$177+ 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 6/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
May 30 — Jun 61
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 April 30, 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 April 30, 2026.
This oojo deal was found by Cheapflights users on 4/28. 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.
Thu 5/289:05 pm
YWG
- ORD
1 stop19h 35m
WestJet
Thu 6/45:30 pm
ORD
- YWG
1 stop7h 25m
WestJet
Deal found 4/28![WestJet logo]()
$267
This oojo deal was found by Cheapflights users on 4/29. 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 6/107:00 am
YWG
- ORD
1 stop9h 40m
WestJet
Mon 6/155:30 pm
ORD
- YWG
1 stop7h 25m
WestJet
Deal found 4/29![WestJet logo]()
$274
This oojo deal was found by Cheapflights users on 4/29. 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 9/157:00 am
YWG
- ORD
1 stop9h 40m
WestJet
Fri 9/185:30 pm
ORD
- YWG
1 stop7h 25m
WestJet
Deal found 4/29![WestJet logo]()
$282
This FlightHub deal was found by Cheapflights users on 4/25. 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.
Fri 8/217:00 am
YWG
- ORD
1 stop9h 40m
WestJet
Mon 8/245:30 pm
ORD
- YWG
1 stop7h 25m
WestJet
Deal found 4/25![WestJet logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 5/267:00 am
YWG
- ORD
1 stop9h 40m
Multiple Airlines
Tue 6/29:37 pm
ORD
- YWG
2 stops22h 38m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$336
This FlightHub deal was found by Cheapflights users on 4/25. 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.
Fri 8/217:00 am
YWG
- ORD
1 stop9h 40m
WestJet
Sun 8/235:30 pm
ORD
- YWG
1 stop7h 25m
WestJet
Deal found 4/25![WestJet logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
Thu 8/207:00 am
YWG
- ORD
1 stop9h 40m
WestJet
Sat 8/225:30 pm
ORD
- YWG
1 stop7h 25m
WestJet
Deal found 4/25![WestJet logo]()
$347
This WestJet deal was found by Cheapflights users on 4/25. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:00 am
YWG
- ORD
1 stop9h 40m
WestJet
Wed 8/265:30 pm
ORD
- YWG
1 stop7h 25m
WestJet
Deal found 4/25![WestJet logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Fri 5/296:00 am
YWG
- ORD
1 stop10h 40m
Multiple Airlines
Tue 6/29:37 pm
ORD
- YWG
2 stops22h 38m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$369
This Justfly.com deal was found by Cheapflights users on 4/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:41 pm
YWG
- STL
1 stop16h 51m
WestJet
Tue 6/96:30 am
STL
- YWG
2 stops18h 25m
WestJet
Deal found 4/27![WestJet logo]()
$382
This Justfly.com deal was found by Cheapflights users on 4/26. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:00 am
YWG
- STL
2 stops9h 46m
WestJet
Tue 6/25:36 pm
STL
- YWG
2 stops28h 34m
WestJet
Deal found 4/26![WestJet logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/289:05 pm
YWG
- MDW
2 stops14h 04m
Multiple Airlines
Thu 6/43:20 pm
MDW
- YWG
1 stop18h 25m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$391
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 April 30, 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 April 30, 2026.
This Justfly.com deal was found by Cheapflights users on 4/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:41 pm
YWG
- STL
1 stop16h 51m
WestJet
Tue 6/96:30 am
STL
- YWG
2 stops18h 25m
WestJet
Deal found 4/27![WestJet logo]()
$382
This Delta deal was found by Cheapflights users on 4/28. 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 5/236:40 am
YWG
- MDW
2 stops14h 29m
Delta
Wed 5/275:12 pm
MDW
- YWG
2 stops21h 43m
Delta
Deal found 4/28![Delta logo]()
$468
This Mytrip deal was found by Cheapflights users on 4/28. 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 6/44:15 pm
YWG
- MDW
2 stops17h 20m
Porter Airlines
Sun 6/710:15 am
MDW
- YWG
2 stops7h 43m
Porter Airlines
Deal found 4/28![Porter Airlines logo]()
$541
This Mytrip deal was found by Cheapflights users on 4/28. 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 6/207:00 am
YWG
- ORD
3 stops23h 02m
Multiple Airlines
Sun 6/285:30 pm
ORD
- YWG
1 stop21h 55m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$556
This United Airlines deal was found by Cheapflights users on 4/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/237:00 am
YWG
- ORD
Nonstop2h 34m
United Airlines
Mon 7/275:00 am
ORD
- YWG
1 stop15h 57m
United Airlines
Deal found 4/25![United Airlines logo]()
$631
This WestJet deal was found by Cheapflights users on 4/28. 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 9/2210:45 am
YWG
- STL
2 stops9h 46m
WestJet
Sat 9/266:30 am
STL
- YWG
1 stop5h 04m
WestJet
Deal found 4/28![WestJet logo]()
$406
This WestJet deal was found by Cheapflights users on 4/26. 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.
Mon 8/106:15 am
YWG
- STL
2 stops9h 42m
WestJet
Tue 8/118:50 am
STL
- YWG
1 stop26h 44m
WestJet
Deal found 4/26![WestJet logo]()
$406
This WestJet deal was found by Cheapflights users on 4/29. 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.
Fri 6/196:00 am
YWG
- STL
2 stops28h 28m
WestJet
Sun 8/95:19 pm
STL
- YWG
2 stops22h 06m
WestJet
Deal found 4/29![WestJet logo]()
$413
This Delta deal was found by Cheapflights users on 4/30. 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 6/235:41 pm
YWG
- MDW
2 stops15h 33m
Delta
Tue 6/306:58 pm
MDW
- YWG
2 stops20h 06m
Delta
Deal found 4/30![Delta logo]()
$506
This Porter Airlines deal was found by Cheapflights users on 4/26. 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 6/169:20 am
YWG
- ORD
1 stop6h 58m
Porter Airlines
Sat 6/208:08 am
ORD
- YWG
1 stop7h 11m
Porter Airlines
Deal found 4/26![Porter Airlines logo]()
$556
This WestJet deal was found by Cheapflights users on 4/29. 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 9/279:05 pm
YWG
- STL
2 stops20h 57m
WestJet
Wed 9/305:30 pm
STL
- YWG
2 stops21h 55m
WestJet
Deal found 4/29![WestJet logo]()
$422
This Delta deal was found by Cheapflights users on 4/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:40 am
YWG
- MDW
2 stops15h 37m
Delta
Sat 6/206:00 am
MDW
- YWG
2 stops17h 29m
Delta
Deal found 4/26![Delta logo]()
$517
This Porter Airlines deal was found by Cheapflights users on 4/26. 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.
Fri 6/129:20 am
YWG
- ORD
1 stop6h 58m
Porter Airlines
Wed 6/178:08 am
ORD
- YWG
2 stops9h 50m
Porter Airlines
Deal found 4/26![Porter Airlines logo]()
$563
This Justfly.com deal was found by Cheapflights users on 4/26. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2411:55 am
YWG
- STL
1 stop11h 26m
WestJet
Sun 5/316:21 am
STL
- YWG
2 stops15h 19m
WestJet
Deal found 4/26![WestJet logo]()
$426
This United Airlines deal was found by Cheapflights users on 4/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/212:00 pm
YWG
- ORD
Nonstop2h 34m
United Airlines
Thu 7/237:55 pm
ORD
- YWG
Nonstop2h 38m
United Airlines
Deal found 4/25![United Airlines logo]()
$631
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Tue 7/147:00 am
YWG
- ORD
Nonstop2h 34m
United Airlines
Sun 7/265:00 am
ORD
- YWG
1 stop15h 57m
United Airlines
Deal found 4/27![United Airlines logo]()
$632
This Delta deal was found by Cheapflights users on 4/27. 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.
Wed 9/236:40 am
YWG
- ORD
1 stop8h 18m
Delta
Sat 9/265:20 pm
ORD
- YWG
1 stop6h 07m
Delta
Deal found 4/27![Delta logo]()
$612
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Sat 6/137:00 am
YWG
- ORD
Nonstop2h 34m
United Airlines
Wed 6/175:00 am
ORD
- YWG
1 stop15h 57m
United Airlines
Deal found 4/26![United Airlines logo]()
$632
This oojo deal was found by Cheapflights users on 4/27. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/257:00 am
YWG
- MDW
2 stops11h 05m
WestJet
Sat 8/299:20 am
MDW
- YWG
2 stops12h 50m
WestJet
Deal found 4/27![WestJet logo]()
$508
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Sun 6/147:00 am
YWG
- ORD
Nonstop2h 34m
United Airlines
Mon 6/227:55 pm
ORD
- YWG
Nonstop2h 38m
United Airlines
Deal found 4/27![United Airlines logo]()
$632
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Fri 5/297:00 am
YWG
- ORD
Nonstop2h 34m
United Airlines
Tue 6/27:05 am
ORD
- YWG
1 stop13h 52m
United Airlines
Deal found 4/26![United Airlines logo]()
$632
This Justfly.com deal was found by Cheapflights users on 4/25. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:00 am
YWG
- MDW
2 stops26h 08m
WestJet
Thu 7/239:20 am
MDW
- YWG
2 stops15h 35m
WestJet
Deal found 4/25![WestJet logo]()
$540
This FlightHub deal was found by Cheapflights users on 4/28. 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 6/2312:46 pm
YWG
- MDW
1 stop5h 32m
WestJet
Tue 6/301:49 pm
MDW
- YWG
1 stop27h 02m
WestJet
Deal found 4/28![WestJet logo]()
$555
This oojo deal was found by Cheapflights users on 4/30. 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 5/224:55 pm
YWG
- ORD
1 stop23h 45m
WestJet
Sun 5/315:30 pm
ORD
- YWG
1 stop26h 45m
WestJet
Deal found 4/30![WestJet logo]()
$556
This WestJet deal was found by Cheapflights users on 4/29. 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.
Sat 5/237:00 am
YWG
- MDW
2 stops10h 56m
WestJet
Wed 5/279:23 am
MDW
- YWG
1 stop25h 31m
WestJet
Deal found 4/29![WestJet logo]()
$569
This FlightHub deal was found by Cheapflights users on 4/27. 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.
Tue 6/235:41 pm
YWG
- ORD
1 stop3h 44m
WestJet
Tue 6/306:30 am
ORD
- YWG
1 stop5h 26m
WestJet
Deal found 4/27![WestJet logo]()
$595
Last-minute flights from Winnipeg to IllinoisDiscover last-minute flight deals from Winnipeg to Illinois. Data last updated April 30, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Illinois. Data last updated April 30, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 4/27. 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.
Wed 5/66:00 am
YWG
- ORD
2 stops15h 57m
WestJet
Fri 5/82:00 pm
ORD
- YWG
2 stops10h 55m
WestJet
Deal found 4/27![WestJet logo]()
$759
This oojo deal was found by Cheapflights users on 4/25. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:00 am
YWG
- MDW
2 stops10h 56m
WestJet
Wed 5/279:23 am
MDW
- YWG
2 stops23h 57m
WestJet
Deal found 4/25![WestJet logo]()
$556
This oojo deal was found by Cheapflights users on 4/29. 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 5/227:00 am
YWG
- MDW
2 stops10h 56m
WestJet
Sun 5/317:13 pm
MDW
- YWG
2 stops22h 02m
WestJet
Deal found 4/29![WestJet logo]()
$623
This Delta deal was found by Cheapflights users on 4/28. 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 5/236:40 am
YWG
- MDW
2 stops14h 29m
Delta
Wed 5/275:12 pm
MDW
- YWG
2 stops21h 43m
Delta
Deal found 4/28![Delta logo]()
$468
This Justfly.com deal was found by Cheapflights users on 4/25. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:41 pm
YWG
- MDW
1 stop24h 15m
WestJet
Sat 5/309:23 am
MDW
- YWG
1 stop14h 03m
WestJet
Deal found 4/25![WestJet logo]()
$536
This WestJet deal was found by Cheapflights users on 4/29. 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.
Sat 5/237:00 am
YWG
- MDW
2 stops10h 56m
WestJet
Wed 5/279:23 am
MDW
- YWG
1 stop25h 31m
WestJet
Deal found 4/29![WestJet logo]()
$569
This Justfly.com deal was found by Cheapflights users on 4/26. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2411:55 am
YWG
- STL
1 stop11h 26m
WestJet
Sun 5/316:21 am
STL
- YWG
2 stops15h 19m
WestJet
Deal found 4/26![WestJet logo]()
$426
This Justfly.com deal was found by Cheapflights users on 4/26. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:00 am
YWG
- STL
2 stops9h 46m
WestJet
Tue 6/25:36 pm
STL
- YWG
2 stops28h 34m
WestJet
Deal found 4/26![WestJet logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/289:05 pm
YWG
- MDW
2 stops14h 04m
Multiple Airlines
Thu 6/43:20 pm
MDW
- YWG
1 stop18h 25m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$391
This FlightHub deal was found by Cheapflights users on 4/26. 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.
Thu 5/286:40 am
YWG
- STL
1 stop3h 52m
WestJet
Sun 5/318:53 am
STL
- YWG
2 stops12h 47m
WestJet
Deal found 4/26![WestJet logo]()
$434
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/288:45 pm
YWG
- MDW
1 stop17h 50m
Porter Airlines
Thu 6/410:15 am
MDW
- YWG
1 stop9h 34m
Porter Airlines
Deal found 4/28![Porter Airlines logo]()
$459
This oojo deal was found by Cheapflights users on 4/28. 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.
Thu 5/286:15 am
YWG
- MDW
2 stops12h 18m
WestJet
Thu 6/49:23 am
MDW
- YWG
2 stops12h 17m
WestJet
Deal found 4/28![WestJet logo]()
$546
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 April 30, 2026.
Search for one-way flight options from Winnipeg to Illinois. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
This oojo deal was found by Cheapflights users on 4/28. 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.
Mon 8/317:00 am
YWG
- ORD
1 stop9h 40m
WestJet
Deal found 4/28![WestJet logo]()
$186
This Trip.com deal was found by Cheapflights users on 4/29. 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.
Thu 6/47:10 pm
YWG
- ORD
1 stop21h 30m
WestJet
Deal found 4/29![WestJet logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Wed 6/106:00 am
YWG
- ORD
2 stops18h 48m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 6/2011:15 am
YWG
- MDW
2 stops22h 25m
Porter Airlines
Deal found 4/28![Porter Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 6/144:25 pm
YWG
- MDW
1 stop22h 10m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 6/124:15 pm
YWG
- MDW
2 stops17h 20m
Porter Airlines
Deal found 4/28![Porter Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 6/44:15 pm
YWG
- MDW
2 stops22h 20m
Porter Airlines
Deal found 4/29![Porter Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 8/259:05 pm
YWG
- MDW
2 stops25h 06m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 6/49:05 pm
YWG
- ORD
2 stops34h 50m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Wed 6/109:05 pm
YWG
- MDW
3 stops42h 10m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$226
This WestJet deal was found by Cheapflights users on 4/29. 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.
Sat 6/136:40 am
YWG
- STL
1 stop15h 24m
WestJet
Deal found 4/29![WestJet logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 6/136:00 am
YWG
- ORD
2 stops14h 43m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$230
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 April 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $267 (oojo) |
One-way from | $186 (oojo) |
Popular in | March |
Cheapest in | October |
Average price | $505 |
Good round-trip deal | $528 or less |
Good one-way deal | $232 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 April 30, 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
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Fri 6/5
5:41 pm-10:32 am
1 stop16h 51m
Lambert-St Louis
Tue 6/9
6:30 am-12:55 am
2 stops18h 25m
$382
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Tue 9/22
10:45 am-8:31 pm
2 stops9h 46m
Lambert-St Louis
Sat 9/26
6:30 am-11:34 am
1 stop5h 04m
$406
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Mon 8/10
6:15 am-3:57 pm
2 stops9h 42m
Lambert-St Louis
Tue 8/11
8:50 am-11:34 am
1 stop26h 44m
$406
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Fri 6/19
6:00 am-10:28 am
2 stops28h 28m
Lambert-St Louis
Sun 8/9
5:19 pm-3:25 pm
2 stops22h 06m
$413
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Sun 9/27
9:05 pm-6:02 pm
2 stops20h 57m
Lambert-St Louis
Wed 9/30
5:30 pm-3:25 pm
2 stops21h 55m
$422
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Sun 5/24
11:55 am-11:21 pm
1 stop11h 26m
Lambert-St Louis
Sun 5/31
6:21 am-9:40 pm
2 stops15h 19m
$426
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Sat 5/23
6:40 am-9:09 pm
2 stops14h 29m
Chicago Midway
Wed 5/27
5:12 pm-2:55 pm
2 stops21h 43m
$468
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Tue 6/23
5:41 pm-9:14 am
2 stops15h 33m
Chicago Midway
Tue 6/30
6:58 pm-3:04 pm
2 stops20h 06m
$506
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Tue 8/25
7:00 am-6:05 pm
2 stops11h 05m
Chicago Midway
Sat 8/29
9:20 am-10:10 pm
2 stops12h 50m
$508
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Tue 6/16
6:40 am-10:17 pm
2 stops15h 37m
Chicago Midway
Sat 6/20
6:00 am-11:29 pm
2 stops17h 29m
$517
Showing 1-10 of 48 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-STL
YWG-MDW
YWG-ORD
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-STL
YWG-MDW
YWG-ORD
How far ahead should I book a flight from Winnipeg to Illinois?
To ensure you get the cheapest price possible for a flight from Winnipeg to Illinois, you should look to book at least 77 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Winnipeg to Illinois?
Currently, October is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of $80). Flying from Winnipeg to Illinois in January is currently the most expensive (average of $445). 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 April 30, 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 April 30, 2026.
The most flights from YWG to USIL are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Winnipeg to Illinois?
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 April 30, 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
Food
6.6
Comfort
7.3
Overall
7.4
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
6.0
GoodGerry,Jan 2026
YVR - DEN
Boarding
7.7
Food
6.6
Comfort
7.3
Overall
7.4
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
6.0
GoodGerry,Jan 2026
YVR - DEN
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.
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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 April 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 April 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$199 | Average$517 | FlexibilityNo cancel fee | On-time69% |