$172+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Jul 22 — Jul 291
Round-trip
1 adult, Economy
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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 June 22, 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 June 22, 2026.
This Trip.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:15 am
YWG
- ORD
1 stop7h 20m
WestJet
Sun 11/12:20 pm
ORD
- YWG
1 stop7h 20m
WestJet
Deal found 6/18![WestJet logo]()
$291
This oojo deal was found by Cheapflights users on 6/20. 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 9/117:00 am
YWG
- ORD
1 stop9h 40m
WestJet
Sun 9/135:30 pm
ORD
- YWG
1 stop7h 25m
WestJet
Deal found 6/20![WestJet logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 9/117:00 am
YWG
- ORD
1 stop9h 40m
Multiple Airlines
Sun 9/133:20 pm
ORD
- YWG
2 stops26h 38m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 9/137:00 am
YWG
- ORD
1 stop9h 40m
Multiple Airlines
Mon 9/147:00 am
ORD
- YWG
2 stops10h 58m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$345
This oojo deal was found by Cheapflights users on 6/19. 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 9/169:05 pm
YWG
- ORD
1 stop19h 35m
WestJet
Sun 9/205:30 pm
ORD
- YWG
1 stop18h 45m
WestJet
Deal found 6/19![WestJet logo]()
$360
This Mytrip deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1710:45 am
YWG
- ORD
1 stop9h 44m
Multiple Airlines
Sun 7/195:35 pm
ORD
- YWG
2 stops17h 08m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 pm
YWG
- MDW
1 stop15h 35m
Multiple Airlines
Fri 7/173:20 pm
MDW
- YWG
2 stops26h 38m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$370
This oojo deal was found by Cheapflights users on 6/18. 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 8/217:00 am
YWG
- ORD
1 stop9h 40m
WestJet
Mon 8/245:30 pm
ORD
- YWG
1 stop7h 25m
WestJet
Deal found 6/18![WestJet logo]()
$370
This oojo deal was found by Cheapflights users on 6/17. 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 8/117:00 am
YWG
- ORD
1 stop9h 40m
WestJet
Fri 8/145:30 pm
ORD
- YWG
1 stop7h 25m
WestJet
Deal found 6/17![WestJet logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 9/137:00 am
YWG
- ORD
1 stop9h 40m
WestJet
Mon 9/145:30 pm
ORD
- YWG
1 stop7h 25m
WestJet
Deal found 6/18![WestJet logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 8/208:45 pm
YWG
- MDW
1 stop12h 55m
Multiple Airlines
Tue 8/253:15 pm
MDW
- YWG
2 stops21h 00m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/176:05 pm
YWG
- MDW
1 stop15h 35m
Multiple Airlines
Sun 7/193:20 pm
MDW
- YWG
1 stop18h 25m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$416
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 June 22, 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 June 22, 2026.
This United Airlines deal was found by Cheapflights users on 6/20. 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 9/187:00 am
YWG
- STL
1 stop5h 02m
United Airlines
Mon 9/215:30 pm
STL
- YWG
1 stop5h 03m
United Airlines
Deal found 6/20![United Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 6/17. 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 10/53:58 pm
YWG
- STL
1 stop7h 22m
Delta
Wed 10/76:00 am
STL
- YWG
2 stops14h 16m
Delta
Deal found 6/17![Delta logo]()
$482
This United deal was found by Cheapflights users on 6/20. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:56 pm
YWG
- STL
1 stop8h 30m
Multiple Airlines
Mon 7/208:55 am
STL
- YWG
1 stop7h 25m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$506
This Porter Airlines deal was found by Cheapflights users on 6/18. 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
YWG
- ORD
2 stops8h 40m
Porter Airlines
Sun 9/2011:45 am
ORD
- YWG
2 stops30h 13m
Porter Airlines
Deal found 6/18![Porter Airlines logo]()
$507
This Air Canada deal was found by Cheapflights users on 6/17. 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.
Mon 10/52:05 pm
YWG
- STL
1 stop5h 55m
Air Canada
Wed 10/72:40 pm
STL
- YWG
1 stop8h 27m
Air Canada
Deal found 6/17![Air Canada logo]()
$523
This WestJet deal was found by Cheapflights users on 6/18. 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 9/276:15 am
YWG
- STL
2 stops11h 25m
WestJet
Wed 9/3010:00 am
STL
- YWG
2 stops12h 10m
WestJet
Deal found 6/18![WestJet logo]()
$549
This United Airlines deal was found by Cheapflights users on 6/21. 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 7/1712:56 pm
YWG
- STL
1 stop8h 30m
United Airlines
Mon 7/206:00 am
STL
- YWG
1 stop5h 52m
United Airlines
Deal found 6/21![United Airlines logo]()
$498
This United deal was found by Cheapflights users on 6/18. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:00 am
YWG
- STL
1 stop14h 36m
Multiple Airlines
Sat 9/198:55 am
STL
- YWG
1 stop7h 22m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$515
This KAYAK deal was found by Cheapflights users on 6/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:40 am
YWG
- STL
1 stop8h 36m
Delta
Sun 7/58:49 am
STL
- YWG
1 stop8h 02m
Delta
Deal found 6/19![Delta logo]()
$536
This United Airlines deal was found by Cheapflights users on 6/21. 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
YWG
- STL
1 stop11h 51m
United Airlines
Wed 10/79:04 am
STL
- YWG
1 stop13h 29m
United Airlines
Deal found 6/21![United Airlines logo]()
$508
This oojo deal was found by Cheapflights users on 6/20. 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 9/117:00 am
YWG
- MDW
2 stops11h 19m
WestJet
Sun 9/139:20 am
MDW
- YWG
2 stops12h 50m
WestJet
Deal found 6/20![WestJet logo]()
$587
This Porter Airlines deal was found by Cheapflights users on 6/19. 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.
Thu 7/309:20 am
YWG
- ORD
1 stop6h 59m
Porter Airlines
Tue 8/48:37 pm
ORD
- YWG
1 stop23h 17m
Porter Airlines
Deal found 6/19![Porter Airlines logo]()
$588
This Mytrip deal was found by Cheapflights users on 6/21. 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 8/254:15 pm
YWG
- MDW
2 stops17h 30m
Multiple Airlines
Sat 8/296:42 pm
MDW
- YWG
3 stops23h 16m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$572
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:40 am
YWG
- MDW
1 stop6h 40m
Delta
Tue 9/227:01 pm
MDW
- YWG
2 stops16h 55m
Delta
Deal found 6/21![Delta logo]()
$589
This Mytrip deal was found by Cheapflights users on 6/21. 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 7/1311:40 am
YWG
- MDW
2 stops22h 00m
Porter Airlines
Fri 7/173:20 pm
MDW
- YWG
2 stops19h 00m
Porter Airlines
Deal found 6/21![Porter Airlines logo]()
$598
This United Airlines deal was found by Cheapflights users on 6/19. 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 8/37:00 am
YWG
- STL
1 stop8h 46m
United Airlines
Mon 8/109:20 am
STL
- YWG
1 stop13h 18m
United Airlines
Deal found 6/19![United Airlines logo]()
$544
This oojo deal was found by Cheapflights users on 6/17. 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 7/256:15 am
YWG
- MDW
2 stops26h 58m
WestJet
Tue 7/289:54 am
MDW
- YWG
1 stop6h 57m
WestJet
Deal found 6/17![WestJet logo]()
$607
This oojo deal was found by Cheapflights users on 6/20. 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 8/185:42 pm
YWG
- MDW
1 stop24h 19m
WestJet
Mon 8/317:25 pm
MDW
- YWG
1 stop16h 29m
WestJet
Deal found 6/20![WestJet logo]()
$611
This Delta deal was found by Cheapflights users on 6/21. 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 10/138:00 am
YWG
- MDW
1 stop8h 50m
Delta
Mon 10/1912:30 pm
MDW
- YWG
1 stop7h 46m
Delta
Deal found 6/21![Delta logo]()
$622
This KAYAK deal was found by Cheapflights users on 6/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/39:20 am
YWG
- ORD
1 stop6h 59m
Porter Airlines
Sun 7/58:10 am
ORD
- YWG
1 stop7h 09m
Porter Airlines
Deal found 6/16![Porter Airlines logo]()
$624
This United Airlines deal was found by Cheapflights users on 6/21. 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 7/148:15 am
YWG
- ORD
2 stops14h 00m
United Airlines
Fri 7/177:45 pm
ORD
- YWG
2 stops15h 30m
United Airlines
Deal found 6/21![United Airlines logo]()
$619
This Justfly.com deal was found by Cheapflights users on 6/20. 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 8/185:42 pm
YWG
- MDW
1 stop24h 19m
WestJet
Thu 8/201:51 pm
MDW
- YWG
1 stop22h 03m
WestJet
Deal found 6/20![WestJet logo]()
$620
This United Airlines deal was found by Cheapflights users on 6/20. 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 7/168:15 am
YWG
- ORD
2 stops14h 00m
United Airlines
Fri 7/177:45 pm
ORD
- YWG
2 stops15h 30m
United Airlines
Deal found 6/20![United Airlines logo]()
$626
This United Airlines deal was found by Cheapflights users on 6/19. 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 7/172:05 pm
YWG
- ORD
2 stops16h 31m
United Airlines
Fri 7/249:41 pm
ORD
- YWG
2 stops13h 34m
United Airlines
Deal found 6/19![United Airlines logo]()
$655
This United Airlines deal was found by Cheapflights users on 6/20. 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
YWG
- ORD
Nonstop2h 21m
United Airlines
Sun 11/2210:50 am
ORD
- YWG
1 stop9h 58m
United Airlines
Deal found 6/20![United Airlines logo]()
$657
This United Airlines deal was found by Cheapflights users on 6/19. 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 9/212:00 pm
YWG
- ORD
Nonstop2h 35m
United Airlines
Tue 9/229:15 am
ORD
- YWG
Nonstop2h 37m
United Airlines
Deal found 6/19![United Airlines logo]()
$657
This United Airlines deal was found by Cheapflights users on 6/18. 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 7/1812:56 pm
YWG
- ORD
Nonstop2h 34m
United Airlines
Sun 7/199:14 am
ORD
- YWG
Nonstop2h 38m
United Airlines
Deal found 6/18![United Airlines logo]()
$663
Last-minute flights from Winnipeg to IllinoisDiscover last-minute flight deals from Winnipeg to Illinois. Data last updated June 22, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Illinois. Data last updated June 22, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 6/20. 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 7/912:15 pm
YWG
- ORD
1 stop7h 14m
Multiple Airlines
Fri 7/175:30 pm
ORD
- YWG
1 stop7h 25m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$466
This flugladen.de deal was found by Cheapflights users on 6/21. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/910:55 am
YWG
- STL
1 stop7h 47m
Air Canada
Wed 7/158:55 am
STL
- YWG
1 stop7h 25m
Air Canada
Deal found 6/21![Air Canada logo]()
$486
This Trip.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:20 am
YWG
- ORD
1 stop6h 59m
Multiple Airlines
Tue 7/145:30 pm
ORD
- YWG
1 stop7h 25m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$474
This Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 pm
YWG
- MDW
1 stop15h 35m
Multiple Airlines
Fri 7/173:20 pm
MDW
- YWG
2 stops26h 38m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$370
This oojo deal was found by Cheapflights users on 6/21. 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 7/1412:00 pm
YWG
- ORD
1 stop28h 40m
WestJet
Fri 7/175:30 pm
ORD
- YWG
1 stop7h 25m
WestJet
Deal found 6/21![WestJet logo]()
$396
This Mytrip deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1710:45 am
YWG
- ORD
1 stop9h 44m
Multiple Airlines
Sun 7/195:35 pm
ORD
- YWG
2 stops17h 08m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/176:05 pm
YWG
- MDW
1 stop15h 35m
Multiple Airlines
Sun 7/193:20 pm
MDW
- YWG
1 stop18h 25m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$416
This United Airlines deal was found by Cheapflights users on 6/21. 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 7/1712:56 pm
YWG
- STL
1 stop8h 30m
United Airlines
Mon 7/206:00 am
STL
- YWG
1 stop5h 52m
United Airlines
Deal found 6/21![United Airlines logo]()
$498
This United deal was found by Cheapflights users on 6/20. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:56 pm
YWG
- STL
1 stop8h 30m
Multiple Airlines
Mon 7/208:55 am
STL
- YWG
1 stop7h 25m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$506
This Air Canada deal was found by Cheapflights users on 6/20. 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.
Fri 7/172:05 pm
YWG
- STL
1 stop6h 17m
Air Canada
Mon 7/208:55 am
STL
- YWG
1 stop7h 25m
Air Canada
Deal found 6/20![Air Canada logo]()
$508
This Justfly.com deal was found by Cheapflights users on 6/20. 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 7/1710:45 am
YWG
- STL
2 stops22h 46m
WestJet
Mon 7/205:36 pm
STL
- YWG
2 stops28h 04m
WestJet
Deal found 6/20![WestJet logo]()
$523
This Mytrip deal was found by Cheapflights users on 6/18. 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 7/186:15 am
YWG
- ORD
1 stop14h 14m
Multiple Airlines
Sun 7/195:35 pm
ORD
- YWG
2 stops16h 45m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$391
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 June 22, 2026.
Search for one-way flight options from Winnipeg to Illinois. Find affordable one-way fares based on user searches. Data last updated June 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 10/256:15 am
YWG
- ORD
1 stop7h 20m
WestJet
Deal found 6/16![WestJet logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 8/117:00 am
YWG
- ORD
1 stop9h 40m
WestJet
Deal found 6/20![WestJet logo]()
$208
This Justfly.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:00 am
YWG
- ORD
1 stop9h 40m
WestJet
Deal found 6/19![WestJet logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 7/128:50 pm
YWG
- MDW
1 stop12h 50m
Porter Airlines
Deal found 6/21![Porter Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/2011:40 am
YWG
- MDW
2 stops22h 00m
Porter Airlines
Deal found 6/19![Porter Airlines logo]()
$224
This Trip.com deal was found by Cheapflights users on 6/19. 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.
Mon 8/176:05 pm
YWG
- ORD
1 stop14h 25m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 8/106:05 pm
YWG
- ORD
2 stops42h 10m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$237
This Trip.com deal was found by Cheapflights users on 6/20. 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.
Mon 8/1012:00 pm
YWG
- ORD
1 stop28h 40m
WestJet
Deal found 6/20![WestJet logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 8/1011:15 am
YWG
- MDW
2 stops22h 25m
Porter Airlines
Deal found 6/21![Porter Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/126:55 pm
YWG
- STL
3 stops46h 42m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 8/119:05 pm
YWG
- MDW
2 stops12h 46m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$273
This United Airlines deal was found by Cheapflights users on 6/19. 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 7/117:00 am
YWG
- STL
1 stop12h 23m
United Airlines
Deal found 6/19![United Airlines logo]()
$276
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 June 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $291 (Trip.com) |
One-way from | $172 (Kiwi.com) |
Popular in | January |
Cheapest in | October |
Average price | $843 |
Good round-trip deal | $500 or less |
Good one-way deal | $355 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 June 22, 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 9/18
7:00 am-12:02 pm
1 stop5h 02m
Lambert-St Louis
Mon 9/21
5:30 pm-10:33 pm
1 stop5h 03m
$477
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Mon 10/5
3:58 pm-11:20 pm
1 stop7h 22m
Lambert-St Louis
Wed 10/7
6:00 am-8:16 pm
2 stops14h 16m
$482
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Fri 7/17
12:56 pm-9:26 pm
1 stop8h 30m
Lambert-St Louis
Mon 7/20
6:00 am-11:52 am
1 stop5h 52m
$498
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Fri 7/17
12:56 pm-9:26 pm
1 stop8h 30m
Lambert-St Louis
Mon 7/20
8:55 am-4:20 pm
1 stop7h 25m
$506
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Wed 9/16
11:40 am-8:20 pm
2 stops8h 40m
Chicago O'Hare Intl
Sun 9/20
11:45 am-5:58 pm
2 stops30h 13m
$507
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Mon 10/5
8:45 am-8:36 pm
1 stop11h 51m
Lambert-St Louis
Wed 10/7
9:04 am-10:33 pm
1 stop13h 29m
$508
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Fri 9/18
7:00 am-9:36 pm
1 stop14h 36m
Lambert-St Louis
Sat 9/19
8:55 am-4:17 pm
1 stop7h 22m
$515
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Mon 10/5
2:05 pm-8:00 pm
1 stop5h 55m
Lambert-St Louis
Wed 10/7
2:40 pm-11:07 pm
1 stop8h 27m
$523
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Fri 7/3
6:40 am-3:16 pm
1 stop8h 36m
Lambert-St Louis
Sun 7/5
8:49 am-4:51 pm
1 stop8h 02m
$536
WinnipegSt. Louis
YWG - STL
YWGSTL
Winnipeg
Mon 8/3
7:00 am-3:46 pm
1 stop8h 46m
Lambert-St Louis
Mon 8/10
9:20 am-10:38 pm
1 stop13h 18m
$544
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-MDW
YWG-STL
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Winnipeg to Illinois
YWG-USIL
YWG-ORD
YWG-MDW
YWG-STL
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 $447). 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 June 22, 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?
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 June 22, 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
Crew
8.1
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
6.0
GoodGerry,Jan 2026
YVR - DEN
Boarding
7.7
Food
6.6
Comfort
7.3
Crew
8.1
Overall
7.4
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
See prices for flight routes from nearby airports that may be better suited for you.
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 June 22, 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 2,558,603 searches. Data last updated June 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$199 | Average$517 | FlexibilityNo cancel fee | On-time69% |