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Cheap flights from Winnipeg to Illinois from C$ 217

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 30/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
18 Apr — 25 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Illinois

Enter your travel dates to find the best prices.

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 19 March 2026.

Fri 8/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Fri 15/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 15/3C$ 365
Fri 5/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Tue 9/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 18/3C$ 382
Sun 3/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Thu 7/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 17/3C$ 391
Fri 22/56:00 a.m.
YWG
-
ORD
1 stop10h 40m
WestJet
Fri 29/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 14/3C$ 407
Thu 30/47:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Sun 3/55:30 p.m.
ORD
-
YWG
1 stop17h 40m
WestJet
Deal found 17/3C$ 432
Fri 8/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Mon 11/511:51 a.m.
ORD
-
YWG
2 stops27h 34m
Multiple Airlines
Deal found 15/3C$ 440
Sun 3/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Tue 5/51:59 p.m.
ORD
-
YWG
2 stops25h 26m
Multiple Airlines
Deal found 17/3C$ 441
Thu 30/47:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Sun 3/511:28 a.m.
ORD
-
YWG
2 stops27h 57m
Multiple Airlines
Deal found 17/3C$ 456
Sat 2/56:00 a.m.
YWG
-
ORD
2 stops15h 12m
Multiple Airlines
Thu 7/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Deal found 17/3C$ 463
Fri 8/59:05 p.m.
YWG
-
ORD
2 stops24h 07m
Multiple Airlines
Fri 15/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Deal found 15/3C$ 465
Thu 7/59:05 p.m.
YWG
-
ORD
1 stop19h 35m
WestJet
Sun 10/55:30 p.m.
ORD
-
YWG
1 stop18h 45m
WestJet
Deal found 17/3C$ 466
Mon 4/55:20 p.m.
YWG
-
MDW
2 stops16h 36m
Delta
Fri 8/512:53 p.m.
MDW
-
YWG
2 stops26h 02m
Delta
Deal found 17/3C$ 641

Find flight deals from Winnipeg to Illinois

Keep the following information in mind while searching for Winnipeg to Illinois flight deals. Data was last updated 19 March 2026.

Round-trip from

C$ 365

One-way from

C$ 217

Popular in

December

Cheapest in

September

Average price

C$ 811

Good round-trip deal

C$ 573 or less

Good one-way deal

C$ 339 or less
WestJet
  • WestJet
  • 8/5-15/5
  • 2 total stops
  • 17h 05m total
  • Winnipeg to Illinois
Search Deals
WestJet
  • WestJet
  • 30/4
  • 1 total stop
  • 9h 40m total
  • Winnipeg to Illinois
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 86 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Winnipeg to Illinois.
Search Deals
Price to beat on a one-way flight from Winnipeg to Illinois.
Search Deals

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 19 March 2026.
Use the filters below to find and compare flights from Winnipeg to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 18/4

6:40 a.m.-6:36 p.m.

1 stop11h 56m

Chicago Midway

Mon 20/4

7:16 p.m.-10:56 a.m.

1 stop15h 40m

C$ 691

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 1/5

5:20 p.m.-10:14 a.m.

2 stops16h 54m

Chicago Midway

Wed 6/5

7:16 p.m.-10:54 a.m.

1 stop15h 38m

C$ 700

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 24/4

5:00 a.m.-5:58 p.m.

2 stops12h 58m

Chicago Midway

Mon 27/4

9:27 a.m.-12:55 a.m.

2 stops15h 28m

C$ 710

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 18/4

6:00 a.m.-12:43 p.m.

1 stop6h 43m

Chicago O'Hare Intl

Wed 22/4

8:06 a.m.-3:30 p.m.

1 stop7h 24m

C$ 725

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 13/4

5:00 a.m.-8:47 a.m.

2 stops27h 47m

Chicago Midway

Tue 14/4

2:12 p.m.-10:56 a.m.

1 stop20h 44m

C$ 737

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 11/4

6:00 a.m.-12:43 p.m.

1 stop6h 43m

Chicago O'Hare Intl

Sat 25/4

8:06 a.m.-3:30 p.m.

1 stop7h 24m

C$ 744

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 28/4

11:55 a.m.-6:36 p.m.

1 stop6h 41m

Chicago Midway

Tue 5/5

9:29 a.m.-10:56 a.m.

1 stop25h 27m

C$ 748

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 13/4

12:20 p.m.-10:09 a.m.

2 stops21h 49m

Chicago O'Hare Intl

Thu 16/4

7:14 a.m.-7:09 p.m.

2 stops11h 55m

C$ 748

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 8/4

6:45 a.m.-6:40 p.m.

2 stops11h 55m

Chicago Midway

Mon 13/4

7:16 p.m.-11:47 p.m.

2 stops28h 31m

C$ 750

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 25/4

5:00 a.m.-5:58 p.m.

2 stops12h 58m

Chicago Midway

Mon 4/5

9:27 a.m.-12:55 a.m.

2 stops15h 28m

C$ 765

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/3

Showing 1-10 of 43 resultsSorted by cheapest first
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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.

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, May is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of C$ 199). Flying from Winnipeg to Illinois in January is currently the most expensive (average of C$ 706). 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 19 March 2026.

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 19 March 2026.

The most flights from YWG to USIL are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 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 19 March 2026.
See what other customers who have flown with United Airlines,WestJet, andAir Canada 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.
United Airlines
7.4
Good
9,439 reviews
Check prices

Overall

7.4

Food

6.6

Comfort

7.3

Entertainment

7.1

Crew

8.1

Boarding

7.7

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,439 reviews
United Airlines
7.4
Good
9,439 reviews
Check prices

Overall

7.4

Food

6.6

Comfort

7.3

Entertainment

7.1

Crew

8.1

Boarding

7.7

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
WestJet
7.2
Good
3,297 reviews
United Airlines
7.4
Good
9,439 reviews
Check prices

Overall

7.4

Food

6.6

Comfort

7.3

Entertainment

7.1

Crew

8.1

Boarding

7.7

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
Air Canada
7.1
Good
10,815 reviews
United Airlines
7.4
Good
9,439 reviews
Check prices

Overall

7.4

Food

6.6

Comfort

7.3

Entertainment

7.1

Crew

8.1

Boarding

7.7

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

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.

  • How long is the flight from Winnipeg to Illinois?

    Departing from Winnipeg to Illinois will take you 6h 43m. The distance between Winnipeg and Illinois is about 1136 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

    Consider SkyWest Airlines (75%), Air Canada (75%) or Avianca (75%) 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$ 670, our data shows the cheapest flight currently is C$ 200. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 440 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, May is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of C$ 199). Flying from Winnipeg to Illinois in January is currently the most expensive (average of C$ 706). 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 19 March 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 198AverageC$ 380FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 358AverageC$ 743FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 482AverageC$ 645FlexibilityNo 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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