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Cheap flights from Winnipeg to Illinois from C$ 201

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 29/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
28 Feb — 7 Mar1
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 29 January 2026.

Sat 25/46:55 p.m.
YWG
-
ORD
1 stop21h 45m
WestJet
Thu 30/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 27/1C$ 349
Fri 5/67:00 a.m.
YWG
-
ORD
2 stops9h 40m
WestJet
Tue 9/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 27/1C$ 353
Fri 6/36:15 a.m.
YWG
-
ORD
1 stop7h 20m
WestJet
Mon 9/32:20 p.m.
ORD
-
YWG
1 stop8h 20m
WestJet
Deal found 27/1C$ 356
Fri 6/37:30 a.m.
YWG
-
ORD
1 stop27h 46m
Multiple Airlines
Tue 10/37:41 p.m.
ORD
-
YWG
2 stops28h 59m
Multiple Airlines
Deal found 28/1C$ 392
Thu 5/39:00 p.m.
YWG
-
ORD
1 stop16h 35m
WestJet
Mon 9/32:20 p.m.
ORD
-
YWG
1 stop8h 20m
WestJet
Deal found 27/1C$ 399
Wed 25/27:30 a.m.
YWG
-
ORD
1 stop9h 22m
Multiple Airlines
Wed 4/36:02 p.m.
ORD
-
YWG
2 stops30h 38m
Multiple Airlines
Deal found 28/1C$ 419
Sat 13/69:05 p.m.
YWG
-
ORD
1 stop19h 35m
WestJet
Tue 16/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 27/1C$ 432
Fri 6/37:30 a.m.
YWG
-
MDW
1 stop12h 17m
Multiple Airlines
Tue 10/36:00 a.m.
MDW
-
YWG
2 stops18h 40m
Multiple Airlines
Deal found 28/1C$ 434
Wed 25/27:30 a.m.
YWG
-
MDW
1 stop11h 37m
Multiple Airlines
Wed 4/37:15 a.m.
MDW
-
YWG
2 stops17h 25m
Multiple Airlines
Deal found 28/1C$ 472
Fri 6/37:30 a.m.
YWG
-
MDW
1 stop12h 17m
Multiple Airlines
Mon 9/39:51 p.m.
MDW
-
YWG
2 stops37h 41m
Multiple Airlines
Deal found 27/1C$ 487
Fri 13/37:30 a.m.
YWG
-
MDW
1 stop14h 49m
Multiple Airlines
Fri 20/311:00 a.m.
MDW
-
YWG
2 stops24h 13m
Multiple Airlines
Deal found 27/1C$ 540
Fri 13/37:30 a.m.
YWG
-
MDW
1 stop14h 49m
Multiple Airlines
Mon 30/31:10 p.m.
MDW
-
YWG
2 stops11h 29m
Multiple Airlines
Deal found 28/1C$ 555

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 29 January 2026.

Round-trip from

C$ 349

One-way from

C$ 201

Popular in

December

Cheapest in

September

Average price

C$ 648

Good round-trip deal

C$ 674 or less

Good one-way deal

C$ 257 or less
WestJet
  • WestJet
  • 25/4-30/4
  • 2 total stops
  • 29h 10m total
  • Winnipeg to Illinois
Search Deals
WestJet
  • WestJet
  • 29/5
  • 1 total stop
  • 9h 40m total
  • Winnipeg to Illinois
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 29 January 2026.
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

Sat 25/4

6:55 p.m.-4:40 p.m.

1 stop21h 45m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 349

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/6

7:00 a.m.-4:40 p.m.

2 stops9h 40m

Chicago O'Hare Intl

Tue 9/6

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 353

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 6/3

6:15 a.m.-1:35 p.m.

1 stop7h 20m

Chicago O'Hare Intl

Mon 9/3

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 356

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 25/2

7:30 a.m.-4:52 p.m.

1 stop9h 22m

Chicago O'Hare Intl

Wed 4/3

6:02 p.m.-12:40 a.m.

2 stops30h 38m

C$ 419

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 13/3

6:15 a.m.-1:35 p.m.

1 stop7h 20m

Chicago O'Hare Intl

Mon 30/3

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 419

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 13/6

9:05 p.m.-4:40 p.m.

1 stop19h 35m

Chicago O'Hare Intl

Tue 16/6

5:30 p.m.-12:55 a.m.

1 stop7h 25m

C$ 432

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 25/2

7:30 a.m.-7:07 p.m.

1 stop11h 37m

Chicago Midway

Wed 4/3

7:15 a.m.-12:40 a.m.

2 stops17h 25m

C$ 472

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 13/3

7:30 a.m.-10:19 p.m.

1 stop14h 49m

Chicago Midway

Fri 20/3

11:00 a.m.-11:13 a.m.

2 stops24h 13m

C$ 540

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

5:00 a.m.-5:45 p.m.

2 stops12h 45m

Chicago Midway

Sun 8/3

6:34 p.m.-7:09 p.m.

2 stops24h 35m

C$ 615

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 25/2

5:00 a.m.-5:37 p.m.

2 stops12h 37m

Chicago Midway

Wed 4/3

7:20 p.m.-7:09 p.m.

2 stops23h 49m

C$ 616

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/1

Showing 1-10 of 31 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.

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$ 197). Flying from Winnipeg to Illinois in January is currently the most expensive (average of C$ 699). 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 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 29 January 2026.

The most flights from YWG to USIL are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 29 January 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
9,215 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Overall

7.4

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
9,215 reviews
United Airlines
7.4
Good
9,215 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Overall

7.4

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
3,253 reviews
United Airlines
7.4
Good
9,215 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Overall

7.4

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
10,667 reviews
United Airlines
7.4
Good
9,215 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Overall

7.4

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 21h 45m. The distance between Winnipeg and Illinois is about 1136 km.

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

    Consider SkyWest Airlines (77%), Air Canada (77%) or Avianca (77%) 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$ 744, our data shows the cheapest flight currently is C$ 177. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 392 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$ 197). Flying from Winnipeg to Illinois in January is currently the most expensive (average of C$ 699). 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 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 January 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 196AverageC$ 404FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 355AverageC$ 716FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 478AverageC$ 639FlexibilityNo 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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