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Cheap flights from Winnipeg to Illinois from C$ 231

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 21/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
8 Sep — 15 Sep1
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 9 August 2026.

Wed 2/94:55 p.m. -
1 stop23h 45m
Sat 5/95:30 p.m. -
1 stop7h 25m
Deal found 7/8C$ 497
Fri 28/87:10 p.m. -
1 stop21h 30m
Mon 31/85:30 p.m. -
1 stop7h 25m
Deal found 6/8C$ 507
Tue 22/96:05 p.m. -
1 stop14h 55m
Tue 29/99:55 a.m. -
1 stop9h 54m
Deal found 8/8C$ 516
Wed 2/97:00 a.m. -
1 stop9h 40m
Thu 3/95:30 p.m. -
1 stop21h 55m
Deal found 7/8C$ 520
Thu 10/97:00 a.m. -
1 stop9h 40m
Sun 13/95:30 p.m. -
1 stop17h 40m
Deal found 8/8C$ 527
Thu 1/109:05 p.m. -
1 stop19h 35m
Thu 22/105:30 p.m. -
1 stop7h 25m
Deal found 8/8C$ 530
Mon 21/97:00 a.m. -
1 stop9h 40m
Tue 22/95:30 p.m. -
1 stop7h 25m
Deal found 4/8C$ 549
Wed 7/1011:15 a.m. -
2 stops23h 45m
Sun 11/1011:45 a.m. -
1 stop22h 00m
Deal found 4/8C$ 641
Fri 9/1011:15 a.m. -
2 stops23h 45m
Sun 11/1011:45 a.m. -
1 stop13h 10m
Deal found 4/8C$ 651
Thu 27/812:15 p.m. -
1 stop21h 30m
Mon 31/83:15 p.m. -
1 stop18h 30m
Deal found 6/8C$ 751
Fri 11/911:15 a.m. -
2 stops23h 45m
Mon 14/97:13 p.m. -
1 stop16h 38m
Deal found 8/8C$ 759
Wed 16/95:44 p.m. -
2 stops15h 23m
Sat 19/94:30 p.m. -
2 stops19h 21m
Deal found 6/8C$ 762

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 9 August 2026.

Round-trip from

C$ 497

One-way from

C$ 231

Popular in

January

Cheapest in

October

Average price

C$ 931

Good round-trip deal

C$ 697 or less

Good one-way deal

C$ 548 or less
WestJet
  • WestJet
  • 2/9-5/9
  • 2 total stops
  • 31h 10m total
  • Winnipeg to Illinois
Search Deals
21/9
  • 21/9
  • 2 total stops
  • 33h 05m total
  • Winnipeg to Illinois
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 145 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 60 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 9 August 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 Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 16/9

11:40 a.m.-8:20 p.m.

2 stops8h 40m

Chicago O'Hare Intl

Sat 19/9

8:03 a.m.-3:19 p.m.

1 stop7h 16m

C$ 723

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 7/10

9:20 a.m.-4:19 p.m.

1 stop6h 59m

Chicago O'Hare Intl

Thu 15/10

8:06 a.m.-3:19 p.m.

1 stop7h 13m

C$ 743

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Fri 28/8

12:15 p.m.-9:40 a.m.

1 stop21h 25m

Chicago Midway

Mon 31/8

3:15 p.m.-9:45 a.m.

1 stop18h 30m

C$ 773

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 14/9

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

3 stops33h 40m

Chicago O'Hare Intl

Thu 17/9

5:30 p.m.-4:40 p.m.

2 stops23h 10m

C$ 787

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Tue 22/9

12:41 p.m.-6:19 p.m.

1 stop5h 38m

Chicago Midway

Tue 29/9

9:59 a.m.-3:08 p.m.

1 stop5h 09m

C$ 807

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 1/10

5:44 p.m.-9:33 p.m.

1 stop3h 49m

Chicago O'Hare Intl

Sat 24/10

3:30 p.m.-11:19 p.m.

1 stop7h 49m

C$ 807

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Tue 13/10

9:05 p.m.-10:03 a.m.

2 stops12h 58m

Chicago Midway

Sun 18/10

1:27 p.m.-12:55 a.m.

2 stops11h 28m

C$ 824

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Wed 2/9

7:00 a.m.-6:01 p.m.

2 stops11h 01m

Chicago Midway

Thu 3/9

9:59 a.m.-9:40 p.m.

2 stops11h 41m

C$ 824

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Wed 2/9

7:00 a.m.-6:01 p.m.

2 stops11h 01m

Chicago Midway

Sat 5/9

9:24 a.m.-12:55 a.m.

2 stops15h 31m

C$ 825

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 22/8

7:00 a.m.-9:47 p.m.

2 stops14h 47m

Chicago O'Hare Intl

Mon 24/8

11:22 a.m.-12:55 a.m.

2 stops13h 33m

C$ 825

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

Showing 1-10 of 38 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, September is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of C$ 530). Flying from Winnipeg to Illinois in June is currently the most expensive (average of C$ 964). 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 9 August 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.

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

Airfare is below average for this route at the moment.
Winnipeg to Illinois flights typically cost between C$ 709 and C$ 964 in September.
The cheapest round-trip price found within the last 5 days was C$ 497 on WestJet (2 Sep-5 Sep).

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 9 August 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
10,089 reviews
Check prices

Comfort

7.3

Crew

8.1

Boarding

7.7

Food

6.7

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
10,089 reviews
United Airlines
7.4
Good
10,089 reviews
Check prices

Comfort

7.3

Crew

8.1

Boarding

7.7

Food

6.7

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,426 reviews
United Airlines
7.4
Good
10,089 reviews
Check prices

Comfort

7.3

Crew

8.1

Boarding

7.7

Food

6.7

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
11,455 reviews
United Airlines
7.4
Good
10,089 reviews
Check prices

Comfort

7.3

Crew

8.1

Boarding

7.7

Food

6.7

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 5h 38m. The distance between Winnipeg and Illinois is about 1162 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 Air Canada (84%), Air New Zealand (84%) or SkyWest Airlines (83%) 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$ 889, our data shows the cheapest flight currently is C$ 307. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 612 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, September is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of C$ 530). Flying from Winnipeg to Illinois in June is currently the most expensive (average of C$ 964). 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 9 August 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 273AverageC$ 488FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 490AverageC$ 955FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 709AverageC$ 911FlexibilityNo cancel feeOn-time67%
Search Air Canada 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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