$181+ Cheap flights from Illinois to Winnipeg (YWG)
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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Dec 13 — Dec 201
Round-trip
1 adult, Economy
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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 Illinois to WinnipegExplore the most affordable flight options available from Illinois to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2026.
Explore the most affordable flight options available from Illinois to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/13. Clicking the “Pick Dates” 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 12/126:20 pm -
1 stop14h 55m
Mon 12/149:35 pm -
2 stops17h 55m
Deal found 11/13![Multiple Airlines logo]()
$410
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:29 pm -
2 stops17h 56m
Sun 12/67:55 pm -
1 stop16h 39m
Deal found 11/9![Multiple Airlines logo]()
$441
This Kiwi.com deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1110:29 pm -
2 stops17h 56m
Sun 12/136:25 am -
1 stop6h 19m
Deal found 11/11![Multiple Airlines logo]()
$473
This Mytrip deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:02 pm -
2 stops23h 23m
Sun 12/69:35 pm -
2 stops19h 31m
Deal found 11/9![Multiple Airlines logo]()
$508
This VIAZA deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:05 am -
2 stops16h 39m
Thu 11/196:15 am -
1 stop10h 23m
Deal found 11/8![Air Canada logo]()
$510
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/205:58 am -
2 stops34h 27m
Mon 12/289:05 pm -
1 stop15h 29m
Deal found 11/9![Multiple Airlines logo]()
$511
This FlightHub deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:59 am -
2 stops14h 11m
Sun 12/69:35 pm -
2 stops20h 31m
Deal found 11/9![WestJet logo]()
$514
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/241:11 pm -
1 stop24h 29m
Thu 12/314:00 pm -
2 stops21h 03m
Deal found 11/9![Multiple Airlines logo]()
$606
This Mytrip deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:02 pm -
2 stops23h 23m
Sun 12/137:55 pm -
2 stops14h 42m
Deal found 11/10![Multiple Airlines logo]()
$696
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/206:43 am -
1 stop30h 57m
Mon 12/289:35 pm -
2 stops15h 35m
Deal found 11/9![Multiple Airlines logo]()
$698
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/231:11 pm -
2 stops34h 59m
Wed 12/307:00 am -
1 stop18h 01m
Deal found 11/9![Multiple Airlines logo]()
$712
This Kiwi.com deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/271:11 pm -
1 stop24h 29m
Sun 1/39:05 pm -
2 stops23h 25m
Deal found 11/12![Multiple Airlines logo]()
$739
Best flights from Illinois to WinnipegDiscover carefully curated flight deals from Illinois to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 13, 2026.
Discover carefully curated flight deals from Illinois to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 13, 2026.
This FlightHub deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/212:20 pm -
2 stops29h 51m
Tue 4/69:35 pm -
2 stops20h 57m
Deal found 11/12![Multiple Airlines logo]()
$626
This Porter Airlines deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/1111:45 am -
1 stop10h 14m
Fri 1/156:54 am -
1 stop7h 16m
Deal found 11/12![Porter Airlines logo]()
$660
This KAYAK deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/219:56 am -
1 stop5h 57m
Fri 1/227:00 am -
1 stop28h 04m
Deal found 11/10![WestJet logo]()
$731
This Air Canada deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/204:30 pm -
1 stop7h 54m
Sat 1/238:00 am -
Nonstop2h 45m
Deal found 11/10![Air Canada logo]()
$866
This KAYAK deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/179:38 am -
2 stops10h 12m
Fri 1/227:35 pm -
2 stops21h 47m
Deal found 11/10![Delta logo]()
$874
This United Airlines deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/29:15 am -
Nonstop2h 24m
Tue 4/62:15 pm -
Nonstop2h 21m
Deal found 11/12![United Airlines logo]()
$886
This Mytrip deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1110:29 am -
3 stops22h 46m
Sun 12/137:35 pm -
2 stops16h 59m
Deal found 11/8![Multiple Airlines logo]()
$648
This Flysmarter deal was found by Cheapflights users on 11/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/122:50 pm -
1 stop7h 07m
Mon 12/143:15 pm -
Nonstop2h 45m
Deal found 11/13![Multiple Airlines logo]()
$663
This Porter Airlines deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1412:20 pm -
2 stops29h 51m
Tue 7/139:35 am -
1 stop6h 44m
Deal found 11/11![Porter Airlines logo]()
$763
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:30 pm -
1 stop17h 01m
Sun 12/1312:22 pm -
1 stop5h 28m
Deal found 11/8![WestJet logo]()
$800
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/231:11 pm -
2 stops34h 59m
Wed 12/307:00 am -
1 stop18h 01m
Deal found 11/9![Multiple Airlines logo]()
$712
This KAYAK deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/1410:47 am -
1 stop26h 53m
Sat 1/1612:24 pm -
1 stop5h 29m
Deal found 11/10![Delta logo]()
$874
This United Airlines deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/113:50 pm -
Nonstop2h 38m
Fri 1/158:00 am -
Nonstop2h 45m
Deal found 11/11![United Airlines logo]()
$886
This WestJet deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:39 pm -
1 stop21h 52m
Wed 12/96:00 am -
2 stops29h 28m
Deal found 11/10![WestJet logo]()
$845
This KAYAK deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/211:41 pm -
2 stops11h 03m
Fri 1/227:15 am -
2 stops11h 45m
Deal found 11/10![Delta logo]()
$880
This United Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/273:50 pm -
Nonstop2h 38m
Fri 1/298:00 am -
Nonstop2h 45m
Deal found 11/10![United Airlines logo]()
$886
This United Airlines deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/216:30 am -
1 stop11h 58m
Mon 1/258:00 am -
1 stop14h 44m
Deal found 11/12![United Airlines logo]()
$911
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:30 pm -
1 stop6h 09m
Sun 12/136:25 am -
1 stop6h 34m
Deal found 11/10![Delta logo]()
$911
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/206:43 am -
1 stop30h 57m
Mon 12/287:00 am -
1 stop30h 10m
Deal found 11/9![Multiple Airlines logo]()
$829
This FlightHub deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/215:13 pm -
2 stops26h 37m
Mon 1/259:05 pm -
2 stops20h 23m
Deal found 11/12![WestJet logo]()
$987
This KAYAK deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/251:41 pm -
2 stops11h 03m
Tue 1/267:15 am -
2 stops11h 45m
Deal found 11/12![Delta logo]()
$923
This Mytrip deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2311:05 am -
3 stops24h 15m
Wed 12/307:00 am -
1 stop16h 47m
Deal found 11/9![Multiple Airlines logo]()
$880
This United deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/273:35 pm -
Nonstop2h 51m
Tue 3/91:45 pm -
1 stop7h 13m
Deal found 11/12![Multiple Airlines logo]()
$885
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:30 pm -
1 stop5h 14m
Thu 12/3112:22 pm -
1 stop6h 02m
Deal found 11/9![Delta logo]()
$1,030
Last-minute flights from Illinois to WinnipegDiscover last-minute flight deals from Illinois to Winnipeg. Data last updated November 13, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Winnipeg. Data last updated November 13, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:29 pm -
2 stops17h 56m
Sun 12/67:55 pm -
1 stop16h 39m
Deal found 11/9![Multiple Airlines logo]()
$441
This Mytrip deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:02 pm -
2 stops23h 23m
Sun 12/69:35 pm -
2 stops19h 31m
Deal found 11/9![Multiple Airlines logo]()
$508
This FlightHub deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:59 am -
2 stops14h 11m
Sun 12/69:35 pm -
2 stops20h 31m
Deal found 11/9![WestJet logo]()
$514
This Kiwi.com deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1110:29 pm -
2 stops17h 56m
Sun 12/136:25 am -
1 stop6h 19m
Deal found 11/11![Multiple Airlines logo]()
$473
This Mytrip deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:02 pm -
2 stops23h 23m
Sun 12/137:55 pm -
2 stops14h 42m
Deal found 11/10![Multiple Airlines logo]()
$696
This Kiwi.com deal was found by Cheapflights users on 11/13. Clicking the “Pick Dates” 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 12/126:20 pm -
1 stop14h 55m
Mon 12/149:35 pm -
2 stops17h 55m
Deal found 11/13![Multiple Airlines logo]()
$410
This oojo deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1210:24 am -
1 stop24h 07m
Sun 12/139:05 pm -
2 stops21h 56m
Deal found 11/8![WestJet logo]()
$778
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/205:58 am -
2 stops34h 27m
Mon 12/289:05 pm -
1 stop15h 29m
Deal found 11/9![Multiple Airlines logo]()
$511
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/206:43 am -
1 stop30h 57m
Mon 12/289:35 pm -
2 stops15h 35m
Deal found 11/9![Multiple Airlines logo]()
$698
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/231:11 pm -
2 stops34h 59m
Wed 12/307:00 am -
1 stop18h 01m
Deal found 11/9![Multiple Airlines logo]()
$712
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/241:11 pm -
1 stop24h 29m
Thu 12/314:00 pm -
2 stops21h 03m
Deal found 11/9![Multiple Airlines logo]()
$606
This Kiwi.com deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/271:11 pm -
1 stop24h 29m
Sun 1/39:05 pm -
2 stops23h 25m
Deal found 11/12![Multiple Airlines logo]()
$739
One-way flights from Illinois to WinnipegSearch for one-way flight options from Illinois to Winnipeg. Find affordable one-way fares based on user searches. Data last updated November 13, 2026.
Search for one-way flight options from Illinois to Winnipeg. Find affordable one-way fares based on user searches. Data last updated November 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/296:00 am -
2 stops18h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:28 pm -
2 stops35h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Multiple Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/36:00 am -
2 stops34h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/66:00 am -
2 stops18h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/26:00 am -
2 stops34h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1010:29 pm -
2 stops17h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/105:02 pm -
2 stops23h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Multiple Airlines logo]()
$190
This Trip.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/15:32 pm -
2 stops30h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$193
This Trip.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/11:18 pm -
2 stops27h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/76:20 pm -
1 stop14h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/46:00 am -
2 stops18h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/86:00 am -
2 stops18h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Multiple Airlines logo]()
$200
Find flight deals from Illinois to Winnipeg
Keep the following information in mind while searching for Illinois to Winnipeg flight deals. Data was last updated November 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $351 (Kiwi.com) |
One-way from | $181 (Kiwi.com) |
Popular in | August |
Cheapest in | February |
Average price | $450 |
Good round-trip deal | $542 or less |
Good one-way deal | $316 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 13, 2026.
Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Sat 12/12
12:28 pm-12:10 am
2 stops35h 42m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$182
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Thu 12/10
5:02 pm-4:25 pm
2 stops23h 23m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$190
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 12/4
7:08 pm-4:25 pm
2 stops21h 17m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$203
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 11/30
12:15 pm-6:14 pm
2 stops29h 59m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$254
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Tue 2/2
10:51 am-12:10 am
2 stops13h 19m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$262
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Sat 12/12
5:24 pm-1:40 pm
3 stops44h 16m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$269
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 12/10
10:29 pm-7:50 pm
3 stops21h 21m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$276
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 12/4
5:33 pm-11:39 pm
1 stop6h 06m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 11/30
9:20 pm-12:10 am
3 stops26h 50m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$280
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Sat 12/26
8:30 pm-12:00 pm
2 stops39h 30m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$290
Showing 1-10 of 45 resultsSorted by cheapest first
Best time to book a flight from Illinois to Winnipeg
Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Illinois with our price prediction graph.
ORD-YWG
MDW-YWG
MLI-YWG
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 Illinois to Winnipeg
USIL-YWG
ORD-YWG
MDW-YWG
MLI-YWG
What is the cheapest month to book a flight from Illinois to Winnipeg?
Currently, September is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $512). Flying from Illinois to Winnipeg in January is currently the most expensive (average of $1,231). 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 IL to YWG?
Find hourly flight availability from Illinois to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2026.
One of the essential ways to save on airfare from Illinois to Winnipeg is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 32% on airfare.
Weekly flight availability from Illinois to Winnipeg
Explore weekly flight availability from Illinois to Winnipeg. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 13, 2026.
The most flights from USIL to YWG are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).
Related info for your journey
Find useful and relevant information for your journey from Illinois to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Winnipeg?
Book flights to Winnipeg if you plan to visit one of these locationsPortage la Prairie
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Illinois to Winnipeg
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Winnipeg by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Illinois to Winnipeg by cabin class
Find flights from Illinois to Winnipeg, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Winnipeg flights
Browse other Illinois and Winnipeg flight options. Last updated on November 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Winnipeg
Explore flights to Winnipeg departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 13, 2026.
Top 3 airlines flying from Illinois to Winnipeg
Discover the top 3 airlines that operate flights from Illinois to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$208 | Average$454 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$291 | Average$865 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$322 | Average$780 | FlexibilityNo cancel fee | On-time67% |