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Illinois

$160+ Cheap flights from Winnipeg (YWG) to Illinois

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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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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 July 31, 2025.

Round-trip from

$212
(Kiwi.com)

One-way from

$160
(Kiwi.com)

Popular in

April

Cheapest in

June

Average price

$449

Good round-trip deal

$385 or less

Good one-way deal

$361 or less
From Winnipeg to Illinois
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One-way flight from Winnipeg to Illinois
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Highest demand for flights based on searches. 3% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 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 Winnipeg to Illinois.
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Price to beat on a one-way flight from Winnipeg to Illinois.
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Find flight deals from Winnipeg to Illinois

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 July 31, 2025.

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 9/248:30 amYWG - ORD
1 stop8h 13mWestJet
Sat 9/271:40 pmORD - YWG
1 stop7h 45mWestJet
Deal found 7/30$212
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/137:00 pmYWG - ORD
2 stops14h 51mMultiple Airlines
Sat 9/201:40 pmORD - YWG
1 stop7h 45mMultiple Airlines
Deal found 7/30$293
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1212:00 pmYWG - ORD
1 stop8h 11mAir Canada
Fri 9/1910:40 amORD - YWG
1 stop8h 19mAir Canada
Deal found 7/29$324
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/182:20 pmYWG - ORD
Nonstop2h 31mUnited Airlines
Sun 9/211:01 pmORD - YWG
Nonstop2h 30mUnited Airlines
Deal found 7/31$336
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.
Sat 9/136:40 amYWG - MDW
2 stops5h 48mDelta
Sat 9/201:08 pmMDW - YWG
2 stops10h 19mDelta
Deal found 7/30$359
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/199:05 pmYWG - MDW
2 stops12h 31mWestJet
Wed 8/2012:43 pmMDW - YWG
2 stops11h 48mWestJet
Deal found 7/29$436
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:55 pmYWG - MDW
1 stop13h 50mMultiple Airlines
Wed 9/35:20 pmMDW - YWG
1 stop16h 21mMultiple Airlines
Deal found 7/30$485
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1611:20 amYWG - MDW
2 stops29h 04mPorter Airlines
Sun 10/195:20 pmMDW - YWG
2 stops17h 05mPorter Airlines
Deal found 7/28$587
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.
Thu 10/97:00 amYWG - STL
1 stop8h 44mUnited Airlines
Mon 10/135:28 pmSTL - YWG
2 stops19h 41mUnited Airlines
Deal found 7/30$588
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.
Fri 11/215:38 pmYWG - STL
1 stop5h 24mDelta
Mon 11/246:30 amSTL - YWG
1 stop5h 08mDelta
Deal found 7/30$625
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2110:55 amYWG - STL
2 stops12h 07mWestJet
Thu 11/276:30 amSTL - YWG
2 stops11h 36mWestJet
Deal found 7/31$638

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 2,558,603 searches. Data last updated July 31, 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

Wed 9/24

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sat 9/27

1:40 pm-9:25 pm

1 stop7h 45m

$212

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 9/13

7:00 pm-9:51 am

2 stops14h 51m

Chicago O'Hare Intl

Sat 9/20

1:40 pm-9:25 pm

1 stop7h 45m

$293

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/12

12:00 pm-8:11 pm

1 stop8h 11m

Chicago O'Hare Intl

Fri 9/19

10:40 am-6:59 pm

1 stop8h 19m

$324

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/18

2:20 pm-4:51 pm

Nonstop2h 31m

Chicago O'Hare Intl

Sun 9/21

1:01 pm-3:31 pm

Nonstop2h 30m

$336

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 9/13

6:40 am-12:28 pm

2 stops5h 48m

Chicago Midway

Sat 9/20

1:08 pm-11:27 pm

2 stops10h 19m

$359

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 8/19

9:05 pm-9:36 am

2 stops12h 31m

Chicago Midway

Wed 8/20

12:43 pm-12:31 am

2 stops11h 48m

$436

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 8/27

6:55 pm-8:45 am

1 stop13h 50m

Chicago Midway

Wed 9/3

5:20 pm-9:41 am

1 stop16h 21m

$485

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/16

11:20 am-4:24 pm

2 stops29h 04m

Chicago Midway

Sun 10/19

5:20 pm-10:25 am

2 stops17h 05m

$587

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Thu 10/9

7:00 am-3:44 pm

1 stop8h 44m

Lambert-St Louis

Mon 10/13

5:28 pm-1:09 pm

2 stops19h 41m

$588

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Fri 11/21

5:38 pm-11:02 pm

1 stop5h 24m

Lambert-St Louis

Mon 11/24

6:30 am-11:38 am

1 stop5h 08m

$625

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 22 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, August is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of $245). Flying from Winnipeg to Illinois in March is currently the most expensive (average of $321). 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 July 31, 2025.

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 July 31, 2025.

The most flights from YWG to USIL are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 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 July 31, 2025.
Get a feel of what it's like to fly with Porter Airlines, Delta, and United Airlines from Winnipeg to Illinois 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

Entertainment

7.0

Crew

8.7

Comfort

8.0

Food

7.6

Boarding

8.2

Overall

8.0

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

Entertainment

7.0

Crew

8.7

Comfort

8.0

Food

7.6

Boarding

8.2

Overall

8.0

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
7,980 reviews
Porter Airlines
8.0
Very good
318 reviews

Entertainment

7.0

Crew

8.7

Comfort

8.0

Food

7.6

Boarding

8.2

Overall

8.0

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
8,902 reviews
Porter Airlines
8.0
Very good
318 reviews

Entertainment

7.0

Crew

8.7

Comfort

8.0

Food

7.6

Boarding

8.2

Overall

8.0

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
2,977 reviews
Porter Airlines
8.0
Very good
318 reviews

Entertainment

7.0

Crew

8.7

Comfort

8.0

Food

7.6

Boarding

8.2

Overall

8.0

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
9,842 reviews
Porter Airlines
8.0
Very good
318 reviews

Entertainment

7.0

Crew

8.7

Comfort

8.0

Food

7.6

Boarding

8.2

Overall

8.0

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 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?

    Winnipeg (YWG), located 4.6 mi from the city center, is the airport you fly out of when you book flights from Winnipeg to Illinois.

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

    One-way options have recently been found by users for as low as $160 on WestJet. Other airlines that offer cheap prices include United Airlines from $193 and Air Canada from $198 one-way.

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

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

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

    The top 3 most reliable airlines when flying from Winnipeg to Illinois are Avianca (93%), SkyWest Airlines (91%) and United Airlines (91%).

  • What are the cheapest flights from Winnipeg to Illinois?

    Looking for the cheapest flight from Winnipeg to Illinois? While on average our users pay $509, our data indicates the cheapest price to be $169. The most popular route (Winnipeg - Chicago O'Hare Intl), is priced around $246.

  • 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, August is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of $245). Flying from Winnipeg to Illinois in March is currently the most expensive (average of $321). 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 2 airlines flying from Winnipeg to Illinois

Discover the top 2 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 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$546FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$230Average$645FlexibilityNo cancel feeOn-time67%

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