$190+ Cheap flights from Winnipeg (YWG) to Illinois
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Dec 12 — Dec 191
Round-trip
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
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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 November 12, 2026.
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 November 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Thu 12/109:35 pm -
2 stops24h 54m
Sun 12/1310:29 pm -
1 stop15h 11m
Deal found 11/10![Multiple Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/167:00 am -
1 stop16h 00m
Mon 12/214:59 pm -
2 stops23h 26m
Deal found 11/9![Multiple Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 11/8. 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.
Sun 12/69:35 pm -
2 stops24h 54m
Sun 12/1310:29 pm -
1 stop15h 11m
Deal found 11/8![Multiple Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:35 pm -
2 stops21h 28m
Thu 12/106:20 pm -
1 stop14h 55m
Deal found 11/9![Multiple Airlines logo]()
$439
This Mytrip deal was found by Cheapflights users on 11/9. 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.
Thu 12/39:35 pm -
2 stops21h 28m
Mon 12/710:29 pm -
2 stops17h 56m
Deal found 11/9![Multiple Airlines logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Fri 12/49:35 pm -
2 stops17h 55m
Fri 12/185:58 am -
1 stop7h 42m
Deal found 11/11![Multiple Airlines logo]()
$463
This Mytrip deal was found by Cheapflights users on 11/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/109:35 pm -
2 stops19h 31m
Sun 12/138:37 pm -
3 stops27h 33m
Deal found 11/10![Multiple Airlines logo]()
$475
This WestJet deal was found by Cheapflights users on 11/11. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:25 am -
1 stop11h 25m
Wed 12/95:30 pm -
1 stop17h 01m
Deal found 11/11![WestJet logo]()
$620
This WestJet deal was found by Cheapflights users on 11/7. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:45 pm -
1 stop24h 05m
Sat 12/512:39 pm -
1 stop11h 00m
Deal found 11/7![WestJet logo]()
$623
This FlightHub deal was found by Cheapflights users on 11/8. 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.
Sun 12/69:35 pm -
2 stops13h 53m
Sun 12/136:41 pm -
2 stops25h 09m
Deal found 11/8![WestJet logo]()
$625
This FlightHub deal was found by Cheapflights users on 11/8. 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.
Sun 11/299:05 pm -
2 stops20h 13m
Thu 12/35:30 pm -
1 stop17h 01m
Deal found 11/8![WestJet logo]()
$627
This FlightHub deal was found by Cheapflights users on 11/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:25 am -
1 stop11h 25m
Sun 12/136:41 pm -
2 stops16h 24m
Deal found 11/10![WestJet logo]()
$665
Best flights from Winnipeg to IllinoisDiscover carefully curated flight deals from Winnipeg to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 12, 2026.
Discover carefully curated flight deals from Winnipeg to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 12, 2026.
This Mytrip deal was found by Cheapflights users on 11/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/109:35 pm -
2 stops19h 31m
Sun 12/138:37 pm -
3 stops27h 33m
Deal found 11/10![Multiple Airlines logo]()
$475
This WestJet deal was found by Cheapflights users on 11/11. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:45 pm -
1 stop4h 50m
Sat 12/53:47 pm -
2 stops21h 33m
Deal found 11/11![WestJet logo]()
$539
This Porter Airlines deal was found by Cheapflights users on 11/8. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/37:00 am -
1 stop7h 15m
Sat 1/232:48 pm -
1 stop7h 11m
Deal found 11/8![Porter Airlines logo]()
$654
This United Airlines deal was found by Cheapflights users on 11/11. 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.
Mon 2/88:00 am -
Nonstop2h 45m
Wed 2/1710:51 am -
1 stop10h 06m
Deal found 11/11![United Airlines logo]()
$669
This Delta deal was found by Cheapflights users on 11/8. 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 1/96:00 am -
2 stops17h 17m
Wed 1/209:38 am -
2 stops6h 15m
Deal found 11/8![Delta logo]()
$721
This WestJet deal was found by Cheapflights users on 11/11. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:25 am -
1 stop11h 25m
Wed 12/95:30 pm -
1 stop17h 01m
Deal found 11/11![WestJet logo]()
$620
This United Airlines deal was found by Cheapflights users on 11/8. 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 1/78:00 am -
Nonstop2h 45m
Wed 1/203:50 pm -
Nonstop2h 38m
Deal found 11/8![United Airlines logo]()
$673
This WestJet deal was found by Cheapflights users on 11/8. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/75:45 pm -
1 stop24h 08m
Wed 1/209:56 am -
1 stop13h 43m
Deal found 11/8![WestJet logo]()
$649
This United Airlines deal was found by Cheapflights users on 11/10. 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.
Fri 3/197:00 am -
Nonstop2h 31m
Mon 3/223:50 pm -
Nonstop2h 51m
Deal found 11/10![United Airlines logo]()
$675
This Delta deal was found by Cheapflights users on 11/9. 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.
Fri 12/257:00 am -
2 stops11h 44m
Wed 12/309:29 am -
2 stops10h 21m
Deal found 11/9![Delta logo]()
$761
This Justfly.com deal was found by Cheapflights users on 11/11. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/87:00 am -
1 stop10h 54m
Wed 2/179:46 am -
1 stop25h 09m
Deal found 11/11![WestJet logo]()
$660
This United Airlines deal was found by Cheapflights users on 11/7. 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 12/103:15 pm -
Nonstop2h 45m
Sun 12/139:35 am -
Nonstop2h 48m
Deal found 11/7![United Airlines logo]()
$677
This United Airlines deal was found by Cheapflights users on 11/8. 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 2/259:40 am -
1 stop14h 06m
Sun 2/2810:51 am -
1 stop10h 06m
Deal found 11/8![United Airlines logo]()
$678
This United Airlines deal was found by Cheapflights users on 11/8. 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 1/99:40 am -
1 stop11h 21m
Wed 1/203:50 pm -
Nonstop2h 38m
Deal found 11/8![United Airlines logo]()
$678
This FlightHub deal was found by Cheapflights users on 11/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/299:35 pm -
2 stops13h 49m
Thu 12/312:39 pm -
2 stops31h 11m
Deal found 11/12![WestJet logo]()
$757
This Delta deal was found by Cheapflights users on 11/11. 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 12/1912:22 pm -
1 stop6h 02m
Fri 12/256:00 am -
1 stop7h 40m
Deal found 11/11![Delta logo]()
$945
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Wed 1/69:40 am -
1 stop8h 25m
Wed 1/203:50 pm -
Nonstop2h 38m
Deal found 11/8![United Airlines logo]()
$678
This United Airlines deal was found by Cheapflights users on 11/9. 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.
Mon 2/88:00 am -
1 stop6h 44m
Tue 2/1610:39 am -
1 stop7h 47m
Deal found 11/9![United Airlines logo]()
$679
This FlightHub deal was found by Cheapflights users on 11/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/259:05 pm -
2 stops12h 55m
Sun 2/289:33 am -
2 stops15h 11m
Deal found 11/9![WestJet logo]()
$831
Last-minute flights from Winnipeg to IllinoisDiscover last-minute flight deals from Winnipeg to Illinois. Data last updated November 12, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Illinois. Data last updated November 12, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 11/8. 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.
Sun 11/299:05 pm -
2 stops20h 13m
Thu 12/35:30 pm -
1 stop17h 01m
Deal found 11/8![WestJet logo]()
$627
This WestJet deal was found by Cheapflights users on 11/7. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:45 pm -
1 stop24h 05m
Sat 12/512:39 pm -
1 stop11h 00m
Deal found 11/7![WestJet logo]()
$623
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:35 pm -
2 stops21h 28m
Thu 12/106:20 pm -
1 stop14h 55m
Deal found 11/9![Multiple Airlines logo]()
$439
This Mytrip deal was found by Cheapflights users on 11/9. 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.
Thu 12/39:35 pm -
2 stops21h 28m
Mon 12/710:29 pm -
2 stops17h 56m
Deal found 11/9![Multiple Airlines logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Fri 12/49:35 pm -
2 stops17h 55m
Fri 12/185:58 am -
1 stop7h 42m
Deal found 11/11![Multiple Airlines logo]()
$463
This Kiwi.com deal was found by Cheapflights users on 11/8. 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.
Sun 12/69:35 pm -
2 stops24h 54m
Sun 12/1310:29 pm -
1 stop15h 11m
Deal found 11/8![Multiple Airlines logo]()
$437
This FlightHub deal was found by Cheapflights users on 11/8. 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.
Sun 12/69:35 pm -
2 stops13h 53m
Sun 12/136:41 pm -
2 stops25h 09m
Deal found 11/8![WestJet logo]()
$625
This WestJet deal was found by Cheapflights users on 11/11. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:25 am -
1 stop11h 25m
Wed 12/95:30 pm -
1 stop17h 01m
Deal found 11/11![WestJet logo]()
$620
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Thu 12/109:35 pm -
2 stops24h 54m
Sun 12/1310:29 pm -
1 stop15h 11m
Deal found 11/10![Multiple Airlines logo]()
$390
This Mytrip deal was found by Cheapflights users on 11/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/109:35 pm -
2 stops19h 31m
Sun 12/138:37 pm -
3 stops27h 33m
Deal found 11/10![Multiple Airlines logo]()
$475
This FlightHub deal was found by Cheapflights users on 11/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:25 am -
1 stop11h 25m
Sun 12/136:41 pm -
2 stops16h 24m
Deal found 11/10![WestJet logo]()
$665
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/167:00 am -
1 stop16h 00m
Mon 12/214:59 pm -
2 stops23h 26m
Deal found 11/9![Multiple Airlines logo]()
$404
One-way flights from Winnipeg to IllinoisSearch for one-way flight options from Winnipeg to Illinois. Find affordable one-way fares based on user searches. Data last updated November 12, 2026.
Search for one-way flight options from Winnipeg to Illinois. Find affordable one-way fares based on user searches. Data last updated November 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/159:35 pm -
2 stops25h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 12/149:35 pm -
2 stops25h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$192
This Trip.com deal was found by Cheapflights users on 11/8. 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.
Wed 12/167:00 am -
1 stop16h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Multiple Airlines logo]()
$197
This Trip.com deal was found by Cheapflights users on 11/10. 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.
Wed 12/167:00 am -
1 stop15h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Wed 12/99:35 pm -
2 stops34h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$206
This Trip.com deal was found by Cheapflights users on 11/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:35 pm -
2 stops17h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Multiple Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 11/309:35 pm -
2 stops25h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/19:35 pm -
2 stops17h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Thu 12/39:35 pm -
2 stops21h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Multiple Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Wed 12/29:35 pm -
2 stops24h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/19:35 pm -
2 stops14h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$233
This FlightHub deal was found by Cheapflights users on 11/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/159:35 pm -
2 stops19h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![WestJet logo]()
$241
Find flight deals from Winnipeg to Illinois
Keep the following information in mind while searching for Winnipeg to Illinois flight deals. Data was last updated November 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $376 (Kiwi.com) |
One-way from | $190 (Trip.com) |
Popular in | June |
Cheapest in | February |
Average price | $561 |
Good round-trip deal | $475 or less |
Good one-way deal | $402 or less |
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 7,457,451 searches. Data last updated November 12, 2026.
Use the filters below to find and compare flights from Winnipeg to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Wed 12/16
7:00 am-10:00 pm
1 stop16h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$203
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Tue 12/1
9:35 pm-2:00 pm
2 stops17h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$222
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Tue 12/15
9:35 pm-4:16 pm
2 stops19h 41m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$241
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Wed 12/9
9:35 pm-10:28 am
2 stops13h 53m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$247
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Wed 12/16
9:35 pm-11:17 pm
2 stops26h 42m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$248
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Tue 12/1
7:00 am-1:10 pm
1 stop7h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$299
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Wed 12/23
7:00 am-1:15 pm
1 stop7h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$310
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Wed 12/23
7:00 am-12:01 am
1 stop18h 01m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$310
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Tue 12/22
7:00 am-1:15 pm
1 stop7h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$311
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Tue 12/1
5:45 pm-4:50 pm
1 stop24h 05m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$330
Showing 1-10 of 38 resultsSorted by cheapest first
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.
YWG-ORD
YWG-MDW
YWG-MLI
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
YWG-USIL
YWG-ORD
YWG-MDW
YWG-MLI
What is the cheapest month to book a flight from Winnipeg to Illinois?
Currently, February is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of $523). Flying from Winnipeg to Illinois in October is currently the most expensive (average of $755). 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 November 12, 2026.
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 November 12, 2026.
The most flights from YWG to USIL are scheduled on a Monday (4 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Winnipeg to Illinois?
Airfare is below average for this route at the moment.
Winnipeg to Illinois flights typically cost between $504 and $701 in February.The cheapest round-trip price found within the last 5 days was $376 on Multiple Airlines (Feb 8-Feb 17).
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 November 12, 2026.
Get a feel of what it's like to fly with United Airlines and Air Canada 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.
Overall
7.3
Crew
8.1
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Overall
7.3
Crew
8.1
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Overall
7.3
Crew
8.1
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
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
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Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Winnipeg to Illinois by cabin class
Find flights from Winnipeg to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Winnipeg and Illinois flights
Browse other Winnipeg and Illinois flight options. Last updated on November 12, 2026.
Popular flight searches
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Winnipeg to Illinois flights
Consider these flights traveling from Winnipeg to Illinois.
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 7,457,451 searches. Data last updated November 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$517 | Average$702 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$629 | Average$1,130 | FlexibilityNo cancel fee | On-time67% |