$152+ Cheap flights from Winnipeg (YWG) to Chicago (CHI)
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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from Winnipeg to Chicago 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 Winnipeg to ChicagoExplore the most affordable flight options available from Winnipeg to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
Explore the most affordable flight options available from Winnipeg to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 9/67:00 am -
1 stop9h 40m
Fri 9/115:30 pm -
1 stop7h 25m
Deal found 8/21![WestJet logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 10/167:00 am -
1 stop9h 40m
Mon 10/195:30 pm -
1 stop7h 25m
Deal found 8/21![WestJet logo]()
$282
This Booking.com deal was found by Cheapflights users on 8/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am -
1 stop9h 40m
Mon 10/195:30 pm -
1 stop7h 25m
Deal found 8/21![WestJet logo]()
$290
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:00 am -
1 stop9h 40m
Sun 9/135:30 pm -
1 stop7h 25m
Deal found 8/19![WestJet logo]()
$296
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:10 pm -
1 stop21h 30m
Tue 10/65:30 pm -
1 stop7h 25m
Deal found 8/19![WestJet logo]()
$315
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:55 pm -
1 stop25h 45m
Sun 9/205:30 pm -
1 stop7h 25m
Deal found 8/19![WestJet logo]()
$322
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/174:55 pm -
1 stop23h 45m
Thu 9/245:30 pm -
1 stop7h 25m
Deal found 8/19![WestJet logo]()
$328
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 9/176:15 am -
1 stop13h 33m
Sun 9/205:30 pm -
1 stop7h 25m
Deal found 8/17![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 10/167:00 am -
1 stop9h 40m
Mon 10/198:04 am -
2 stops16h 51m
Deal found 8/21![Multiple Airlines logo]()
$332
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 9/117:55 pm -
1 stop15h 05m
Mon 9/143:20 pm -
1 stop9h 35m
Deal found 8/19![Multiple Airlines logo]()
$335
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:10 pm -
1 stop14h 50m
Sun 9/273:20 pm -
1 stop9h 35m
Deal found 8/18![Multiple Airlines logo]()
$345
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:15 am -
1 stop8h 20m
Sun 9/203:20 pm -
1 stop9h 35m
Deal found 8/17![Multiple Airlines logo]()
$385
Best flights from Winnipeg to ChicagoDiscover carefully curated flight deals from Winnipeg to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
Discover carefully curated flight deals from Winnipeg to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:15 am -
1 stop8h 20m
Sun 9/203:20 pm -
1 stop9h 35m
Deal found 8/17![Multiple Airlines logo]()
$386
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.
Wed 9/99:20 am -
1 stop6h 58m
Sat 9/128:03 am -
1 stop7h 16m
Deal found 8/16![Porter Airlines logo]()
$515
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 9/95:44 pm -
2 stops15h 23m
Sat 9/126:05 am -
2 stops17h 25m
Deal found 8/20![Delta logo]()
$562
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:05 pm -
2 stops19h 53m
Mon 10/1212:30 pm -
2 stops9h 10m
Deal found 8/16![WestJet logo]()
$615
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:15 pm -
Nonstop2h 35m
Sun 11/229:35 am -
Nonstop2h 48m
Deal found 8/19![United Airlines logo]()
$699
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.
Fri 10/96:40 am -
1 stop10h 58m
Mon 10/1211:41 am -
2 stops9h 59m
Deal found 8/16![Multiple Airlines logo]()
$649
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.
Tue 10/136:00 am -
2 stops12h 00m
Sun 10/181:27 pm -
2 stops11h 28m
Deal found 8/16![WestJet logo]()
$662
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:00 pm -
Nonstop2h 35m
Thu 10/86:00 am -
1 stop14h 57m
Deal found 8/17![United Airlines logo]()
$700
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.
Thu 10/112:41 pm -
1 stop5h 38m
Thu 10/812:27 pm -
1 stop7h 26m
Deal found 8/17![Delta logo]()
$728
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:00 am -
2 stops13h 00m
Sun 11/15:31 pm -
1 stop26h 22m
Deal found 8/18![WestJet logo]()
$664
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/122:15 pm -
Nonstop2h 35m
Tue 11/179:35 am -
Nonstop2h 48m
Deal found 8/16![United Airlines logo]()
$700
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.
Thu 9/1711:40 am -
2 stops26h 55m
Sun 9/203:20 pm -
2 stops26h 38m
Deal found 8/19![Porter Airlines logo]()
$785
This WestJet 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:40 am -
1 stop11h 39m
Sat 9/125:37 pm -
2 stops31h 18m
Deal found 8/20![WestJet logo]()
$688
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:00 am -
Nonstop2h 35m
Tue 10/610:55 am -
1 stop10h 02m
Deal found 8/18![United Airlines logo]()
$700
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:40 am -
1 stop6h 40m
Tue 10/65:31 pm -
1 stop5h 48m
Deal found 8/18![Delta logo]()
$842
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:00 pm -
Nonstop2h 35m
Sun 9/209:15 am -
Nonstop2h 37m
Deal found 8/17![United Airlines logo]()
$700
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.
Thu 9/1711:40 am -
2 stops23h 20m
Thu 9/243:20 pm -
2 stops19h 23m
Deal found 8/19![Porter Airlines logo]()
$864
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:15 pm -
Nonstop2h 35m
Sun 11/19:35 am -
Nonstop2h 48m
Deal found 8/18![United Airlines logo]()
$700
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 9/29:05 pm -
2 stops12h 54m
Sat 9/59:24 am -
2 stops15h 31m
Deal found 8/20![WestJet logo]()
$808
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:00 am -
Nonstop2h 35m
Sun 9/277:54 pm -
Nonstop2h 39m
Deal found 8/20![United Airlines logo]()
$701
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/242:15 pm -
Nonstop2h 47m
Sat 1/239:15 am -
Nonstop2h 24m
Deal found 8/20![United Airlines logo]()
$701
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.
Thu 8/277:00 am -
2 stops11h 33m
Sun 8/309:24 am -
2 stops7h 51m
Deal found 8/20![WestJet logo]()
$890
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.
Fri 10/97:10 pm -
2 stops22h 50m
Mon 10/125:31 pm -
1 stop5h 48m
Deal found 8/16![WestJet logo]()
$906
Last-minute flights from Winnipeg to ChicagoDiscover last-minute flight deals from Winnipeg to Chicago. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Chicago. Data last updated August 21, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 9/67:00 am -
1 stop9h 40m
Fri 9/115:30 pm -
1 stop7h 25m
Deal found 8/21![WestJet logo]()
$280
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:00 am -
1 stop9h 40m
Sun 9/135:30 pm -
1 stop7h 25m
Deal found 8/19![WestJet logo]()
$296
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 9/117:55 pm -
1 stop15h 05m
Mon 9/143:20 pm -
1 stop9h 35m
Deal found 8/19![Multiple Airlines logo]()
$335
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:55 pm -
1 stop25h 45m
Sun 9/205:30 pm -
1 stop7h 25m
Deal found 8/19![WestJet logo]()
$322
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/174:55 pm -
1 stop23h 45m
Thu 9/245:30 pm -
1 stop7h 25m
Deal found 8/19![WestJet logo]()
$328
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 9/176:15 am -
1 stop13h 33m
Sun 9/205:30 pm -
1 stop7h 25m
Deal found 8/17![Multiple Airlines logo]()
$331
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:15 am -
1 stop8h 20m
Sun 9/203:20 pm -
1 stop9h 35m
Deal found 8/17![Multiple Airlines logo]()
$385
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:20 am -
1 stop6h 58m
Sun 9/205:30 pm -
1 stop7h 25m
Deal found 8/20![Multiple Airlines logo]()
$360
This flugladen.de deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:20 am -
1 stop6h 58m
Sun 9/275:30 pm -
1 stop7h 25m
Deal found 8/21![Multiple Airlines logo]()
$356
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:10 pm -
1 stop14h 50m
Sun 9/273:20 pm -
1 stop9h 35m
Deal found 8/18![Multiple Airlines logo]()
$345
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:05 pm -
1 stop16h 55m
Sun 10/43:20 pm -
1 stop9h 35m
Deal found 8/20![Multiple Airlines logo]()
$412
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 9/309:20 am -
1 stop6h 58m
Tue 10/65:30 pm -
1 stop7h 25m
Deal found 8/20![Multiple Airlines logo]()
$361
One-way flights from Winnipeg to ChicagoSearch for one-way flight options from Winnipeg to Chicago. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
Search for one-way flight options from Winnipeg to Chicago. Find affordable one-way fares based on user searches. Data last updated August 21, 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 8/317:00 am -
1 stop9h 40m
Deal found 8/17![WestJet logo]()
$152
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:00 am -
1 stop9h 40m
Deal found 8/20![WestJet logo]()
$170
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.
Fri 10/167:00 am -
1 stop9h 40m
Deal found 8/17![WestJet logo]()
$176
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.
Wed 9/1611:15 am -
2 stops27h 20m
Deal found 8/16![Porter Airlines logo]()
$179
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:45 am -
1 stop27h 15m
Deal found 8/19![Multiple Airlines logo]()
$180
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.
Wed 9/2311:15 am -
2 stops27h 20m
Deal found 8/19![Porter Airlines logo]()
$181
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1911:15 am -
2 stops23h 45m
Deal found 8/18![Porter Airlines logo]()
$186
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2211:40 am -
2 stops23h 20m
Deal found 8/18![Porter Airlines logo]()
$191
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:05 pm -
1 stop19h 35m
Deal found 8/19![WestJet logo]()
$197
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 9/272:55 pm -
2 stops30h 44m
Deal found 8/17![Multiple Airlines logo]()
$202
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.
Wed 9/167:00 am -
3 stops17h 23m
Deal found 8/16![Multiple Airlines logo]()
$207
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:20 am -
1 stop6h 58m
Deal found 8/19![Porter Airlines logo]()
$211
Find flight deals from Winnipeg to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Chicago (CHI). 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 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $282 (Kiwi.com) |
One-way from | $152 (FlightHub) |
Popular in | January |
Cheapest in | October |
Average price | $656 |
Good round-trip deal | $566 or less |
Good one-way deal | $389 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Winnipeg to Chicago 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 21, 2026.
Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Thu 9/17
6:15 am-2:35 pm
1 stop8h 20m
Chicago Midway
Sun 9/20
3:20 pm-12:55 am
1 stop9h 35m
$386
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Wed 9/9
9:20 am-4:18 pm
1 stop6h 58m
Chicago O'Hare Intl
Sat 9/12
8:03 am-3:19 pm
1 stop7h 16m
$515
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Wed 9/9
5:44 pm-9:07 am
2 stops15h 23m
Chicago Midway
Sat 9/12
6:05 am-11:30 pm
2 stops17h 25m
$562
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Fri 10/9
9:05 pm-4:58 pm
2 stops19h 53m
Chicago O'Hare Intl
Mon 10/12
12:30 pm-9:40 pm
2 stops9h 10m
$615
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Fri 10/9
6:40 am-5:38 pm
1 stop10h 58m
Chicago O'Hare Intl
Mon 10/12
11:41 am-9:40 pm
2 stops9h 59m
$649
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Tue 10/13
6:00 am-6:00 pm
2 stops12h 00m
Chicago Midway
Sun 10/18
1:27 pm-12:55 am
2 stops11h 28m
$662
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Thu 10/29
5:00 am-6:00 pm
2 stops13h 00m
Chicago Midway
Sun 11/1
5:31 pm-7:53 pm
1 stop26h 22m
$664
WinnipegChicago
YWG Winnipeg - MDW Chicago Midway
YWGMDW
Winnipeg
Wed 9/9
6:40 am-6:19 pm
1 stop11h 39m
Chicago Midway
Sat 9/12
5:37 pm-12:55 am
2 stops31h 18m
$688
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Wed 11/18
2:15 pm-4:50 pm
Nonstop2h 35m
Chicago O'Hare Intl
Sun 11/22
9:35 am-12:23 pm
Nonstop2h 48m
$699
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Thu 10/1
2:00 pm-4:35 pm
Nonstop2h 35m
Chicago O'Hare Intl
Thu 10/8
6:00 am-8:57 pm
1 stop14h 57m
$700
Showing 1-10 of 45 resultsSorted by cheapest first
Compare providers for flights from Winnipeg to Chicago
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 Winnipeg to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars |
- Most accurate provider: When it comes to deals on Winnipeg-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Winnipeg-Chicago 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 Winnipeg-Chicago 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 Winnipeg to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Winnipeg with our price prediction graph.
YWG-CHI
YWG-ORD
YWG-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Winnipeg to Chicago
YWG-CHI
YWG-ORD
YWG-MDW
What is the cheapest month to book a flight from Winnipeg to Chicago?
Currently, September is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $401). Flying from Winnipeg to Chicago in June is currently the most expensive (average of $692). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from YWG to CHI?
Find hourly flight availability from Winnipeg to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 21, 2026.
When flying from Winnipeg to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Winnipeg to Chicago
Explore weekly flight availability from Winnipeg to Chicago. 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 21, 2026.
The most flights from YWG to CHI 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 (7 on average).
How much does it cost to fly round-trip from Winnipeg to Chicago?
Airfare is below average for this route at the moment.
Winnipeg to Chicago flights typically cost between $412 and $708 in October.The cheapest round-trip price found within the last 5 days was $282 on WestJet (Oct 16-Oct 19).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated August 21, 2026.
Read through reviews of airlines operating flights from Winnipeg to Chicago, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Food
6.7
Boarding
7.7
Crew
8.1
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Comfort
7.3
Food
6.7
Boarding
7.7
Crew
8.1
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Winnipeg to Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Winnipeg and Chicago flights
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Other flights from Winnipeg
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Top airline flying from Winnipeg to Chicago
Discover the top airline that operate flights from Winnipeg to Chicago. 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 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$335 | Average$667 | FlexibilityNo cancel fee | On-time69% |