$138+ Cheap flights from Chicago (CHI) 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Sep 19 — Sep 261
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Winnipeg with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Chicago to WinnipegExplore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2026.
Explore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2026.
This Justfly.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:30 pm -
1 stop7h 25m
Sun 10/117:00 am -
1 stop9h 40m
Deal found 8/19![WestJet logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 9/295:30 pm -
1 stop7h 25m
Tue 10/67:00 am -
1 stop9h 40m
Deal found 8/15![WestJet logo]()
$313
This Justfly.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:30 pm -
1 stop7h 25m
Sat 9/57:00 am -
1 stop9h 40m
Deal found 8/20![WestJet logo]()
$316
This FlightHub deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 10/155:30 pm -
1 stop7h 25m
Sun 10/187:00 am -
1 stop9h 40m
Deal found 8/15![WestJet logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:04 am -
2 stops16h 51m
Fri 10/237:00 am -
1 stop9h 40m
Deal found 8/17![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 9/296:20 am -
2 stops15h 50m
Tue 10/67:00 am -
1 stop9h 40m
Deal found 8/15![Multiple Airlines logo]()
$352
This Kissandfly.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:30 pm -
1 stop26h 45m
Sun 9/207:00 am -
1 stop9h 40m
Deal found 8/17![WestJet logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/115:30 pm -
1 stop7h 25m
Thu 10/227:00 am -
1 stop9h 40m
Deal found 8/17![WestJet logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:30 pm -
1 stop7h 25m
Thu 9/246:00 am -
2 stops18h 23m
Deal found 8/16![Multiple Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 10/158:04 am -
2 stops16h 51m
Sun 10/187:00 am -
1 stop9h 40m
Deal found 8/15![Multiple Airlines logo]()
$364
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:30 pm -
1 stop7h 25m
Sat 10/104:55 pm -
1 stop23h 45m
Deal found 8/20![WestJet logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:30 pm -
1 stop7h 25m
Mon 9/216:00 am -
2 stops18h 23m
Deal found 8/19![Multiple Airlines logo]()
$368
Best flights from Chicago to WinnipegDiscover carefully curated flight deals from Chicago to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 20, 2026.
Discover carefully curated flight deals from Chicago to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 20, 2026.
This Justfly.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:30 pm -
1 stop7h 25m
Sat 9/57:00 am -
1 stop9h 40m
Deal found 8/20![WestJet logo]()
$316
This Mytrip deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 10/155:30 pm -
2 stops15h 50m
Sun 10/1810:30 pm -
2 stops20h 08m
Deal found 8/15![Multiple Airlines logo]()
$557
This FlightHub deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:06 am -
1 stop7h 13m
Tue 10/209:20 am -
1 stop6h 59m
Deal found 8/15![Porter Airlines logo]()
$578
This Air Canada deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:54 pm -
Nonstop2h 39m
Tue 9/85:00 am -
1 stop8h 23m
Deal found 8/18![Air Canada logo]()
$771
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:01 am -
1 stop9h 52m
Sat 10/246:40 am -
2 stops11h 20m
Deal found 8/17![Delta logo]()
$824
This Trip.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:30 pm -
1 stop7h 25m
Sun 9/277:00 am -
1 stop9h 40m
Deal found 8/18![WestJet logo]()
$478
This Porter Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:45 am -
1 stop8h 09m
Wed 10/219:20 am -
1 stop6h 59m
Deal found 8/17![Porter Airlines logo]()
$629
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:30 pm -
2 stops16h 05m
Sat 10/104:15 pm -
2 stops24h 25m
Deal found 8/20![WestJet logo]()
$586
This Porter Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2811:42 am -
1 stop8h 07m
Tue 9/299:20 am -
1 stop10h 10m
Deal found 8/19![Porter Airlines logo]()
$636
This United deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/189:15 am -
Nonstop2h 37m
Sun 9/205:00 am -
1 stop8h 23m
Deal found 8/16![Multiple Airlines logo]()
$816
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1610:01 am -
1 stop9h 52m
Sat 10/246:40 am -
2 stops11h 20m
Deal found 8/17![Delta logo]()
$839
This Porter Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:20 pm -
2 stops26h 38m
Mon 9/2811:15 am -
2 stops27h 20m
Deal found 8/16![Porter Airlines logo]()
$705
This Gotogate deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3010:00 am -
Nonstop2h 37m
Wed 10/77:00 am -
Nonstop2h 35m
Deal found 8/16![Air Canada logo]()
$865
This Mytrip deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/173:20 pm -
2 stops22h 55m
Sun 9/207:10 pm -
3 stops19h 25m
Deal found 8/19![Multiple Airlines logo]()
$823
This oojo deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:44 am -
2 stops14h 26m
Mon 11/28:35 pm -
2 stops15h 38m
Deal found 8/20![WestJet logo]()
$786
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:59 am -
1 stop5h 09m
Sat 9/56:40 am -
2 stops10h 19m
Deal found 8/20![Delta logo]()
$896
This Porter Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/132:50 pm -
1 stop24h 29m
Thu 10/229:20 am -
1 stop6h 59m
Deal found 8/17![Porter Airlines logo]()
$765
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub 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 10/107:00 am -
2 stops11h 00m
Deal found 8/20![WestJet logo]()
$802
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:59 am -
1 stop6h 55m
Wed 10/78:00 am -
1 stop3h 47m
Deal found 8/16![Delta logo]()
$933
This oojo deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:29 am -
2 stops15h 26m
Tue 10/136:40 am -
1 stop10h 07m
Deal found 8/16![WestJet logo]()
$813
This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 9/297:13 pm -
1 stop4h 17m
Tue 10/612:38 pm -
1 stop4h 09m
Deal found 8/15![Delta logo]()
$933
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:27 pm -
1 stop7h 26m
Wed 11/116:35 am -
2 stops11h 29m
Deal found 8/17![Delta logo]()
$957
This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 10/1412:27 pm -
1 stop7h 26m
Tue 10/2012:38 pm -
1 stop4h 09m
Deal found 8/15![Delta logo]()
$965
Last-minute flights from Chicago to WinnipegDiscover last-minute flight deals from Chicago to Winnipeg. Data last updated August 20, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Winnipeg. Data last updated August 20, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:30 pm -
1 stop7h 25m
Sat 9/57:00 am -
1 stop9h 40m
Deal found 8/20![WestJet logo]()
$316
This FlightHub deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 9/45:30 pm -
1 stop7h 25m
Tue 9/89:20 am -
1 stop6h 59m
Deal found 8/15![Multiple Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:30 pm -
1 stop7h 25m
Fri 9/187:55 pm -
2 stops22h 32m
Deal found 8/19![Multiple Airlines logo]()
$370
This Priceline deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:30 pm -
1 stop7h 25m
Fri 9/186:00 am -
1 stop10h 40m
Deal found 8/19![WestJet logo]()
$376
This Kissandfly.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:30 pm -
1 stop26h 45m
Sun 9/207:00 am -
1 stop9h 40m
Deal found 8/17![WestJet logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:30 pm -
1 stop7h 25m
Mon 9/216:00 am -
2 stops18h 23m
Deal found 8/19![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:30 pm -
1 stop7h 25m
Fri 9/256:00 am -
2 stops18h 23m
Deal found 8/19![Multiple Airlines logo]()
$381
This Mytrip deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:20 pm -
1 stop9h 35m
Sun 9/206:15 am -
1 stop8h 20m
Deal found 8/19![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:30 pm -
1 stop7h 25m
Thu 9/246:00 am -
2 stops18h 23m
Deal found 8/16![Multiple Airlines logo]()
$363
This oojo deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 9/2511:45 am -
2 stops30h 13m
Mon 9/284:15 pm -
2 stops22h 20m
Deal found 8/15![Porter Airlines logo]()
$614
This Kiwi.com deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 9/295:30 pm -
1 stop7h 25m
Tue 10/67:00 am -
1 stop9h 40m
Deal found 8/15![WestJet logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 9/296:20 am -
2 stops15h 50m
Tue 10/67:00 am -
1 stop9h 40m
Deal found 8/15![Multiple Airlines logo]()
$352
One-way flights from Chicago to WinnipegSearch for one-way flight options from Chicago to Winnipeg. Find affordable one-way fares based on user searches. Data last updated August 20, 2026.
Search for one-way flight options from Chicago to Winnipeg. Find affordable one-way fares based on user searches. Data last updated August 20, 2026.
This FlightHub deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:30 pm -
1 stop7h 25m
Deal found 8/17![WestJet logo]()
$138
This Trip.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:30 pm -
1 stop7h 25m
Deal found 8/16![WestJet logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:30 pm -
1 stop7h 25m
Deal found 8/19![WestJet logo]()
$147
This FlightHub deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:30 pm -
1 stop7h 25m
Deal found 8/16![WestJet logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:04 am -
2 stops16h 51m
Deal found 8/17![Multiple Airlines logo]()
$163
This Trip.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:15 pm -
1 stop19h 30m
Deal found 8/18![Multiple Airlines logo]()
$171
This Flightnetwork deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:30 pm -
1 stop7h 25m
Deal found 8/17![WestJet logo]()
$173
This Trip.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:30 pm -
1 stop18h 45m
Deal found 8/17![WestJet logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:01 pm -
3 stops23h 59m
Deal found 8/17![Multiple Airlines logo]()
$186
This WestJet deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/115:30 pm -
1 stop7h 25m
Deal found 8/17![WestJet logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 9/306:25 am -
3 stops42h 30m
Deal found 8/15![Multiple Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:15 am -
2 stops15h 55m
Deal found 8/17![Multiple Airlines logo]()
$217
Find flight deals from Chicago to Winnipeg
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $304 (Justfly.com) |
One-way from | $138 (FlightHub) |
Popular in | August |
Cheapest in | February |
Average price | $1,256 |
Good round-trip deal | $1,042 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 August 20, 2026.
Use the filters below to find and compare flights from Chicago 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
Wed 9/2
5:30 pm-12:55 am
1 stop7h 25m
Winnipeg
Sat 9/5
7:00 am-4:40 pm
1 stop9h 40m
$316
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 9/25
5:30 pm-12:55 am
1 stop7h 25m
Winnipeg
Sun 9/27
7:00 am-4:40 pm
1 stop9h 40m
$478
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 10/15
5:30 pm-9:20 am
2 stops15h 50m
Winnipeg
Sun 10/18
10:30 pm-6:38 pm
2 stops20h 08m
$557
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 10/14
8:06 am-3:19 pm
1 stop7h 13m
Winnipeg
Tue 10/20
9:20 am-4:19 pm
1 stop6h 59m
$578
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 10/1
5:30 pm-9:35 am
2 stops16h 05m
Winnipeg
Sat 10/10
4:15 pm-4:40 pm
2 stops24h 25m
$586
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 10/14
11:45 am-7:54 pm
1 stop8h 09m
Winnipeg
Wed 10/21
9:20 am-4:19 pm
1 stop6h 59m
$629
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 9/28
11:42 am-7:49 pm
1 stop8h 07m
Winnipeg
Tue 9/29
9:20 am-7:30 pm
1 stop10h 10m
$636
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Fri 9/25
3:20 pm-5:58 pm
2 stops26h 38m
Winnipeg
Mon 9/28
11:15 am-2:35 pm
2 stops27h 20m
$705
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Tue 10/13
2:50 pm-3:19 pm
1 stop24h 29m
Winnipeg
Thu 10/22
9:20 am-4:19 pm
1 stop6h 59m
$765
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 9/4
7:54 pm-10:33 pm
Nonstop2h 39m
Winnipeg
Tue 9/8
5:00 am-1:23 pm
1 stop8h 23m
$771
Showing 1-10 of 42 resultsSorted by cheapest first
Compare providers for flights from Chicago to Winnipeg
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Winnipeg in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Winnipeg flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Winnipeg
Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Chicago with our price prediction graph.
CHI-YWG
ORD-YWG
MDW-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 Chicago to Winnipeg
CHI-YWG
ORD-YWG
MDW-YWG
What is the cheapest month to book a flight from Chicago to Winnipeg?
Currently, September is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $435). Flying from Chicago 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 CHI to YWG?
Find hourly flight availability from Chicago 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 20, 2026.
One of the essential ways to save on airfare from Chicago 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.
Weekly flight availability from Chicago to Winnipeg
Explore weekly flight availability from Chicago 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 August 20, 2026.
The most flights from CHI to YWG are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
Reviews of airlines servicing Winnipeg
Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated August 20, 2026.
Read reviews from past customers who have flown United Airlines from Chicago to Winnipeg. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Food
6.7
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Overall
7.4
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Crew
8.1
Food
6.7
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Overall
7.4
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago 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
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Chicago and Winnipeg flights
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Top 2 airlines flying from Chicago to Winnipeg
Discover the top 2 airlines that operate flights from Chicago 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 August 20, 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% |