6:00 a.m.-11:36 a.m.

1 stop5h 36m

C$ 588

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 12/7

6:45 a.m.-9:41 p.m.

2 stops14h 56m

Chicago Midway

Thu 17/7

1:46 p.m.-8:10 p.m.

1 stop6h 24m

C$ 596

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 12/6

8:35 a.m.-5:40 p.m.

1 stop9h 05m

Chicago Midway

Thu 19/6

9:21 a.m.-4:52 p.m.

1 stop7h 31m

C$ 617

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 9/6

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

2 stops21h 00m

Chicago Midway

Tue 10/6

5:20 p.m.-10:46 p.m.

2 stops29h 26m

C$ 768

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 30/7

8:15 a.m.-5:39 p.m.

1 stop9h 24m

Chicago Midway

Mon 4/8

5:20 p.m.-10:46 p.m.

2 stops29h 26m

C$ 784

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 20/5

9:00 a.m.-4:41 p.m.

1 stop7h 41m

C$ 208

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/4

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 29 April 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 April 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 April 2025.
Get a feel of what it's like to fly with Porter Airlines, Delta 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.
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Crew

8.8

Comfort

8.1

Overall

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Crew

8.8

Comfort

8.1

Overall

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,929 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Crew

8.8

Comfort

8.1

Overall

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,696 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Crew

8.8

Comfort

8.1

Overall

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,823 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Crew

8.8

Comfort

8.1

Overall

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Canada
7.0
Good
9,240 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Crew

8.8

Comfort

8.1

Overall

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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 Delta. According to our data, you can fly for as low as C$ 305. Users have also found prices from C$ 317 and C$ 322 on WestJet and Air Canada, respectively.

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

    Consider SkyWest Airlines (79%), Air Canada (79%) or United Airlines (79%) 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$ 632, our data shows the cheapest flight currently is C$ 156. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 345 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 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 April 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 202AverageC$ 510FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 380AverageC$ 661FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 547AverageC$ 712FlexibilityNo 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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