$145+ Cheap flights from Chicago (CHI) to Manitoba
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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Oct 15 — Oct 221
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Manitoba 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 Chicago to Manitoba
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Cheapest flights from Chicago to ManitobaExplore the most affordable flight options available from Chicago to Manitoba. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2026.
Explore the most affordable flight options available from Chicago to Manitoba. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:30 pm -
1 stop7h 25m
Mon 10/197:00 am -
1 stop9h 40m
Deal found 9/10![WestJet logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/115:30 pm -
1 stop7h 25m
Sun 10/187:00 am -
1 stop9h 40m
Deal found 9/13![WestJet logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:20 pm -
1 stop18h 25m
Mon 10/127:45 am -
1 stop27h 15m
Deal found 9/12![Multiple Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:20 pm -
1 stop18h 25m
Fri 10/26:05 pm -
1 stop16h 55m
Deal found 9/10![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:20 pm -
1 stop18h 25m
Sat 10/34:15 pm -
2 stops18h 45m
Deal found 9/10![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:20 pm -
2 stops19h 23m
Fri 10/27:55 pm -
1 stop15h 05m
Deal found 9/10![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:04 am -
2 stops16h 51m
Mon 10/197:00 am -
1 stop9h 40m
Deal found 9/10![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:20 pm -
1 stop17h 20m
Sat 10/34:25 pm -
1 stop18h 35m
Deal found 9/13![Multiple Airlines logo]()
$366
This Trip.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:30 pm -
1 stop7h 25m
Wed 10/217:10 pm -
1 stop21h 30m
Deal found 9/10![WestJet logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:04 am -
2 stops16h 51m
Sun 10/187:00 am -
1 stop9h 40m
Deal found 9/12![Multiple Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:30 pm -
1 stop7h 25m
Mon 10/269:35 pm -
2 stops15h 16m
Deal found 9/9![Multiple Airlines logo]()
$381
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:20 pm -
2 stops23h 50m
Sun 11/15:00 am -
1 stop12h 40m
Deal found 9/12![Multiple Airlines logo]()
$382
Best flights from Chicago to ManitobaDiscover carefully curated flight deals from Chicago to Manitoba that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2026.
Discover carefully curated flight deals from Chicago to Manitoba that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3011:45 am -
1 stop20h 55m
Fri 10/25:10 pm -
1 stop17h 50m
Deal found 9/13![Multiple Airlines logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:30 pm -
1 stop7h 25m
Sun 9/275:44 pm -
1 stop3h 49m
Deal found 9/9![WestJet logo]()
$537
This Porter Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:03 am -
1 stop7h 16m
Tue 9/299:20 am -
1 stop6h 58m
Deal found 9/13![Porter Airlines logo]()
$635
This Goibibo deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Goibibo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:03 am -
1 stop6h 46m
Wed 11/112:15 pm -
Nonstop2h 35m
Deal found 9/11![Air Canada logo]()
$724
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:05 am -
2 stops9h 49m
Sat 10/36:40 am -
2 stops9h 34m
Deal found 9/10![Delta logo]()
$747
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:30 pm -
1 stop7h 25m
Sun 9/277:00 am -
2 stops22h 38m
Deal found 9/9![Multiple Airlines logo]()
$531
This Mytrip deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:40 pm -
2 stops13h 40m
Mon 9/219:05 pm -
2 stops17h 50m
Deal found 9/11![Multiple Airlines logo]()
$671
This oojo deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:19 am -
2 stops9h 01m
Sat 10/315:00 am -
2 stops14h 20m
Deal found 9/9![WestJet logo]()
$794
This Porter Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:20 pm -
2 stops26h 38m
Tue 9/2911:15 am -
2 stops23h 45m
Deal found 9/9![Porter Airlines logo]()
$831
This oojo deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:30 pm -
2 stops21h 45m
Fri 10/99:05 pm -
2 stops19h 53m
Deal found 9/12![WestJet logo]()
$816
This Air Canada deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:54 pm -
Nonstop2h 39m
Sun 9/278:10 am -
1 stop6h 42m
Deal found 9/9![Air Canada logo]()
$932
This Mytrip deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:30 pm -
3 stops12h 25m
Fri 10/1610:30 pm -
3 stops31h 22m
Deal found 9/12![Multiple Airlines logo]()
$799
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/41:27 pm -
2 stops9h 52m
Wed 11/116:35 am -
1 stop5h 15m
Deal found 9/14![Delta logo]()
$1,019
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1612:30 pm -
1 stop4h 12m
Wed 12/166:25 am -
2 stops9h 52m
Deal found 9/9![Delta logo]()
$1,033
This oojo deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/812:39 pm -
1 stop23h 30m
Fri 12/185:24 pm -
1 stop24h 00m
Deal found 9/12![WestJet logo]()
$942
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:59 am -
1 stop6h 55m
Sat 10/106:40 am -
2 stops11h 20m
Deal found 9/10![Delta logo]()
$1,105
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:59 am -
1 stop6h 55m
Sat 10/106:40 am -
2 stops11h 20m
Deal found 9/11![Delta logo]()
$1,105
Last-minute flights from Chicago to ManitobaDiscover last-minute flight deals from Chicago to Manitoba. Data last updated September 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Manitoba. Data last updated September 15, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:30 pm -
1 stop18h 49m
Wed 9/239:20 am -
1 stop6h 58m
Deal found 9/13![Porter Airlines logo]()
$871
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals ”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:20 am -
2 stops17h 15m
Tue 9/227:00 am -
1 stop9h 40m
Deal found 9/13![Multiple Airlines logo]()
$884
This Justfly.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:30 pm -
1 stop18h 49m
Tue 9/228:45 pm -
1 stop10h 55m
Deal found 9/13![Porter Airlines logo]()
$896
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:55 pm -
2 stops20h 30m
Mon 9/285:00 pm -
1 stop12h 38m
Deal found 9/14![Multiple Airlines logo]()
$650
This FlightHub deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 9/248:03 am -
1 stop7h 16m
Mon 9/288:45 pm -
1 stop16h 00m
Deal found 9/14![Porter Airlines logo]()
$769
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:20 pm -
2 stops19h 23m
Fri 10/27:55 pm -
1 stop15h 05m
Deal found 9/10![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2911:45 am -
1 stop13h 10m
Sat 10/34:25 pm -
1 stop18h 35m
Deal found 9/13![Multiple Airlines logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:20 pm -
1 stop18h 25m
Fri 10/26:05 pm -
1 stop16h 55m
Deal found 9/10![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:20 pm -
1 stop18h 25m
Sat 10/34:15 pm -
2 stops18h 45m
Deal found 9/10![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:20 pm -
1 stop17h 20m
Sat 10/34:25 pm -
1 stop18h 35m
Deal found 9/13![Multiple Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:20 pm -
1 stop17h 20m
Fri 10/27:55 pm -
1 stop15h 05m
Deal found 9/13![Multiple Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:20 pm -
1 stop18h 25m
Mon 10/127:45 am -
1 stop27h 15m
Deal found 9/12![Multiple Airlines logo]()
$345
One-way flights from Chicago to ManitobaSearch for one-way flight options from Chicago to Manitoba. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
Search for one-way flight options from Chicago to Manitoba. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
This Trip.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/183:20 pm -
2 stops26h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Porter Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:30 pm -
1 stop7h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![WestJet logo]()
$157
This Trip.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1911:45 am -
1 stop13h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$160
This Trip.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:30 pm -
1 stop7h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![WestJet logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:20 pm -
2 stops29h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Porter Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:20 pm -
1 stop16h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:20 pm -
1 stop25h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:42 pm -
3 stops31h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:50 pm -
2 stops20h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$181
This Mytrip deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:40 pm -
1 stop12h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:30 pm -
1 stop17h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![WestJet logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:16 am -
2 stops17h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$191
Find flight deals from Chicago to Manitoba
Keep the following information in mind while searching for Chicago to Manitoba flight deals. Data was last updated September 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $327 (Kiwi.com) |
One-way from | $145 (Trip.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 Chicago to Manitoba 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 15, 2026.
Use the filters below to find and compare flights from Chicago to Manitoba 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
Mon 10/19
5:30 pm-12:55 am
1 stop7h 25m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$157
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 11/18
7:28 pm-4:25 pm
2 stops20h 57m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$182
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Thu 11/12
6:16 am-12:10 am
2 stops17h 54m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$193
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 11/12
6:00 am-12:10 am
3 stops18h 10m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$208
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Fri 10/2
3:20 pm-5:58 pm
2 stops26h 38m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$224
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 1/13
6:00 am-2:40 pm
1 stop8h 40m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$227
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Thu 10/1
3:20 pm-5:58 pm
2 stops26h 38m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$229
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 11/12
2:50 pm-9:57 pm
1 stop7h 07m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 10/1
7:45 pm-10:10 pm
2 stops26h 25m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$238
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Sun 10/18
6:00 am-12:15 am
2 stops18h 15m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$249
Showing 1-10 of 37 resultsSorted by cheapest first
Best time to book a flight from Chicago to Manitoba
Have a flexible travel schedule? Discover the best time to fly to Manitoba from Chicago with our price prediction graph.
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 Manitoba
CHI-CAMB
ORD-YWG
MDW-YWG
What is the cheapest month to book a flight from Chicago to Manitoba?
Currently, October is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $493). Flying from Chicago to Manitoba 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 MB?
Find hourly flight availability from Chicago to Manitoba. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2026.
It’s optimal to fly from Chicago to Manitoba in the afternoon. By choosing this option you can save up to 51% on the cost of your flight, compared to a flight at noon.
Weekly flight availability from Chicago to Manitoba
Explore weekly flight availability from Chicago to Manitoba. 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 15, 2026.
The most flights from CHI to CAMB 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).
Reviews of airlines servicing Manitoba
Get insights into the airlines that provide service to Manitoba. 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 Manitoba. Reviews last updated September 15, 2026.
Get a feel of what it's like to fly with United Airlines and Air Canada from Chicago to Manitoba by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Overall
7.4
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Overall
7.4
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Comfort
7.3
Crew
8.1
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 Manitoba. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chicago to Manitoba
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Manitoba by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Manitoba by cabin class
Find flights from Chicago to Manitoba, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Manitoba flights
Browse other Chicago and Manitoba flight options. Last updated on September 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Manitoba
Discover the top 2 airlines that operate flights from Chicago to Manitoba. 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 15, 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% |