Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Winnipeg to Illinois from C$ 182

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 26/11. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

Find 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 October 2025.

Fri 5/127:30 a.m.YWG - ORD
1 stop28h 24mMultiple Airlines
Sun 7/1210:24 a.m.ORD - YWG
2 stops14h 17mMultiple Airlines
Deal found 29/10C$ 276
Wed 26/117:30 a.m.YWG - ORD
1 stop16h 38mMultiple Airlines
Wed 3/128:00 a.m.ORD - YWG
2 stops16h 41mMultiple Airlines
Deal found 29/10C$ 297
Thu 4/129:00 p.m.YWG - MDW
2 stops25h 12mMultiple Airlines
Sun 7/126:15 a.m.MDW - YWG
1 stop8h 52mMultiple Airlines
Deal found 29/10C$ 299
Tue 11/119:00 p.m.YWG - MDW
2 stops15h 41mMultiple Airlines
Tue 18/111:56 p.m.MDW - YWG
1 stop25h 11mMultiple Airlines
Deal found 29/10C$ 300
Tue 11/119:00 p.m.YWG - ORD
2 stops14h 14mMultiple Airlines
Tue 18/1112:37 p.m.ORD - YWG
1 stop26h 30mMultiple Airlines
Deal found 29/10C$ 300
Thu 4/129:00 p.m.YWG - ORD
2 stops17h 40mMultiple Airlines
Sun 7/126:11 a.m.ORD - YWG
1 stop8h 56mMultiple Airlines
Deal found 29/10C$ 341
Fri 5/127:30 a.m.YWG - ORD
1 stop28h 24mMultiple Airlines
Mon 8/129:27 p.m.ORD - YWG
2 stops27h 12mMultiple Airlines
Deal found 28/10C$ 350
Sat 15/119:00 p.m.YWG - ORD
2 stops27h 11mMultiple Airlines
Sat 13/121:24 p.m.ORD - YWG
1 stop25h 43mMultiple Airlines
Deal found 28/10C$ 371
Fri 28/117:30 a.m.YWG - MDW
1 stop7h 10mMultiple Airlines
Fri 5/128:42 p.m.MDW - YWG
2 stops27h 59mMultiple Airlines
Deal found 29/10C$ 383
Fri 21/117:30 a.m.YWG - MDW
1 stop7h 10mMultiple Airlines
Tue 25/116:05 a.m.MDW - YWG
2 stops18h 36mMultiple Airlines
Deal found 29/10C$ 398
Fri 21/117:30 a.m.YWG - MDW
1 stop7h 10mMultiple Airlines
Sun 23/116:05 a.m.MDW - YWG
1 stop9h 02mMultiple Airlines
Deal found 30/10C$ 465
Wed 26/117:30 a.m.YWG - MDW
1 stop15h 13mMultiple Airlines
Wed 3/1211:00 a.m.MDW - YWG
1 stop13h 42mMultiple Airlines
Deal found 29/10C$ 503

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 30 October 2025.

Round-trip from

C$ 276

One-way from

C$ 182

Popular in

April

Cheapest in

September

Average price

C$ 521

Good round-trip deal

C$ 613 or less

Good one-way deal

C$ 282 or less
5/12-7/12
  • 5/12-7/12
  • 3 total stops
  • 42h 41m total
  • Winnipeg to Illinois
Search Deals
26/11
  • 26/11
  • 1 total stop
  • 15h 13m total
  • Winnipeg to Illinois
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 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

Fri 5/12

7:30 a.m.-11:54 a.m.

1 stop28h 24m

Chicago O'Hare Intl

Sun 7/12

6:11 a.m.-3:07 p.m.

1 stop8h 56m

C$ 282

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 26/11

7:30 a.m.-12:08 a.m.

1 stop16h 38m

Chicago O'Hare Intl

Wed 3/12

8:00 a.m.-12:41 a.m.

2 stops16h 41m

C$ 297

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 4/12

9:00 p.m.-10:12 p.m.

2 stops25h 12m

Chicago Midway

Sun 7/12

6:15 a.m.-3:07 p.m.

1 stop8h 52m

C$ 299

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 11/11

9:00 p.m.-12:41 p.m.

2 stops15h 41m

Chicago Midway

Tue 18/11

1:56 p.m.-3:07 p.m.

1 stop25h 11m

C$ 332

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/12

7:30 a.m.-11:54 a.m.

1 stop28h 24m

Chicago O'Hare Intl

Mon 8/12

7:10 a.m.-6:03 p.m.

1 stop10h 53m

C$ 369

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 28/11

7:30 a.m.-2:40 p.m.

1 stop7h 10m

Chicago Midway

Fri 5/12

8:42 p.m.-12:41 a.m.

2 stops27h 59m

C$ 383

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 21/11

7:30 a.m.-2:40 p.m.

1 stop7h 10m

Chicago Midway

Tue 25/11

6:05 a.m.-12:41 a.m.

2 stops18h 36m

C$ 398

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 21/11

7:30 a.m.-12:08 a.m.

1 stop16h 38m

Chicago O'Hare Intl

Tue 25/11

11:48 a.m.-3:07 p.m.

2 stops27h 19m

C$ 447

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 11/11

9:00 p.m.-8:27 p.m.

3 stops23h 27m

Chicago O'Hare Intl

Thu 13/11

10:52 a.m.-8:06 p.m.

3 stops33h 14m

C$ 473

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 12/12

7:30 a.m.-11:54 a.m.

1 stop28h 24m

Chicago O'Hare Intl

Fri 19/12

1:27 p.m.-1:23 a.m.

1 stop11h 56m

C$ 489

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/10

Showing 1-10 of 33 results
1
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

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$ 202). Flying from Winnipeg to Illinois in March is currently the most expensive (average of C$ 554). 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 October 2025.

A simple way to save on the total cost of your ticket is to fly from Winnipeg to Illinois in the evening. If you’re flexible enough to do this you can expect to save up to 47% on your trip compared to booking a flight in the morning.

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 October 2025.
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
8,998 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

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
8,998 reviews
United Airlines
7.4
Good
8,998 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

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
3,152 reviews
United Airlines
7.4
Good
8,998 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

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
10,381 reviews
United Airlines
7.4
Good
8,998 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

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.

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

    Consider SkyWest Airlines (85%), Air Canada (85%) or United Airlines (85%) 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$ 893, our data shows the cheapest flight currently is C$ 196. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 257 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$ 202). Flying from Winnipeg to Illinois in March is currently the most expensive (average of C$ 554). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Winnipeg to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Orlando flights
Winnipeg to Las Vegas flights
Winnipeg to Sky Harbor Intl flights
Winnipeg to Fort Lauderdale flights
Winnipeg to Palm Springs flights
Winnipeg to Miami flights
Winnipeg to O'Hare Intl flights
Winnipeg to John F Kennedy Intl flights
Winnipeg to Minneapolis flights
Winnipeg to Los Angeles flights
Winnipeg to Newark flights
Winnipeg to LaGuardia flights
Winnipeg to Atlanta flights
Winnipeg to San Francisco flights
Winnipeg to Hobby flights
Winnipeg to George Bush Intcntl flights
Winnipeg to Nashville flights
Winnipeg to Ontario flights
Winnipeg to Honolulu flights
Winnipeg to Dallas/Fort Worth flights
Winnipeg to Denver flights
Winnipeg to Reagan-National flights
Winnipeg to Tampa flights
Winnipeg to Dulles Intl flights
Winnipeg to San Diego flights
Winnipeg to New Orleans flights
Winnipeg to Portland flights
Winnipeg to Seattle flights
Winnipeg to Detroit flights
Winnipeg to Austin flights
Winnipeg to Kahului flights
Winnipeg to Baltimore flights
Winnipeg to Love Field flights
Winnipeg to Fort Myers flights
Winnipeg to Santa Ana flights
Winnipeg to Indianapolis flights
Winnipeg to Boston flights
Brandon to Las Vegas flights
Winnipeg to Buffalo flights
Winnipeg to Philadelphia flights
Winnipeg to Sacramento flights
Winnipeg to Charleston flights
Winnipeg to San Antonio flights
Winnipeg to Charlotte flights
Winnipeg to Daytona Beach flights
Winnipeg to Memphis flights
Winnipeg to Des Moines flights
Winnipeg to Kansas City flights
Winnipeg to Tulsa flights

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 October 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 202AverageC$ 463FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 365AverageC$ 635FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 491AverageC$ 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.