$152+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Jun 17 — Jun 241
1 adult, Economy
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Find cheap flights from Winnipeg to Illinois with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 June 12, 2025.
Round-trip from | $240 (Trip.com) |
|---|---|
One-way from | $152 (Kiwi.com) |
Popular in | April |
Cheapest in | June |
Average price | $408 |
Good round-trip deal | $340 or less |
Good one-way deal | $227 or less |
Find flight deals from Winnipeg to Illinois
Cheapest flights from Winnipeg to IllinoisExplore 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 June 12, 2025.
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 June 12, 2025.
This Trip.com deal was found by Cheapflights users on 6/10. 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 10/38:30 amYWG - ORD
1 stop8h 13mWestJet
Sun 10/51:40 pmORD - YWG
1 stop7h 45mWestJet
Deal found 6/10![WestJet logo]()
$240
This Mytrip deal was found by Cheapflights users on 6/9. 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.
Mon 6/239:00 amYWG - ORD
1 stop24h 38mMultiple Airlines
Mon 6/3010:43 amORD - YWG
2 stops32h 41mMultiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 6/11. 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 9/1912:40 pmYWG - MDW
1 stop5h 27mDelta
Tue 9/231:00 pmMDW - YWG
2 stops10h 32mDelta
Deal found 6/11![Delta logo]()
$453
This United Airlines deal was found by Cheapflights users on 6/10. 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 8/282:20 pmYWG - ORD
Nonstop2h 31mUnited Airlines
Tue 9/27:15 amORD - YWG
1 stop5h 54mUnited Airlines
Deal found 6/10![United Airlines logo]()
$453
This Air Canada deal was found by Cheapflights users on 6/12. 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.
Wed 8/65:00 amYWG - ORD
1 stop8h 13mAir Canada
Sun 8/109:55 amORD - YWG
1 stop6h 23mAir Canada
Deal found 6/12![Air Canada logo]()
$467
This Delta deal was found by Cheapflights users on 6/10. 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 8/28:35 amYWG - ORD
1 stop8h 15mDelta
Sat 8/96:00 amORD - YWG
1 stop5h 31mDelta
Deal found 6/10![Delta logo]()
$482
This oojo deal was found by Cheapflights users on 6/10. 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.
Fri 7/259:00 amYWG - MDW
1 stop12h 42mWestJet
Mon 7/286:20 pmMDW - YWG
2 stops19h 23mWestJet
Deal found 6/10![WestJet logo]()
$489
This Mytrip deal was found by Cheapflights users on 6/9. 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.
Mon 6/2311:45 amYWG - MDW
2 stops21h 00mPorter Airlines
Mon 6/305:50 pmMDW - YWG
2 stops28h 56mPorter Airlines
Deal found 6/9![Porter Airlines logo]()
$497
This Delta deal was found by Cheapflights users on 6/9. 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 7/85:42 pmYWG - STL
2 stops14h 40mDelta
Tue 7/157:00 amSTL - YWG
2 stops16h 25mDelta
Deal found 6/9![Delta logo]()
$498
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Tue 7/153:15 pmYWG - STL
3 stops19h 14mMultiple Airlines
Fri 8/19:50 amSTL - YWG
3 stops14h 23mMultiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$515
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Tue 7/87:00 amYWG - STL
1 stop7h 37mUnited Airlines
Tue 7/155:15 amSTL - YWG
1 stop7h 54mUnited Airlines
Deal found 6/9![United Airlines logo]()
$543
This Air Canada deal was found by Cheapflights users on 6/9. 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 8/85:00 amYWG - STL
1 stop14h 45mAir Canada
Sun 8/109:15 amSTL - YWG
1 stop7h 03mAir Canada
Deal found 6/9![Air Canada logo]()
$587
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 June 12, 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 10/3
8:30 am-4:43 pm
1 stop8h 13m
Chicago O'Hare Intl
Sun 10/5
1:40 pm-9:25 pm
1 stop7h 45m
$240
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Mon 6/23
9:00 am-9:38 am
1 stop24h 38m
Chicago O'Hare Intl
Mon 6/30
10:43 am-7:24 pm
2 stops32h 41m
$304
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Fri 9/19
12:40 pm-6:07 pm
1 stop5h 27m
Chicago Midway
Tue 9/23
1:00 pm-11:32 pm
2 stops10h 32m
$453
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Thu 8/28
2:20 pm-4:51 pm
Nonstop2h 31m
Chicago O'Hare Intl
Tue 9/2
7:15 am-1:09 pm
1 stop5h 54m
$453
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Wed 8/6
5:00 am-1:13 pm
1 stop8h 13m
Chicago O'Hare Intl
Sun 8/10
9:55 am-4:18 pm
1 stop6h 23m
$467
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Sat 8/2
8:35 am-4:50 pm
1 stop8h 15m
Chicago O'Hare Intl
Sat 8/9
6:00 am-11:31 am
1 stop5h 31m
$482
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Fri 7/25
9:00 am-9:42 pm
1 stop12h 42m
Chicago Midway
Mon 7/28
6:20 pm-1:43 pm
2 stops19h 23m
$489
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Mon 6/23
11:45 am-8:45 am
2 stops21h 00m
Chicago Midway
Mon 6/30
5:50 pm-10:46 pm
2 stops28h 56m
$497
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Tue 7/8
5:42 pm-8:22 am
2 stops14h 40m
Lambert-St Louis
Tue 7/15
7:00 am-11:25 pm
2 stops16h 25m
$498
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Tue 7/15
3:15 pm-10:29 am
3 stops19h 14m
Lambert-St Louis
Fri 8/1
9:50 am-12:13 am
3 stops14h 23m
$515
Showing 1-10 of 24 results
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 June 12, 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 June 12, 2025.
The most flights from YWG to USIL are scheduled on a Monday (8 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 on average).
Rainfall in Illinois by month
Plan your trip to Illinois by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.
Temperature in Illinois by month
Plan your trip to Illinois by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
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 June 12, 2025.
Read reviews from past customers who have flown Porter Airlines, Delta and United Airlines from Winnipeg to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.7
Overall
8.0
Food
7.6
Comfort
8.1
Entertainment
7.0
Boarding
8.2
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Crew
8.7
Overall
8.0
Food
7.6
Comfort
8.1
Entertainment
7.0
Boarding
8.2
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Crew
8.7
Overall
8.0
Food
7.6
Comfort
8.1
Entertainment
7.0
Boarding
8.2
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Crew
8.7
Overall
8.0
Food
7.6
Comfort
8.1
Entertainment
7.0
Boarding
8.2
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Crew
8.7
Overall
8.0
Food
7.6
Comfort
8.1
Entertainment
7.0
Boarding
8.2
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Crew
8.7
Overall
8.0
Food
7.6
Comfort
8.1
Entertainment
7.0
Boarding
8.2
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
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.
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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.
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 June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$230 | Average$572 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$443 | Average$562 | FlexibilityNo cancel fee | On-time69% |