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$110+ Cheap flights from Illinois to Winnipeg (YWG)

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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Illinois to Winnipeg

Keep the following information in mind while searching for Illinois to Winnipeg flight deals. Data was last updated July 31, 2025.

Round-trip from

$195
(oojo)

One-way from

$123
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$641

Good round-trip deal

$448 or less

Good one-way deal

$199 or less
From Illinois to Winnipeg
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One-way flight from Illinois to Winnipeg
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Illinois to Winnipeg.
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Price to beat on a one-way flight from Illinois to Winnipeg.
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Find flight deals from Illinois to Winnipeg

Cheapest flights from Illinois to Winnipeg
Explore the most affordable flight options available from Illinois to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This oojo deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/61:40 pmORD - YWG
1 stop7h 45mWestJet
Wed 9/108:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 7/28$195
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/25:10 amORD - YWG
1 stop11h 12mMultiple Airlines
Sat 10/48:30 amYWG - ORD
1 stop8h 13mMultiple Airlines
Deal found 7/31$281
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/89:35 amMDW - YWG
2 stops13h 35mMultiple Airlines
Sun 10/126:30 amYWG - MDW
1 stop9h 54mMultiple Airlines
Deal found 7/29$375
This Gotogate deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/48:40 amORD - YWG
1 stop6h 20mAir Canada
Sun 9/77:00 amYWG - ORD
Nonstop2h 31mAir Canada
Deal found 7/31$403
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/307:15 pmMDW - YWG
1 stop4h 12mDelta
Sat 10/412:44 pmYWG - MDW
1 stop4h 51mDelta
Deal found 7/31$441
This Mytrip deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:20 pmMDW - YWG
2 stops17h 05mPorter Airlines
Sun 9/711:20 amYWG - MDW
2 stops21h 19mPorter Airlines
Deal found 7/31$478
This FlightHub deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2810:35 amMDW - YWG
1 stop28h 32mWestJet
Fri 11/77:30 amYWG - MDW
1 stop26h 10mWestJet
Deal found 7/31$565
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/176:00 amSTL - YWG
2 stops15h 30mMultiple Airlines
Sat 9/206:40 amYWG - STL
1 stop4h 50mMultiple Airlines
Deal found 7/30$643
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:35 amSTL - YWG
1 stop15h 58mUnited Airlines
Sat 9/205:00 amYWG - STL
2 stops16h 32mUnited Airlines
Deal found 7/30$648
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/179:19 amSTL - YWG
2 stops10h 52mDelta
Sat 9/206:30 amYWG - STL
2 stops12h 35mDelta
Deal found 7/30$710
This Air Canada deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/314:05 pmSTL - YWG
1 stop7h 39mAir Canada
Thu 11/67:15 amYWG - STL
1 stop8h 14mAir Canada
Deal found 7/31$813
This FlightHub deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/76:30 amSTL - YWG
1 stop5h 01mWestJet
Sun 8/106:30 amYWG - STL
2 stops11h 36mWestJet
Deal found 7/30$1,037

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Winnipeg 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 2,558,603 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.

Fly from

Illinois

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 9/6

1:40 pm-9:25 pm

1 stop7h 45m

Winnipeg

Wed 9/10

8:30 am-4:43 pm

1 stop8h 13m

$195

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/2

5:10 am-4:22 pm

1 stop11h 12m

Winnipeg

Sat 10/4

8:30 am-4:43 pm

1 stop8h 13m

$281

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 10/8

9:35 am-11:10 pm

2 stops13h 35m

Winnipeg

Sun 10/12

6:30 am-4:24 pm

1 stop9h 54m

$375

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 9/4

8:40 am-3:00 pm

1 stop6h 20m

Winnipeg

Sun 9/7

7:00 am-9:31 am

Nonstop2h 31m

$403

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 9/30

7:15 pm-11:27 pm

1 stop4h 12m

Winnipeg

Sat 10/4

12:44 pm-5:35 pm

1 stop4h 51m

$441

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 9/4

5:20 pm-10:25 am

2 stops17h 05m

Winnipeg

Sun 9/7

11:20 am-8:39 am

2 stops21h 19m

$478

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 10/28

10:35 am-3:07 pm

1 stop28h 32m

Winnipeg

Fri 11/7

7:30 am-9:40 am

1 stop26h 10m

$565

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Wed 9/17

6:00 am-9:30 pm

2 stops15h 30m

Winnipeg

Sat 9/20

6:40 am-11:30 am

1 stop4h 50m

$643

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 9/13

6:35 am-10:33 pm

1 stop15h 58m

Winnipeg

Sat 9/20

5:00 am-9:32 pm

2 stops16h 32m

$648

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Wed 9/17

9:19 am-8:11 pm

2 stops10h 52m

Winnipeg

Sat 9/20

6:30 am-7:05 pm

2 stops12h 35m

$710

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 23 results
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Best time to book a flight from Illinois to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Illinois 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 Illinois to Winnipeg

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

Currently, August is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $358). Flying from Illinois to Winnipeg in December is currently the most expensive (average of $497). 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 IL to YWG?

Find hourly flight availability from Illinois to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Winnipeg as you normally would.

Weekly flight availability from Illinois to Winnipeg

Explore weekly flight availability from Illinois to Winnipeg. 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 July 31, 2025.

The most flights from USIL to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated July 31, 2025.
Get a feel of what it's like to fly with Porter Airlines, Delta, and United Airlines from Illinois to Winnipeg by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Comfort

8.0

Crew

8.7

Boarding

8.2

Food

7.6

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Comfort

8.0

Crew

8.7

Boarding

8.2

Food

7.6

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,981 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Comfort

8.0

Crew

8.7

Boarding

8.2

Food

7.6

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,900 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Comfort

8.0

Crew

8.7

Boarding

8.2

Food

7.6

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,978 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Comfort

8.0

Crew

8.7

Boarding

8.2

Food

7.6

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,851 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Comfort

8.0

Crew

8.7

Boarding

8.2

Food

7.6

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

Related info for your journey

Find useful and relevant information for your journey from Illinois to Winnipeg. 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 into for flights to Winnipeg from Illinois?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Illinois. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • What are the cheapest airlines to fly from Illinois to Winnipeg one-way?

    $123 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on United Airlines and Air Canada, with prices starting from $183 and $188, respectively.

  • What are the most popular routes from Illinois to Winnipeg?

    While some choose either Chicago Midway - Winnipeg or Lambert-St Louis - Winnipeg, Chicago O'Hare Intl - Winnipeg is the most popular route from Illinois to Winnipeg.

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

    Consider SkyWest Airlines (81%), Air Canada (81%) or United Airlines (81%) when booking your flight. These represent the most reliable airlines when flying from Illinois to Winnipeg.

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay $655 for a flight from Illinois to Winnipeg. The cheapest flight overall is $194 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $293.

  • Can I find deals for flights from Illinois to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Illinois to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Winnipeg.

  • Can I find deals for business class flights from Illinois to Winnipeg?

    Yes. Cheapflights offers flight deals from Illinois to Winnipeg 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 Illinois to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $358). Flying from Illinois to Winnipeg in December is currently the most expensive (average of $497). 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

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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Top 2 airlines flying from Illinois to Winnipeg

Discover the top 2 airlines that operate flights from Illinois to Winnipeg. 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 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$226Average$542FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$354Average$627FlexibilityNo cancel feeOn-time69%

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