$163+ Cheap flights from Illinois to Winnipeg (YWG)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Sep 9 — Sep 161
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Winnipeg with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Illinois to Winnipeg
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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 August 10, 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 August 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:45 am -
1 stop9h 00m
Sun 9/1311:15 am -
2 stops23h 45m
Deal found 8/8![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:20 pm -
1 stop9h 35m
Sun 9/2711:15 am -
2 stops23h 45m
Deal found 8/7![Multiple Airlines logo]()
$334
This Mytrip deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/209:50 am -
1 stop15h 05m
Sun 9/276:05 pm -
1 stop14h 55m
Deal found 8/6![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:11 am -
2 stops17h 44m
Fri 9/257:00 am -
1 stop9h 40m
Deal found 8/7![Multiple Airlines logo]()
$378
This Mytrip deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:45 am -
1 stop8h 04m
Sun 9/138:45 pm -
1 stop14h 15m
Deal found 8/8![Porter Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:11 am -
2 stops17h 44m
Sat 10/107:10 pm -
1 stop21h 30m
Deal found 8/8![Multiple Airlines logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:30 pm -
1 stop7h 25m
Mon 9/77:00 am -
1 stop9h 40m
Deal found 8/9![WestJet logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:30 pm -
1 stop7h 25m
Mon 9/77:00 am -
1 stop9h 40m
Deal found 8/9![WestJet logo]()
$410
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:30 pm -
1 stop7h 25m
Mon 10/125:00 pm -
1 stop12h 42m
Deal found 8/7![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:30 pm -
1 stop7h 25m
Sun 10/117:00 am -
1 stop9h 40m
Deal found 8/7![WestJet logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:30 pm -
1 stop7h 25m
Sun 10/117:00 am -
1 stop9h 40m
Deal found 8/7![WestJet logo]()
$417
This Justfly.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:30 pm -
1 stop7h 25m
Sat 9/57:00 am -
1 stop9h 40m
Deal found 8/8![WestJet logo]()
$418
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 August 10, 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 August 10, 2026.
This Trip.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:30 pm -
1 stop7h 25m
Sat 10/107:10 pm -
1 stop21h 30m
Deal found 8/8![WestJet logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:30 pm -
1 stop7h 25m
Sat 10/109:05 pm -
2 stops35h 10m
Deal found 8/8![Multiple Airlines logo]()
$445
This Porter Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:42 am -
1 stop8h 12m
Sun 9/279:20 am -
1 stop6h 58m
Deal found 8/6![Porter Airlines logo]()
$618
This Air Canada deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/41:57 pm -
1 stop7h 17m
Wed 11/1112:45 pm -
1 stop7h 13m
Deal found 8/9![Air Canada logo]()
$681
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/41:27 pm -
2 stops9h 52m
Wed 11/116:35 am -
1 stop5h 15m
Deal found 8/10![Delta logo]()
$755
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:30 pm -
1 stop7h 25m
Mon 9/79:25 am -
2 stops37h 43m
Deal found 8/9![Multiple Airlines logo]()
$522
This oojo deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:23 pm -
2 stops22h 02m
Fri 9/119:05 pm -
2 stops15h 27m
Deal found 8/7![WestJet logo]()
$594
This Porter Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:06 am -
1 stop7h 13m
Tue 10/134:15 pm -
1 stop16h 24m
Deal found 8/7![Porter Airlines logo]()
$644
This FlightHub deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:30 am -
2 stops7h 55m
Thu 9/36:40 am -
1 stop3h 43m
Deal found 8/6![WestJet logo]()
$616
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:30 am -
1 stop4h 53m
Sat 11/217:15 am -
1 stop8h 11m
Deal found 8/7![Air Canada logo]()
$692
This Porter Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:03 am -
2 stops26h 40m
Wed 9/3011:40 am -
2 stops8h 40m
Deal found 8/9![Porter Airlines logo]()
$653
This Mytrip deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:30 pm -
2 stops21h 10m
Sat 10/109:05 pm -
3 stops19h 39m
Deal found 8/8![Multiple Airlines logo]()
$678
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:59 am -
1 stop6h 53m
Sat 9/56:40 am -
2 stops10h 19m
Deal found 8/9![Delta logo]()
$755
This FlightHub deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:37 pm -
2 stops17h 58m
Sat 11/215:35 pm -
1 stop5h 48m
Deal found 8/8![WestJet logo]()
$641
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:59 am -
1 stop5h 09m
Sat 10/108:00 am -
1 stop3h 47m
Deal found 8/8![Delta logo]()
$759
This Porter Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/203:20 pm -
2 stops26h 38m
Sun 9/274:15 pm -
2 stops18h 45m
Deal found 8/6![Porter Airlines logo]()
$707
This oojo deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:00 am -
2 stops11h 15m
Mon 9/77:00 am -
2 stops9h 40m
Deal found 8/9![WestJet logo]()
$661
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:59 am -
1 stop5h 09m
Sat 10/108:00 am -
1 stop3h 47m
Deal found 8/8![Delta logo]()
$759
This oojo deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/109:30 am -
2 stops9h 45m
Fri 12/115:35 pm -
1 stop23h 04m
Deal found 8/7![WestJet logo]()
$665
This oojo deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:23 pm -
2 stops24h 02m
Thu 9/106:05 pm -
2 stops21h 09m
Deal found 8/6![WestJet logo]()
$676
This oojo deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:48 am -
2 stops9h 57m
Sat 10/105:40 pm -
1 stop18h 07m
Deal found 8/9![WestJet logo]()
$718
This oojo deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/19:59 am -
2 stops12h 11m
Mon 9/79:05 pm -
2 stops18h 19m
Deal found 8/9![WestJet logo]()
$745
This oojo deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/59:29 am -
2 stops7h 46m
Wed 10/76:15 am -
2 stops10h 04m
Deal found 8/5![WestJet logo]()
$767
This oojo deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:25 pm -
2 stops11h 30m
Mon 8/317:10 pm -
2 stops14h 49m
Deal found 8/5![WestJet logo]()
$768
Last-minute flights from Illinois to WinnipegDiscover last-minute flight deals from Illinois to Winnipeg. Data last updated August 10, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Winnipeg. Data last updated August 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:30 pm -
1 stop7h 25m
Thu 9/37:00 am -
1 stop9h 40m
Deal found 8/5![WestJet logo]()
$429
This Trip.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:30 pm -
1 stop7h 25m
Thu 9/39:05 pm -
1 stop19h 35m
Deal found 8/7![WestJet logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:30 pm -
1 stop7h 25m
Mon 9/77:00 am -
1 stop9h 40m
Deal found 8/9![WestJet logo]()
$410
This Justfly.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:30 pm -
1 stop7h 25m
Sat 9/57:00 am -
1 stop9h 40m
Deal found 8/8![WestJet logo]()
$418
This Trip.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:30 pm -
1 stop7h 25m
Wed 9/97:10 pm -
1 stop21h 30m
Deal found 8/7![WestJet logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:30 pm -
1 stop7h 25m
Mon 9/77:00 am -
1 stop9h 40m
Deal found 8/9![WestJet logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:45 am -
1 stop9h 00m
Sun 9/1311:15 am -
2 stops23h 45m
Deal found 8/8![Multiple Airlines logo]()
$320
This Mytrip deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:45 am -
1 stop8h 04m
Sun 9/138:45 pm -
1 stop14h 15m
Deal found 8/8![Porter Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:11 am -
2 stops17h 44m
Fri 9/257:00 am -
1 stop9h 40m
Deal found 8/7![Multiple Airlines logo]()
$378
This Mytrip deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/209:50 am -
1 stop15h 05m
Sun 9/276:05 pm -
1 stop14h 55m
Deal found 8/6![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:20 pm -
1 stop9h 35m
Sun 9/2711:15 am -
2 stops23h 45m
Deal found 8/7![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:30 pm -
1 stop7h 25m
Sun 9/277:00 am -
1 stop9h 40m
Deal found 8/7![WestJet logo]()
$435
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 August 10, 2026.
Search for one-way flight options from Illinois to Winnipeg. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
This Trip.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:40 pm -
1 stop24h 05m
Deal found 8/9![Multiple Airlines logo]()
$163
This Flightnetwork deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:30 pm -
1 stop7h 25m
Deal found 8/7![WestJet logo]()
$176
This Mytrip deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:30 pm -
1 stop7h 25m
Deal found 8/6![WestJet logo]()
$186
This FlightHub deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:30 pm -
1 stop7h 25m
Deal found 8/7![WestJet logo]()
$189
This Trip.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:30 pm -
1 stop7h 25m
Deal found 8/8![WestJet logo]()
$190
This Mytrip deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/135:30 pm -
1 stop23h 55m
Deal found 8/7![WestJet logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:10 pm -
1 stop15h 05m
Deal found 8/5![Multiple Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:20 am -
2 stops15h 50m
Deal found 8/8![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:28 pm -
2 stops19h 57m
Deal found 8/9![Multiple Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:05 am -
3 stops29h 05m
Deal found 8/7![Multiple Airlines logo]()
$256
This FlightHub deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:15 am -
2 stops15h 25m
Deal found 8/7![WestJet logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/223:20 pm -
3 stops42h 00m
Deal found 8/9![Multiple Airlines logo]()
$268
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 August 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $320 (Kiwi.com) |
One-way from | $163 (Trip.com) |
Popular in | August |
Cheapest in | February |
Average price | $1,256 |
Good round-trip deal | $1,046 or less |
Good one-way deal | $337 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 2,558,603 searches. Data last updated August 10, 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
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 10/2
5:30 pm-12:55 am
1 stop7h 25m
Winnipeg
Sat 10/10
7:10 pm-4:40 pm
1 stop21h 30m
$403
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 10/2
5:30 pm-12:55 am
1 stop7h 25m
Winnipeg
Sat 10/10
9:05 pm-8:15 am
2 stops35h 10m
$445
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 9/3
5:30 pm-12:55 am
1 stop7h 25m
Winnipeg
Mon 9/7
9:25 am-11:08 pm
2 stops37h 43m
$522
St. LouisWinnipeg
STL Lambert-St Louis - YWG Winnipeg
STLYWG
Lambert-St Louis
Fri 9/4
5:23 pm-3:25 pm
2 stops22h 02m
Winnipeg
Fri 9/11
9:05 pm-12:32 pm
2 stops15h 27m
$594
St. LouisWinnipeg
STL Lambert-St Louis - YWG Winnipeg
STLYWG
Lambert-St Louis
Thu 8/27
6:30 am-2:25 pm
2 stops7h 55m
Winnipeg
Thu 9/3
6:40 am-10:23 am
1 stop3h 43m
$616
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 9/23
11:42 am-7:54 pm
1 stop8h 12m
Winnipeg
Sun 9/27
9:20 am-4:18 pm
1 stop6h 58m
$618
St. LouisWinnipeg
STL Lambert-St Louis - YWG Winnipeg
STLYWG
Lambert-St Louis
Fri 11/13
5:37 pm-11:35 am
2 stops17h 58m
Winnipeg
Sat 11/21
5:35 pm-11:23 pm
1 stop5h 48m
$641
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 10/7
8:06 am-3:19 pm
1 stop7h 13m
Winnipeg
Tue 10/13
4:15 pm-8:39 am
1 stop16h 24m
$644
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 9/23
8:03 am-10:43 am
2 stops26h 40m
Winnipeg
Wed 9/30
11:40 am-8:20 pm
2 stops8h 40m
$653
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 9/3
6:00 am-5:15 pm
2 stops11h 15m
Winnipeg
Mon 9/7
7:00 am-4:40 pm
2 stops9h 40m
$661
Showing 1-10 of 44 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
STL-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
STL-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 $435). 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 August 10, 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 morning tend to be the most expensive. A flight at noon could potentially save you up to 43% on airfare.
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
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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 August 10, 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 August 10, 2026.
Top 2 airlines flying from Illinois to Winnipeg
Discover the top 2 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 2,558,603 searches. Data last updated August 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$208 | Average$405 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$362 | Average$762 | FlexibilityNo cancel fee | On-time69% |