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Cheap flights from Winnipeg to Illinois from C$ 254

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 31/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
30 May — 6 Jun1
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 30 April 2026.

Thu 28/59:05 p.m.
YWG
-
ORD
1 stop19h 35m
WestJet
Thu 4/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 28/4C$ 365
Wed 10/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Mon 15/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 29/4C$ 375
Tue 15/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Fri 18/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 29/4C$ 386
Fri 21/87:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Mon 24/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 25/4C$ 431
Tue 26/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Tue 2/69:37 p.m.
ORD
-
YWG
2 stops22h 38m
Multiple Airlines
Deal found 26/4C$ 460
Fri 21/87:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Sun 23/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 25/4C$ 462
Thu 20/87:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Sat 22/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 25/4C$ 475
Sat 22/87:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Mon 24/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 25/4C$ 497
Fri 29/56:00 a.m.
YWG
-
ORD
1 stop10h 40m
Multiple Airlines
Tue 2/69:37 p.m.
ORD
-
YWG
2 stops22h 38m
Multiple Airlines
Deal found 26/4C$ 505
Thu 28/59:05 p.m.
YWG
-
MDW
2 stops14h 04m
Multiple Airlines
Thu 4/63:20 p.m.
MDW
-
YWG
1 stop18h 25m
Multiple Airlines
Deal found 28/4C$ 535
Thu 20/88:45 p.m.
YWG
-
MDW
1 stop12h 55m
Multiple Airlines
Tue 25/86:00 a.m.
MDW
-
YWG
2 stops16h 10m
Multiple Airlines
Deal found 25/4C$ 571
Thu 28/58:45 p.m.
YWG
-
MDW
1 stop17h 50m
Porter Airlines
Thu 4/610:15 a.m.
MDW
-
YWG
1 stop9h 34m
Porter Airlines
Deal found 28/4C$ 628

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 30 April 2026.

Round-trip from

C$ 365

One-way from

C$ 254

Popular in

March

Cheapest in

October

Average price

C$ 691

Good round-trip deal

C$ 589 or less

Good one-way deal

C$ 398 or less
WestJet
  • WestJet
  • 28/5-4/6
  • 2 total stops
  • 27h 00m total
  • Winnipeg to Illinois
Search Deals
WestJet
  • WestJet
  • 31/8
  • 1 total stop
  • 9h 40m total
  • Winnipeg to Illinois
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 154 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 30 April 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 23/5

6:40 a.m.-9:09 p.m.

2 stops14h 29m

Chicago Midway

Wed 27/5

5:12 p.m.-2:55 p.m.

2 stops21h 43m

C$ 640

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 23/6

5:41 p.m.-9:14 a.m.

2 stops15h 33m

Chicago Midway

Tue 30/6

6:58 p.m.-3:04 p.m.

2 stops20h 06m

C$ 694

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 16/6

6:40 a.m.-10:17 p.m.

2 stops15h 37m

Chicago Midway

Sat 20/6

6:00 a.m.-11:29 p.m.

2 stops17h 29m

C$ 707

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 21/7

7:00 a.m.-9:08 a.m.

2 stops26h 08m

Chicago Midway

Thu 23/7

9:20 a.m.-12:55 a.m.

2 stops15h 35m

C$ 739

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 4/6

4:15 p.m.-9:35 a.m.

2 stops17h 20m

Chicago Midway

Sun 7/6

10:15 a.m.-5:58 p.m.

2 stops7h 43m

C$ 740

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 23/6

12:46 p.m.-6:18 p.m.

1 stop5h 32m

Chicago Midway

Tue 30/6

1:49 p.m.-4:51 p.m.

1 stop27h 02m

C$ 759

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 20/6

7:00 a.m.-6:02 a.m.

3 stops23h 02m

Chicago O'Hare Intl

Sun 28/6

5:30 p.m.-3:25 p.m.

1 stop21h 55m

C$ 761

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 16/6

9:20 a.m.-4:18 p.m.

1 stop6h 58m

Chicago O'Hare Intl

Sat 20/6

8:08 a.m.-3:19 p.m.

1 stop7h 11m

C$ 761

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 23/6

5:41 p.m.-9:25 p.m.

1 stop3h 44m

Chicago O'Hare Intl

Tue 30/6

6:30 a.m.-11:56 a.m.

1 stop5h 26m

C$ 814

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 23/9

6:40 a.m.-2:58 p.m.

1 stop8h 18m

Chicago O'Hare Intl

Sat 26/9

5:20 p.m.-11:27 p.m.

1 stop6h 07m

C$ 837

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/4

Showing 1-10 of 36 resultsSorted by cheapest first
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2
3
4

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

How far ahead should I book a flight from Winnipeg to Illinois?

To ensure you get the cheapest price possible for a flight from Winnipeg to Illinois, you should look to book at least 77 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, October is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of C$ 109). Flying from Winnipeg to Illinois in January is currently the most expensive (average of C$ 609). 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 30 April 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 30 April 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).

How much does it cost to fly round-trip from Winnipeg to Illinois?

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 30 April 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
9,677 reviews
Check prices

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Food

6.6

Entertainment

7.1

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
9,677 reviews
United Airlines
7.4
Good
9,677 reviews
Check prices

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Food

6.6

Entertainment

7.1

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
3,328 reviews
United Airlines
7.4
Good
9,677 reviews
Check prices

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Food

6.6

Entertainment

7.1

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
10,982 reviews
United Airlines
7.4
Good
9,677 reviews
Check prices

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Food

6.6

Entertainment

7.1

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 3h 44m. 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 Avianca (71%), SkyWest Airlines (71%) or Air Canada (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$ 604, our data shows the cheapest flight currently is C$ 288. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 514 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, October is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of C$ 109). Flying from Winnipeg to Illinois in January is currently the most expensive (average of C$ 609). 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 30 April 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 268AverageC$ 386FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 361AverageC$ 742FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 477AverageC$ 636FlexibilityNo 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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