$111+ 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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Jun 17 — Jun 241
1 adult, Economy
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Find cheap flights from Illinois to Winnipeg 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 Illinois to Winnipeg
Keep the following information in mind while searching for Illinois to Winnipeg flight deals. Data was last updated June 12, 2025.
Round-trip from | $258 (Kiwi.com) |
|---|---|
One-way from | $111 (Kiwi.com) |
Popular in | February |
Cheapest in | May |
Average price | $566 |
Good round-trip deal | $552 or less |
Good one-way deal | $284 or less |
Find flight deals from Illinois to Winnipeg
Cheapest flights from Illinois to WinnipegExplore 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 June 12, 2025.
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 June 12, 2025.
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/810:43 amORD - YWG
2 stops13h 48mMultiple Airlines
Fri 7/119:00 amYWG - ORD
1 stop12h 30mMultiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$258
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:30 pmORD - YWG
1 stop28h 00mWestJet
Mon 10/208:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 6/12![WestJet logo]()
$287
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/226:15 amMDW - YWG
1 stop10h 07mMultiple Airlines
Thu 9/259:00 amYWG - MDW
1 stop9h 18mMultiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$314
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.
Mon 9/229:30 amMDW - YWG
2 stops14h 02mDelta
Tue 9/306:40 amYWG - MDW
2 stops15h 04mDelta
Deal found 6/11![Delta logo]()
$404
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.
Sat 9/2710:35 amORD - YWG
2 stops12h 57mDelta
Tue 9/306:40 amYWG - ORD
2 stops17h 13mDelta
Deal found 6/11![Delta logo]()
$431
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.
Thu 7/39:50 amSTL - YWG
2 stops30h 05mMultiple Airlines
Mon 7/78:55 pmYWG - STL
3 stops37h 34mMultiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$497
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/289:50 amORD - YWG
1 stop6h 08mAir Canada
Fri 11/75:15 amYWG - ORD
1 stop5h 43mAir Canada
Deal found 6/11![Air Canada logo]()
$513
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.
Fri 7/189:40 amMDW - YWG
2 stops13h 06mPorter Airlines
Sun 7/206:55 pmYWG - MDW
1 stop13h 50mPorter Airlines
Deal found 6/11![Porter Airlines logo]()
$543
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/289:20 amMDW - YWG
2 stops10h 15mWestJet
Fri 11/75:00 amYWG - MDW
2 stops16h 44mWestJet
Deal found 6/12![WestJet logo]()
$596
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/71:30 pmSTL - YWG
1 stop6h 59mAir Canada
Sun 8/107:40 amYWG - STL
1 stop7h 41mAir Canada
Deal found 6/11![Air Canada logo]()
$689
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/38:00 amSTL - YWG
1 stop7h 31mUnited Airlines
Mon 7/77:00 amYWG - STL
1 stop5h 27mUnited Airlines
Deal found 6/11![United Airlines logo]()
$697
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.
Thu 7/3111:18 amSTL - YWG
1 stop8h 52mDelta
Sat 8/96:45 amYWG - STL
2 stops7h 51mDelta
Deal found 6/11![Delta logo]()
$706
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 June 12, 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
Tue 7/8
10:43 am-12:31 am
2 stops13h 48m
Winnipeg
Fri 7/11
9:00 am-9:30 pm
1 stop12h 30m
$258
ChicagoWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Fri 10/17
5:30 pm-9:30 pm
1 stop28h 00m
Winnipeg
Mon 10/20
8:30 am-4:43 pm
1 stop8h 13m
$287
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Mon 9/22
6:15 am-4:22 pm
1 stop10h 07m
Winnipeg
Thu 9/25
9:00 am-6:18 pm
1 stop9h 18m
$314
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Mon 9/22
9:30 am-11:32 pm
2 stops14h 02m
Winnipeg
Tue 9/30
6:40 am-9:44 pm
2 stops15h 04m
$404
ChicagoWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Sat 9/27
10:35 am-11:32 pm
2 stops12h 57m
Winnipeg
Tue 9/30
6:40 am-11:53 pm
2 stops17h 13m
$431
St. LouisWinnipeg
STL - YWG
STLYWG
Lambert-St Louis
Thu 7/3
9:50 am-3:55 pm
2 stops30h 05m
Winnipeg
Mon 7/7
8:55 pm-10:29 am
3 stops37h 34m
$497
ChicagoWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Tue 10/28
9:50 am-3:58 pm
1 stop6h 08m
Winnipeg
Fri 11/7
5:15 am-10:58 am
1 stop5h 43m
$513
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Fri 7/18
9:40 am-10:46 pm
2 stops13h 06m
Winnipeg
Sun 7/20
6:55 pm-8:45 am
1 stop13h 50m
$543
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Tue 10/28
9:20 am-7:35 pm
2 stops10h 15m
Winnipeg
Fri 11/7
5:00 am-9:44 pm
2 stops16h 44m
$596
St. LouisWinnipeg
STL - YWG
STLYWG
Lambert-St Louis
Thu 8/7
1:30 pm-8:29 pm
1 stop6h 59m
Winnipeg
Sun 8/10
7:40 am-3:21 pm
1 stop7h 41m
$689
Showing 1-10 of 21 results
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 June 12, 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 June 12, 2025.
The most flights from USIL to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).
Rainfall in Winnipeg by month
Plan your trip to Winnipeg by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.
Temperature in Winnipeg by month
Plan your trip to Winnipeg by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Winnipeg, 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 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).
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 June 12, 2025.
Read reviews from past customers who have flown Porter Airlines, Delta and United Airlines from Illinois to Winnipeg. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.0
Crew
8.7
Overall
8.0
Comfort
8.1
Boarding
8.2
Food
7.6
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Entertainment
7.0
Crew
8.7
Overall
8.0
Comfort
8.1
Boarding
8.2
Food
7.6
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Entertainment
7.0
Crew
8.7
Overall
8.0
Comfort
8.1
Boarding
8.2
Food
7.6
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Entertainment
7.0
Crew
8.7
Overall
8.0
Comfort
8.1
Boarding
8.2
Food
7.6
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Entertainment
7.0
Crew
8.7
Overall
8.0
Comfort
8.1
Boarding
8.2
Food
7.6
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Entertainment
7.0
Crew
8.7
Overall
8.0
Comfort
8.1
Boarding
8.2
Food
7.6
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
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.
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Alternative routes for Illinois to Winnipeg
See prices for flight routes from nearby airports that may be better suited for you.
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 June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$230 | Average$601 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$354 | Average$641 | FlexibilityNo cancel fee | On-time69% |