$191+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Oct 28 — Nov 41
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 September 28, 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 September 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/227:00 am -
1 stop9h 40m
Tue 10/277:15 am -
2 stops34h 10m
Deal found 9/27![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 10/237:00 am -
1 stop9h 40m
Mon 10/267:44 pm -
2 stops21h 41m
Deal found 9/25![Multiple Airlines logo]()
$379
This Mytrip deal was found by Cheapflights users on 9/24. 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 11/188:35 pm -
2 stops22h 10m
Sat 11/215:26 pm -
2 stops22h 59m
Deal found 9/24![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 12/147:00 am -
1 stop7h 55m
Thu 12/249:23 pm -
1 stop17h 17m
Deal found 9/26![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 12/88:35 pm -
2 stops14h 58m
Tue 12/1512:28 pm -
1 stop26h 12m
Deal found 9/25![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 12/158:35 pm -
2 stops14h 58m
Sun 12/209:23 pm -
1 stop17h 17m
Deal found 9/26![Multiple Airlines logo]()
$457
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 12/187:00 am -
1 stop24h 05m
Tue 12/228:10 am -
1 stop30h 30m
Deal found 9/25![Multiple Airlines logo]()
$457
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/227:00 am -
1 stop9h 40m
Sun 10/258:04 am -
2 stops27h 01m
Deal found 9/27![Multiple Airlines logo]()
$459
This Mytrip deal was found by Cheapflights users on 9/26. 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 11/108:35 pm -
2 stops21h 41m
Tue 11/177:28 pm -
2 stops20h 57m
Deal found 9/26![Multiple Airlines logo]()
$469
This Mytrip deal was found by Cheapflights users on 9/27. 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 10/264:00 pm -
2 stops19h 22m
Mon 11/26:16 am -
2 stops17h 54m
Deal found 9/27![Multiple Airlines logo]()
$546
This Booking.com deal was found by Cheapflights users on 9/24. 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.
Thu 10/229:05 pm -
3 stops17h 30m
Thu 10/296:16 am -
2 stops18h 54m
Deal found 9/24![Multiple Airlines logo]()
$585
This Mytrip deal was found by Cheapflights users on 9/25. 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 10/245:10 pm -
3 stops30h 33m
Mon 11/26:42 pm -
2 stops21h 43m
Deal found 9/25![Multiple Airlines logo]()
$641
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 September 28, 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 September 28, 2026.
This Porter Airlines deal was found by Cheapflights users on 9/23. 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 11/77:00 am -
1 stop7h 37m
Sat 11/142:50 pm -
1 stop7h 07m
Deal found 9/23![Porter Airlines logo]()
$542
This Mytrip deal was found by Cheapflights users on 9/27. 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 10/264:00 pm -
2 stops19h 22m
Mon 11/212:20 pm -
3 stops28h 05m
Deal found 9/27![Multiple Airlines logo]()
$567
This Delta deal was found by Cheapflights users on 9/27. 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 2/256:35 am -
2 stops11h 57m
Sun 2/286:00 am -
1 stop5h 50m
Deal found 9/27![Delta logo]()
$604
This United Airlines deal was found by Cheapflights users on 9/23. 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 11/182:15 pm -
Nonstop2h 35m
Sun 11/229:35 am -
Nonstop2h 48m
Deal found 9/23![United Airlines logo]()
$676
This FlightHub deal was found by Cheapflights users on 9/25. 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.
Sat 10/246:00 am -
2 stops27h 32m
Fri 10/305:31 pm -
1 stop18h 17m
Deal found 9/25![WestJet logo]()
$703
This Porter Airlines deal was found by Cheapflights users on 9/26. 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.
Tue 11/107:00 am -
1 stop7h 37m
Tue 11/172:50 pm -
1 stop7h 07m
Deal found 9/26![Porter Airlines logo]()
$551
This Porter Airlines deal was found by Cheapflights users on 9/26. 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.
Tue 12/157:00 am -
1 stop7h 37m
Tue 12/158:45 pm -
1 stop14h 00m
Deal found 9/26![Porter Airlines logo]()
$587
This United Airlines deal was found by Cheapflights users on 9/26. 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 11/102:15 pm -
Nonstop2h 35m
Tue 11/178:40 am -
1 stop12h 17m
Deal found 9/26![United Airlines logo]()
$687
This FlightHub deal was found by Cheapflights users on 9/27. 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 11/128:35 pm -
2 stops19h 43m
Tue 11/175:29 pm -
1 stop18h 26m
Deal found 9/27![WestJet logo]()
$732
This United Airlines deal was found by Cheapflights users on 9/27. 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 11/122:15 pm -
Nonstop2h 35m
Tue 11/172:30 pm -
1 stop6h 27m
Deal found 9/27![United Airlines logo]()
$687
This Delta deal was found by Cheapflights users on 9/25. 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 12/86:25 am -
1 stop5h 34m
Mon 12/146:00 am -
1 stop8h 40m
Deal found 9/25![Delta logo]()
$768
This oojo deal was found by Cheapflights users on 9/24. 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.
Sat 12/125:24 pm -
1 stop18h 35m
Mon 12/1412:39 pm -
1 stop23h 25m
Deal found 9/24![WestJet logo]()
$752
This United Airlines deal was found by Cheapflights users on 9/26. 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 12/152:15 pm -
Nonstop2h 45m
Sun 12/206:50 am -
1 stop14h 07m
Deal found 9/26![United Airlines logo]()
$687
This Delta deal was found by Cheapflights users on 9/24. 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 stops10h 44m
Mon 1/46:00 am -
1 stop8h 40m
Deal found 9/24![Delta logo]()
$770
This FlightHub deal was found by Cheapflights users on 9/26. 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 10/1311:15 am -
2 stops23h 45m
Sun 10/1811:45 am -
2 stops30h 13m
Deal found 9/26![Porter Airlines logo]()
$746
This FlightHub deal was found by Cheapflights users on 9/27. 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 10/226:15 am -
2 stops9h 59m
Tue 10/275:31 pm -
1 stop18h 17m
Deal found 9/27![WestJet logo]()
$752
This WestJet deal was found by Cheapflights users on 9/26. 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 11/105:32 pm -
1 stop23h 07m
Tue 11/175:29 pm -
1 stop18h 26m
Deal found 9/26![WestJet logo]()
$760
This WestJet deal was found by Cheapflights users on 9/26. 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 12/156:25 am -
1 stop5h 34m
Tue 12/155:30 pm -
1 stop18h 34m
Deal found 9/26![WestJet logo]()
$790
This FlightHub deal was found by Cheapflights users on 9/27. 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 10/226:15 am -
2 stops9h 59m
Sun 10/256:44 pm -
2 stops16h 21m
Deal found 9/27![WestJet logo]()
$828
Last-minute flights from Winnipeg to IllinoisDiscover last-minute flight deals from Winnipeg to Illinois. Data last updated September 28, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Illinois. Data last updated September 28, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 10/219:05 pm -
1 stop19h 35m
Sun 10/2512:20 pm -
1 stop20h 55m
Deal found 9/24![Multiple Airlines logo]()
$499
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 10/215:10 pm -
1 stop17h 50m
Sun 10/256:24 am -
2 stops13h 31m
Deal found 9/24![Multiple Airlines logo]()
$685
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/227:00 am -
1 stop9h 40m
Tue 10/277:15 am -
2 stops34h 10m
Deal found 9/27![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/227:00 am -
1 stop9h 40m
Sun 10/258:04 am -
2 stops27h 01m
Deal found 9/27![Multiple Airlines logo]()
$459
This Booking.com deal was found by Cheapflights users on 9/24. 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.
Thu 10/229:05 pm -
3 stops17h 30m
Thu 10/296:16 am -
2 stops18h 54m
Deal found 9/24![Multiple Airlines logo]()
$585
This Mytrip deal was found by Cheapflights users on 9/27. 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 10/2211:40 am -
2 stops23h 20m
Tue 10/276:42 pm -
2 stops22h 43m
Deal found 9/27![Multiple Airlines logo]()
$660
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 10/237:00 am -
1 stop9h 40m
Mon 10/267:44 pm -
2 stops21h 41m
Deal found 9/25![Multiple Airlines logo]()
$379
This Mytrip deal was found by Cheapflights users on 9/25. 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 10/245:10 pm -
3 stops30h 33m
Mon 11/26:42 pm -
2 stops21h 43m
Deal found 9/25![Multiple Airlines logo]()
$641
This Mytrip deal was found by Cheapflights users on 9/26. 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 10/249:05 pm -
2 stops20h 40m
Sat 10/317:25 am -
2 stops17h 45m
Deal found 9/26![Multiple Airlines logo]()
$691
This FlightHub deal was found by Cheapflights users on 9/25. 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.
Sat 10/246:00 am -
2 stops27h 32m
Fri 10/305:31 pm -
1 stop18h 17m
Deal found 9/25![WestJet logo]()
$703
This Mytrip deal was found by Cheapflights users on 9/27. 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 10/264:00 pm -
2 stops19h 22m
Mon 11/26:16 am -
2 stops17h 54m
Deal found 9/27![Multiple Airlines logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/296:00 am -
2 stops12h 45m
Sun 11/112:20 pm -
1 stop21h 55m
Deal found 9/27![Multiple Airlines logo]()
$482
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 September 28, 2026.
Search for one-way flight options from Winnipeg to Illinois. Find affordable one-way fares based on user searches. Data last updated September 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 10/227:00 am -
1 stop9h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![WestJet logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/117:00 am -
1 stop9h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![WestJet logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 10/316:00 am -
2 stops12h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Multiple Airlines logo]()
$203
This Trip.com deal was found by Cheapflights users on 9/24. 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 10/289:35 pm -
2 stops21h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 10/296:00 am -
2 stops12h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 11/48:35 pm -
2 stops22h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$206
This Trip.com deal was found by Cheapflights users on 9/26. 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.
Tue 11/108:35 pm -
2 stops21h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Multiple Airlines logo]()
$213
This Trip.com deal was found by Cheapflights users on 9/24. 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 10/289:35 pm -
2 stops26h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 11/59:00 am -
2 stops9h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 11/48:35 pm -
2 stops21h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 12/38:35 pm -
2 stops25h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Multiple Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 10/149:05 pm -
1 stop19h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![WestJet logo]()
$219
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 September 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $377 (Kiwi.com) |
One-way from | $191 (Kiwi.com) |
Popular in | January |
Cheapest in | November |
Average price | $565 |
Good round-trip deal | $653 or less |
Good one-way deal | $404 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 September 28, 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 - MDW Chicago Midway
YWGMDW
Winnipeg
Thu 10/29
6:00 am-11:47 pm
2 stops17h 47m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$215
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Thu 11/5
9:00 am-6:05 pm
2 stops9h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$215
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Wed 11/4
8:35 pm-5:47 pm
2 stops21h 12m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$217
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Wed 11/4
7:00 am-2:37 pm
1 stop7h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$225
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Fri 11/6
7:00 am-2:37 pm
1 stop7h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$235
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Tue 11/10
8:35 pm-9:10 pm
3 stops24h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$254
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Tue 11/10
5:00 am-11:22 am
3 stops30h 22m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$312
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Tue 12/15
5:00 am-9:25 am
3 stops28h 25m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$324
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Sat 10/10
4:55 pm-4:40 pm
1 stop23h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$336
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Sat 10/10
11:15 am-2:35 pm
2 stops27h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$348
Showing 1-10 of 37 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
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
What is the cheapest month to book a flight from Winnipeg to Illinois?
Currently, November is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of $491). Flying from Winnipeg to Illinois in October is currently the most expensive (average of $699). 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 September 28, 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 September 28, 2026.
The most flights from YWG to USIL are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Winnipeg to Illinois?
Airfare is below average for this route at the moment.
Winnipeg to Illinois flights typically cost between $756 and $1,338 in October.The cheapest round-trip price found within the last 5 days was $377 on Multiple Airlines (Oct 22-Oct 27).
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 September 28, 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.
Entertainment
7.1
Boarding
7.7
Food
6.7
Comfort
7.3
Overall
7.4
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Entertainment
7.1
Boarding
7.7
Food
6.7
Comfort
7.3
Overall
7.4
Crew
8.1
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 September 28, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated September 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$471 | Average$701 | FlexibilityNo cancel fee | On-time69% |