$167+ 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Oct 26 — Nov 21
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 September 26, 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 September 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
Thu 10/225:30 pm -
1 stop7h 25m
Mon 10/269:35 pm -
2 stops14h 05m
Deal found 9/21![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
Thu 10/225:30 pm -
1 stop7h 25m
Thu 10/297:00 am -
1 stop10h 40m
Deal found 9/21![Multiple Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:20 pm -
1 stop14h 55m
Mon 11/166:55 pm -
1 stop16h 45m
Deal found 9/23![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 10/195:30 pm -
1 stop7h 25m
Tue 10/279:35 pm -
2 stops15h 16m
Deal found 9/21![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:30 pm -
1 stop7h 25m
Sat 10/316:00 am -
2 stops12h 16m
Deal found 9/23![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:30 pm -
1 stop7h 25m
Fri 10/309:35 pm -
2 stops15h 16m
Deal found 9/23![Multiple Airlines logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:30 pm -
1 stop7h 25m
Sun 11/18:35 pm -
2 stops22h 10m
Deal found 9/23![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 10/235:30 pm -
2 stops16h 05m
Tue 10/275:00 am -
1 stop12h 40m
Deal found 9/21![Multiple Airlines logo]()
$395
This Lucky2Go deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:20 pm -
1 stop14h 55m
Sun 11/86:55 pm -
1 stop22h 45m
Deal found 9/23![Multiple Airlines logo]()
$406
This Mytrip deal was found by Cheapflights users on 9/21. 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.
Wed 10/2111:45 am -
1 stop13h 10m
Wed 10/289:35 pm -
2 stops20h 12m
Deal found 9/21![Multiple Airlines logo]()
$434
This Mytrip deal was found by Cheapflights users on 9/21. 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 10/2011:45 am -
1 stop8h 05m
Tue 10/279:35 pm -
2 stops20h 12m
Deal found 9/21![Multiple Airlines logo]()
$441
This Mytrip deal was found by Cheapflights users on 9/21. 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.
Thu 10/2211:45 am -
1 stop13h 10m
Thu 10/299:35 pm -
2 stops20h 12m
Deal found 9/21![Multiple Airlines logo]()
$443
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 September 26, 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 September 26, 2026.
This Mytrip deal was found by Cheapflights users on 9/21. 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.
Wed 10/2111:45 am -
1 stop13h 10m
Wed 10/289:35 pm -
2 stops20h 12m
Deal found 9/21![Multiple Airlines logo]()
$434
This Porter Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/122:50 pm -
1 stop7h 07m
Mon 11/167:00 am -
1 stop7h 37m
Deal found 9/24![Porter Airlines logo]()
$683
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 12/38:04 am -
2 stops8h 30m
Tue 12/86:25 am -
2 stops9h 52m
Deal found 9/22![Delta logo]()
$767
This oojo deal was found by Cheapflights users on 9/21. 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.
Fri 1/151:00 pm -
2 stops11h 44m
Sun 1/178:05 pm -
2 stops16h 28m
Deal found 9/21![WestJet logo]()
$824
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/309:35 am -
Nonstop2h 48m
Tue 12/12:15 pm -
Nonstop2h 45m
Deal found 9/22![United Airlines logo]()
$864
This American Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/235:00 am -
3 stops16h 57m
Mon 12/287:00 am -
3 stops27h 16m
Deal found 9/24![American Airlines logo]()
$1,269
This FlightHub deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/911:45 am -
2 stops30h 13m
Mon 10/127:00 am -
2 stops9h 47m
Deal found 9/24![Multiple Airlines logo]()
$826
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Wed 11/49:35 am -
Nonstop2h 48m
Wed 11/112:15 pm -
Nonstop2h 35m
Deal found 9/21![United Airlines logo]()
$865
This FlightHub deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:00 am -
2 stops17h 55m
Tue 12/85:00 am -
2 stops12h 02m
Deal found 9/25![WestJet logo]()
$870
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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.
Sun 1/241:00 pm -
2 stops10h 34m
Mon 2/16:35 am -
1 stop5h 16m
Deal found 9/22![Delta logo]()
$873
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/289:29 am -
Nonstop2h 54m
Mon 11/22:15 pm -
Nonstop2h 35m
Deal found 9/22![United Airlines logo]()
$886
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 12/310:24 am -
1 stop6h 10m
Sun 12/612:54 pm -
2 stops10h 00m
Deal found 9/22![Delta logo]()
$889
This United deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1810:00 am -
Nonstop2h 52m
Sat 12/268:05 am -
1 stop6h 47m
Deal found 9/23![Multiple Airlines logo]()
$895
This oojo deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1312:27 pm -
1 stop10h 52m
Tue 12/812:54 pm -
1 stop23h 05m
Deal found 9/25![WestJet logo]()
$974
This United Airlines deal was found by Cheapflights users on 9/21. 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 11/249:35 am -
Nonstop2h 48m
Sat 11/282:15 pm -
Nonstop2h 35m
Deal found 9/21![United Airlines logo]()
$886
This Delta deal was found by Cheapflights users on 9/21. 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 11/2412:30 pm -
1 stop4h 12m
Sat 11/2812:45 pm -
1 stop3h 54m
Deal found 9/21![Delta logo]()
$911
This United Airlines deal was found by Cheapflights users on 9/21. 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 12/49:35 am -
Nonstop2h 48m
Mon 12/72:15 pm -
Nonstop2h 45m
Deal found 9/21![United Airlines logo]()
$886
This Expedia deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:24 am -
1 stop6h 10m
Tue 12/86:25 am -
1 stop10h 25m
Deal found 9/22![WestJet logo]()
$1,001
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:29 am -
Nonstop2h 54m
Sun 11/12:15 pm -
Nonstop2h 35m
Deal found 9/25![United Airlines logo]()
$907
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:31 pm -
1 stop5h 48m
Wed 11/116:35 am -
1 stop5h 15m
Deal found 9/23![Delta logo]()
$1,030
This United Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/236:10 am -
1 stop6h 42m
Mon 12/282:15 pm -
1 stop8h 25m
Deal found 9/24![United Airlines logo]()
$933
This United Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:49 am -
2 stops10h 38m
Sat 10/318:40 am -
1 stop12h 32m
Deal found 9/24![United Airlines logo]()
$1,054
Last-minute flights from Illinois to WinnipegDiscover last-minute flight deals from Illinois to Winnipeg. Data last updated September 26, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Winnipeg. Data last updated September 26, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:42 am -
1 stop8h 08m
Tue 10/69:20 am -
1 stop6h 54m
Deal found 9/22![Porter Airlines logo]()
$748
This Justfly.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:03 am -
1 stop7h 17m
Tue 10/67:00 am -
1 stop9h 40m
Deal found 9/23![Multiple Airlines logo]()
$891
This FlightHub deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/28:03 am -
2 stops9h 55m
Tue 10/69:20 am -
1 stop6h 54m
Deal found 9/22![Porter Airlines logo]()
$866
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:25 am -
1 stop6h 43m
Mon 10/58:10 pm -
2 stops43h 10m
Deal found 9/23![Multiple Airlines logo]()
$902
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:30 pm -
1 stop26h 50m
Sun 10/116:00 am -
2 stops24h 34m
Deal found 9/23![Multiple Airlines logo]()
$753
This Justfly.com deal was found by Cheapflights users on 9/21. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:30 pm -
1 stop7h 25m
Fri 10/98:45 pm -
1 stop17h 35m
Deal found 9/21![Multiple Airlines logo]()
$572
This Mytrip deal was found by Cheapflights users on 9/21. 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 10/2011:45 am -
1 stop8h 05m
Tue 10/279:35 pm -
2 stops20h 12m
Deal found 9/21![Multiple Airlines logo]()
$441
This Mytrip deal was found by Cheapflights users on 9/21. 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.
Wed 10/2111:45 am -
1 stop13h 10m
Wed 10/289:35 pm -
2 stops20h 12m
Deal found 9/21![Multiple Airlines logo]()
$434
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/213:20 pm -
1 stop9h 35m
Tue 10/279:35 pm -
2 stops20h 12m
Deal found 9/24![Multiple Airlines logo]()
$482
This Mytrip deal was found by Cheapflights users on 9/21. 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.
Thu 10/2211:45 am -
1 stop13h 10m
Thu 10/299:35 pm -
2 stops20h 12m
Deal found 9/21![Multiple Airlines logo]()
$443
This Mytrip deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:42 pm -
2 stops22h 43m
Sun 11/18:35 pm -
2 stops21h 12m
Deal found 9/25![Multiple Airlines logo]()
$451
This Mytrip deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:42 pm -
2 stops22h 43m
Mon 11/28:35 pm -
2 stops21h 12m
Deal found 9/23![Multiple Airlines logo]()
$485
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 September 26, 2026.
Search for one-way flight options from Illinois to Winnipeg. Find affordable one-way fares based on user searches. Data last updated September 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 10/55:30 pm -
1 stop7h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![WestJet logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
Tue 10/276:20 pm -
1 stop25h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 12/612:20 pm -
2 stops28h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$174
This Trip.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:50 pm -
2 stops28h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
Sat 10/243:20 pm -
2 stops23h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$178
This Trip.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:16 am -
2 stops17h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:50 pm -
2 stops29h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:42 pm -
2 stops22h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
Thu 10/297:50 pm -
2 stops21h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 11/66:20 pm -
2 stops23h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Porter Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:15 am -
2 stops16h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:42 pm -
2 stops21h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$214
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 September 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $361 (Kiwi.com) |
One-way from | $167 (Kiwi.com) |
Popular in | August |
Cheapest in | February |
Average price | $512 |
Good round-trip deal | $876 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 7,457,451 searches. Data last updated September 26, 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
Tue 10/27
6:20 pm-5:25 pm
2 stops23h 05m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$173
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Sat 10/24
3:20 pm-2:20 pm
2 stops23h 00m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$178
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 10/30
7:50 pm-1:10 am
2 stops29h 20m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 11/6
6:20 pm-6:10 pm
2 stops23h 50m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$202
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Sat 11/7
6:42 pm-4:25 pm
2 stops21h 43m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Fri 11/6
6:42 pm-12:10 am
2 stops29h 28m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$217
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 10/14
8:30 am-12:55 am
3 stops40h 25m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$222
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 11/30
7:55 am-4:25 pm
2 stops32h 30m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$228
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 2/10
6:00 am-4:25 pm
2 stops34h 25m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$241
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Wed 2/10
1:18 pm-4:25 pm
2 stops27h 07m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$241
Showing 1-10 of 41 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, October is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $479). 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 September 26, 2026.
One of the essential ways to save on airfare from Illinois to Winnipeg is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 51% 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 September 26, 2026.
The most flights from USIL to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Illinois to Winnipeg?
Airfare is typical for this route at the moment.
Illinois to Winnipeg flights typically cost between $248 and $1,062 in October.The cheapest round-trip price found within the last 5 days was $361 on Multiple Airlines (Oct 22-Oct 26).
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 September 26, 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 September 26, 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 7,457,451 searches. Data last updated September 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$222 | Average$454 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$362 | Average$762 | FlexibilityNo cancel fee | On-time69% |