$166+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Sep 9 — Sep 161
Round-trip
1 adult, Economy
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Find cheap flights from Winnipeg to Illinois with Cheapflights
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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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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 August 10, 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 August 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 9/1011:15 am -
2 stops23h 45m
Sun 9/1311:45 am -
1 stop22h 00m
Deal found 8/10![Multiple Airlines logo]()
$320
This Justfly.com deal was found by Cheapflights users on 8/9. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:00 am -
1 stop9h 40m
Sun 9/135:30 pm -
1 stop7h 25m
Deal found 8/9![WestJet logo]()
$351
This Mytrip deal was found by Cheapflights users on 8/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:55 pm -
1 stop23h 45m
Sat 9/55:30 pm -
1 stop7h 25m
Deal found 8/7![WestJet logo]()
$357
This Mytrip deal was found by Cheapflights users on 8/6. 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 8/287:10 pm -
1 stop21h 30m
Mon 8/315:30 pm -
1 stop7h 25m
Deal found 8/6![WestJet logo]()
$364
This Mytrip deal was found by Cheapflights users on 8/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:05 pm -
1 stop14h 55m
Tue 9/299:55 am -
1 stop9h 54m
Deal found 8/8![Multiple Airlines logo]()
$370
This Mytrip deal was found by Cheapflights users on 8/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:00 am -
1 stop9h 40m
Thu 9/35:30 pm -
1 stop21h 55m
Deal found 8/7![WestJet logo]()
$373
This FlightHub deal was found by Cheapflights users on 8/8. 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.
Thu 10/19:05 pm -
1 stop19h 35m
Thu 10/225:30 pm -
1 stop7h 25m
Deal found 8/8![WestJet logo]()
$380
This Justfly.com deal was found by Cheapflights users on 8/8. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/412:46 pm -
1 stop10h 40m
Tue 9/85:47 pm -
1 stop21h 21m
Deal found 8/8![WestJet logo]()
$467
This Mytrip deal was found by Cheapflights users on 8/10. 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 9/108:45 pm -
1 stop14h 15m
Sun 9/1311:45 am -
1 stop8h 04m
Deal found 8/10![Porter Airlines logo]()
$481
This Delta deal was found by Cheapflights users on 8/6. 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 10/135:40 pm -
1 stop5h 41m
Sat 10/175:33 pm -
1 stop5h 46m
Deal found 8/6![Delta logo]()
$483
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 8/2712:15 pm -
1 stop21h 30m
Mon 8/313:15 pm -
1 stop18h 30m
Deal found 8/6![Multiple Airlines logo]()
$539
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Fri 9/1111:15 am -
2 stops23h 45m
Mon 9/147:13 pm -
1 stop16h 38m
Deal found 8/8![Multiple Airlines logo]()
$545
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 August 10, 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 August 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 9/107:00 am -
1 stop9h 40m
Sun 9/135:30 pm -
1 stop7h 25m
Deal found 8/9![WestJet logo]()
$365
This Mytrip deal was found by Cheapflights users on 8/10. 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 9/1011:15 am -
2 stops8h 33m
Sun 9/138:45 am -
2 stops25h 00m
Deal found 8/10![Multiple Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 8/6. 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 10/135:40 pm -
1 stop5h 41m
Sat 10/175:33 pm -
1 stop5h 46m
Deal found 8/6![Delta logo]()
$483
This Porter Airlines deal was found by Cheapflights users on 8/6. 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.
Wed 9/1611:40 am -
2 stops8h 40m
Sat 9/198:03 am -
1 stop7h 16m
Deal found 8/6![Porter Airlines logo]()
$518
This Air Canada deal was found by Cheapflights users on 8/10. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:20 pm -
1 stop7h 28m
Sun 9/137:54 pm -
Nonstop2h 39m
Deal found 8/10![Air Canada logo]()
$559
This United Airlines deal was found by Cheapflights users on 8/5. 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 10/58:45 am -
1 stop11h 51m
Wed 10/71:36 pm -
1 stop7h 21m
Deal found 8/5![United Airlines logo]()
$573
This FlightHub deal was found by Cheapflights users on 8/10. 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.
Fri 9/257:00 am -
2 stops9h 40m
Sun 9/275:30 pm -
1 stop7h 25m
Deal found 8/10![WestJet logo]()
$432
This Justfly.com deal was found by Cheapflights users on 8/8. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/412:46 pm -
1 stop10h 40m
Tue 9/85:47 pm -
1 stop21h 21m
Deal found 8/8![WestJet logo]()
$467
This Porter Airlines deal was found by Cheapflights users on 8/7. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/79:20 am -
1 stop6h 59m
Thu 10/158:06 am -
1 stop7h 13m
Deal found 8/7![Porter Airlines logo]()
$533
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 8/2812:15 pm -
1 stop21h 25m
Mon 8/313:15 pm -
1 stop18h 30m
Deal found 8/6![Multiple Airlines logo]()
$555
This Delta deal was found by Cheapflights users on 8/5. 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 10/55:44 pm -
2 stops15h 25m
Wed 10/73:35 pm -
1 stop4h 18m
Deal found 8/5![Delta logo]()
$578
This Porter Airlines deal was found by Cheapflights users on 8/9. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
1 stop7h 37m
Sun 11/222:50 pm -
1 stop7h 07m
Deal found 8/9![Porter Airlines logo]()
$546
This Delta deal was found by Cheapflights users on 8/8. 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.
Tue 9/2212:41 pm -
1 stop5h 38m
Tue 9/299:59 am -
1 stop5h 09m
Deal found 8/8![Delta logo]()
$579
This Porter Airlines deal was found by Cheapflights users on 8/8. 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.
Sat 9/199:20 am -
1 stop6h 58m
Wed 10/218:06 am -
2 stops9h 52m
Deal found 8/8![Porter Airlines logo]()
$553
This Delta deal was found by Cheapflights users on 8/8. 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.
Fri 9/255:44 pm -
1 stop3h 49m
Sat 10/245:30 pm -
1 stop5h 49m
Deal found 8/8![Delta logo]()
$579
This oojo deal was found by Cheapflights users on 8/7. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/139:05 pm -
2 stops12h 58m
Sun 10/181:27 pm -
2 stops11h 28m
Deal found 8/7![WestJet logo]()
$591
This Porter Airlines deal was found by Cheapflights users on 8/9. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:20 am -
1 stop6h 58m
Wed 9/308:30 pm -
2 stops14h 13m
Deal found 8/9![Porter Airlines logo]()
$557
This oojo deal was found by Cheapflights users on 8/7. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:00 am -
2 stops11h 01m
Thu 9/39:59 am -
2 stops11h 41m
Deal found 8/7![WestJet logo]()
$591
This oojo deal was found by Cheapflights users on 8/10. 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.
Sun 9/66:15 am -
2 stops10h 44m
Mon 9/149:24 am -
2 stops15h 31m
Deal found 8/10![WestJet logo]()
$600
This Delta deal was found by Cheapflights users on 8/8. 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.
Thu 8/2712:46 pm -
1 stop5h 15m
Wed 9/27:25 pm -
1 stop16h 29m
Deal found 8/8![Delta logo]()
$726
This oojo deal was found by Cheapflights users on 8/5. 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 11/135:00 am -
2 stops13h 04m
Tue 11/1711:28 am -
2 stops12h 27m
Deal found 8/5![WestJet logo]()
$616
This WestJet deal was found by Cheapflights users on 8/6. 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 10/135:40 pm -
1 stop5h 41m
Sat 10/176:47 am -
2 stops7h 38m
Deal found 8/6![WestJet logo]()
$629
This FlightHub deal was found by Cheapflights users on 8/5. 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 9/104:25 pm -
2 stops23h 52m
Sat 9/129:29 am -
2 stops10h 51m
Deal found 8/5![WestJet logo]()
$671
This WestJet deal was found by Cheapflights users on 8/5. 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.
Sun 9/2710:30 pm -
2 stops19h 49m
Tue 9/297:13 pm -
1 stop16h 38m
Deal found 8/5![WestJet logo]()
$696
Last-minute flights from Winnipeg to IllinoisDiscover last-minute flight deals from Winnipeg to Illinois. Data last updated August 10, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Illinois. Data last updated August 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 8/2712:15 pm -
1 stop21h 30m
Mon 8/313:15 pm -
1 stop18h 30m
Deal found 8/6![Multiple Airlines logo]()
$539
This Mytrip deal was found by Cheapflights users on 8/6. 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 8/287:10 pm -
1 stop21h 30m
Mon 8/315:30 pm -
1 stop7h 25m
Deal found 8/6![WestJet logo]()
$364
This Mytrip deal was found by Cheapflights users on 8/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:55 pm -
1 stop23h 45m
Sat 9/55:30 pm -
1 stop7h 25m
Deal found 8/7![WestJet logo]()
$357
This Mytrip deal was found by Cheapflights users on 8/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:00 am -
1 stop9h 40m
Thu 9/35:30 pm -
1 stop21h 55m
Deal found 8/7![WestJet logo]()
$373
This Justfly.com deal was found by Cheapflights users on 8/8. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/412:46 pm -
1 stop10h 40m
Tue 9/85:47 pm -
1 stop21h 21m
Deal found 8/8![WestJet logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 9/1011:15 am -
2 stops23h 45m
Sun 9/1311:45 am -
1 stop22h 00m
Deal found 8/10![Multiple Airlines logo]()
$320
This Justfly.com deal was found by Cheapflights users on 8/9. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:00 am -
1 stop9h 40m
Sun 9/135:30 pm -
1 stop7h 25m
Deal found 8/9![WestJet logo]()
$351
This Mytrip deal was found by Cheapflights users on 8/10. 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 9/108:45 pm -
1 stop14h 15m
Sun 9/1311:45 am -
1 stop8h 04m
Deal found 8/10![Porter Airlines logo]()
$481
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Fri 9/1111:15 am -
2 stops23h 45m
Mon 9/147:13 pm -
1 stop16h 38m
Deal found 8/8![Multiple Airlines logo]()
$545
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Sat 9/1211:15 am -
2 stops23h 45m
Tue 9/159:59 am -
1 stop6h 55m
Deal found 8/9![Multiple Airlines logo]()
$548
This Delta deal was found by Cheapflights users on 8/6. 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 9/165:44 pm -
2 stops15h 23m
Sat 9/194:30 pm -
2 stops19h 21m
Deal found 8/6![Delta logo]()
$547
This Mytrip deal was found by Cheapflights users on 8/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:05 pm -
1 stop14h 55m
Tue 9/299:55 am -
1 stop9h 54m
Deal found 8/8![Multiple Airlines logo]()
$370
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 August 10, 2026.
Search for one-way flight options from Winnipeg to Illinois. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:15 am -
2 stops33h 05m
Deal found 8/7![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 9/911:15 am -
2 stops23h 45m
Deal found 8/10![Porter Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 9/2111:15 am -
2 stops23h 45m
Deal found 8/10![Porter Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1711:15 am -
2 stops23h 45m
Deal found 8/7![Porter Airlines logo]()
$176
This Mytrip deal was found by Cheapflights users on 8/6. 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.
Sat 9/57:00 am -
1 stop9h 40m
Deal found 8/6![WestJet logo]()
$189
This Booking.com deal was found by Cheapflights users on 8/6. 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.
Tue 9/17:00 am -
1 stop9h 40m
Deal found 8/6![WestJet logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 9/37:00 am -
1 stop9h 40m
Deal found 8/9![WestJet logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Sat 9/511:15 am -
2 stops27h 20m
Deal found 8/5![Porter Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Sat 8/297:00 am -
1 stop9h 40m
Deal found 8/8![WestJet logo]()
$213
This Trip.com deal was found by Cheapflights users on 8/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:10 pm -
1 stop21h 30m
Deal found 8/7![WestJet logo]()
$220
This Flightnetwork deal was found by Cheapflights users on 8/7. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:00 am -
1 stop9h 40m
Deal found 8/7![WestJet logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Sat 9/55:10 pm -
2 stops25h 29m
Deal found 8/6![Multiple Airlines logo]()
$229
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 August 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $351 (Justfly.com) |
One-way from | $166 (Kiwi.com) |
Popular in | January |
Cheapest in | October |
Average price | $668 |
Good round-trip deal | $551 or less |
Good one-way deal | $384 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 2,558,603 searches. Data last updated August 10, 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
Thu 9/10
7:00 am-4:40 pm
1 stop9h 40m
Chicago O'Hare Intl
Sun 9/13
5:30 pm-12:55 am
1 stop7h 25m
$365
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Thu 9/10
11:15 am-7:48 pm
2 stops8h 33m
Chicago O'Hare Intl
Sun 9/13
8:45 am-9:45 am
2 stops25h 00m
$414
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Fri 9/25
7:00 am-4:40 pm
2 stops9h 40m
Chicago O'Hare Intl
Sun 9/27
5:30 pm-12:55 am
1 stop7h 25m
$432
WinnipegSt. Louis
YWG Winnipeg - STL Lambert-St Louis
YWGSTL
Winnipeg
Fri 9/4
12:46 pm-11:26 pm
1 stop10h 40m
Lambert-St Louis
Tue 9/8
5:47 pm-3:08 pm
1 stop21h 21m
$467
WinnipegSt. Louis
YWG Winnipeg - STL Lambert-St Louis
YWGSTL
Winnipeg
Tue 10/13
5:40 pm-11:21 pm
1 stop5h 41m
Lambert-St Louis
Sat 10/17
5:33 pm-11:19 pm
1 stop5h 46m
$483
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Wed 9/16
11:40 am-8:20 pm
2 stops8h 40m
Chicago O'Hare Intl
Sat 9/19
8:03 am-3:19 pm
1 stop7h 16m
$518
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Wed 10/7
9:20 am-4:19 pm
1 stop6h 59m
Chicago O'Hare Intl
Thu 10/15
8:06 am-3:19 pm
1 stop7h 13m
$533
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Wed 11/18
7:00 am-2:37 pm
1 stop7h 37m
Chicago O'Hare Intl
Sun 11/22
2:50 pm-9:57 pm
1 stop7h 07m
$546
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Sat 9/19
9:20 am-4:18 pm
1 stop6h 58m
Chicago O'Hare Intl
Wed 10/21
8:06 am-5:58 pm
2 stops9h 52m
$553
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Fri 8/28
12:15 pm-9:40 am
1 stop21h 25m
Chicago Midway
Mon 8/31
3:15 pm-9:45 am
1 stop18h 30m
$555
Showing 1-10 of 44 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-STL
YWG-MDW
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-STL
YWG-MDW
What is the cheapest month to book a flight from Winnipeg to Illinois?
Currently, September is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of $380). Flying from Winnipeg to Illinois in June is currently the most expensive (average of $692). 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 August 10, 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.
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 $509 and $692 in September.The cheapest round-trip price found within the last 5 days was $351 on WestJet (Sep 10-Sep 13).
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 August 10, 2026.
Get a feel of what it's like to fly with 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.
Boarding
7.7
Overall
7.4
Entertainment
7.1
Crew
8.1
Comfort
7.3
Food
6.7
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Boarding
7.7
Overall
7.4
Entertainment
7.1
Crew
8.1
Comfort
7.3
Food
6.7
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - 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
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Winnipeg and Illinois flights
Browse other Winnipeg and Illinois flight options. Last updated on August 10, 2026.
Popular flight searches
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Winnipeg to Illinois flights
Consider these flights traveling from Winnipeg to Illinois.
Top airline flying from Winnipeg to Illinois
Discover the top airline 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 August 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$335 | Average$657 | FlexibilityNo cancel fee | On-time69% |