$177+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Dec 9 — Dec 161
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 November 9, 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 November 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/98:30 am -
2 stops15h 40m
Sat 12/1211:00 am -
1 stop25h 34m
Deal found 11/6![Multiple Airlines logo]()
$424
This Mytrip deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1010:29 pm -
2 stops17h 56m
Fri 12/119:35 pm -
2 stops17h 55m
Deal found 11/5![Multiple Airlines logo]()
$442
This Mytrip deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/105:02 pm -
2 stops23h 23m
Fri 12/119:35 pm -
2 stops14h 58m
Deal found 11/6![Multiple Airlines logo]()
$443
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1110:29 pm -
2 stops17h 56m
Sun 12/137:55 pm -
1 stop16h 39m
Deal found 11/6![Multiple Airlines logo]()
$454
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:21 am -
1 stop16h 24m
Sat 12/124:45 pm -
2 stops13h 16m
Deal found 11/5![Multiple Airlines logo]()
$495
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/106:21 am -
1 stop16h 24m
Sun 12/136:30 am -
1 stop28h 54m
Deal found 11/4![Multiple Airlines logo]()
$501
This Kiwi.com deal was found by Cheapflights users on 11/9. 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.
Wed 12/231:11 pm -
2 stops34h 59m
Wed 12/307:00 am -
1 stop18h 01m
Deal found 11/9![Multiple Airlines logo]()
$712
This oojo deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/510:24 am -
1 stop13h 15m
Sat 12/129:35 pm -
2 stops13h 53m
Deal found 11/7![WestJet logo]()
$740
This oojo deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:30 pm -
1 stop17h 01m
Sun 12/139:35 pm -
2 stops19h 41m
Deal found 11/5![WestJet logo]()
$746
This FlightHub deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/95:30 pm -
1 stop17h 01m
Sat 12/129:35 pm -
2 stops19h 41m
Deal found 11/6![WestJet logo]()
$759
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/206:43 am -
1 stop30h 57m
Mon 12/288:05 pm -
2 stops24h 25m
Deal found 11/7![Multiple Airlines logo]()
$763
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 November 9, 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 November 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 1/195:34 pm -
1 stop20h 06m
Wed 2/37:00 am -
1 stop17h 46m
Deal found 11/4![Multiple Airlines logo]()
$410
This Porter Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 1/142:48 pm -
1 stop7h 11m
Tue 1/196:54 am -
1 stop8h 47m
Deal found 11/4![Porter Airlines logo]()
$718
This oojo deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1010:24 am -
2 stops9h 26m
Fri 12/115:45 pm -
1 stop24h 05m
Deal found 11/6![WestJet logo]()
$771
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 1/116:00 am -
2 stops13h 50m
Wed 1/137:00 am -
1 stop10h 55m
Deal found 11/4![Delta logo]()
$784
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1112:29 pm -
1 stop8h 26m
Sun 12/133:15 pm -
Nonstop2h 45m
Deal found 11/6![United Airlines logo]()
$866
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 1/206:00 am -
1 stop7h 40m
Sun 1/313:15 pm -
1 stop25h 59m
Deal found 11/4![Multiple Airlines logo]()
$521
This Mytrip deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:21 am -
3 stops15h 34m
Sun 12/133:10 pm -
2 stops20h 14m
Deal found 11/6![Multiple Airlines logo]()
$606
This Porter Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 2/52:48 pm -
1 stop7h 11m
Wed 2/106:54 am -
1 stop7h 16m
Deal found 11/4![Porter Airlines logo]()
$718
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 1/2012:44 pm -
1 stop10h 55m
Sun 1/319:35 pm -
2 stops27h 11m
Deal found 11/4![Multiple Airlines logo]()
$623
This oojo deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/109:37 am -
2 stops25h 28m
Sat 12/129:35 pm -
2 stops13h 53m
Deal found 11/5![WestJet logo]()
$788
This Porter Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 1/162:48 pm -
1 stop7h 11m
Tue 1/196:54 am -
1 stop8h 47m
Deal found 11/4![Porter Airlines logo]()
$718
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 1/115:30 am -
2 stops14h 20m
Wed 1/136:00 am -
2 stops15h 07m
Deal found 11/4![Delta logo]()
$798
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 1/146:00 am -
2 stops13h 50m
Sat 1/166:00 am -
2 stops17h 17m
Deal found 11/4![Delta logo]()
$798
This Porter Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 1/78:00 am -
1 stop26h 49m
Sun 1/106:54 am -
1 stop7h 16m
Deal found 11/4![Porter Airlines logo]()
$742
This Justfly.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 1/2010:51 am -
2 stops29h 34m
Sun 1/319:35 pm -
2 stops20h 19m
Deal found 11/4![WestJet logo]()
$833
This Porter Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 2/28:45 pm -
1 stop14h 04m
Thu 2/116:54 am -
1 stop7h 08m
Deal found 11/4![Porter Airlines logo]()
$750
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/206:43 am -
1 stop30h 57m
Mon 12/288:05 pm -
2 stops24h 25m
Deal found 11/7![Multiple Airlines logo]()
$763
This Justfly.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:41 pm -
2 stops16h 24m
Sun 12/136:25 am -
1 stop11h 25m
Deal found 11/6![WestJet logo]()
$842
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/89:55 am -
1 stop5h 05m
Wed 5/1212:30 pm -
1 stop4h 20m
Deal found 11/7![Delta logo]()
$912
This Mytrip deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/185:58 am -
1 stop7h 42m
Tue 12/221:10 pm -
3 stops17h 39m
Deal found 11/8![Multiple Airlines logo]()
$769
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/812:30 pm -
1 stop4h 30m
Fri 5/146:35 am -
1 stop5h 16m
Deal found 11/7![Delta logo]()
$912
Last-minute flights from Chicago to ManitobaDiscover last-minute flight deals from Chicago to Manitoba. Data last updated November 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Manitoba. Data last updated November 9, 2026 and is based on user searches.
This oojo deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/510:24 am -
1 stop13h 15m
Sat 12/129:35 pm -
2 stops13h 53m
Deal found 11/7![WestJet logo]()
$740
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/98:30 am -
2 stops15h 40m
Sat 12/1211:00 am -
1 stop25h 34m
Deal found 11/6![Multiple Airlines logo]()
$424
This FlightHub deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/95:30 pm -
1 stop17h 01m
Sat 12/129:35 pm -
2 stops19h 41m
Deal found 11/6![WestJet logo]()
$759
This Mytrip deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1010:29 pm -
2 stops17h 56m
Fri 12/119:35 pm -
2 stops17h 55m
Deal found 11/5![Multiple Airlines logo]()
$442
This Mytrip deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/105:02 pm -
2 stops23h 23m
Fri 12/119:35 pm -
2 stops14h 58m
Deal found 11/6![Multiple Airlines logo]()
$443
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:21 am -
1 stop16h 24m
Sat 12/124:45 pm -
2 stops13h 16m
Deal found 11/5![Multiple Airlines logo]()
$495
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/106:21 am -
1 stop16h 24m
Sun 12/136:30 am -
1 stop28h 54m
Deal found 11/4![Multiple Airlines logo]()
$501
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1110:29 pm -
2 stops17h 56m
Sun 12/137:55 pm -
1 stop16h 39m
Deal found 11/6![Multiple Airlines logo]()
$454
This oojo deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:30 pm -
1 stop17h 01m
Sun 12/139:35 pm -
2 stops19h 41m
Deal found 11/5![WestJet logo]()
$746
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/206:43 am -
1 stop30h 57m
Mon 12/288:05 pm -
2 stops24h 25m
Deal found 11/7![Multiple Airlines logo]()
$763
This Kiwi.com deal was found by Cheapflights users on 11/9. 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.
Wed 12/231:11 pm -
2 stops34h 59m
Wed 12/307:00 am -
1 stop18h 01m
Deal found 11/9![Multiple Airlines logo]()
$712
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 November 9, 2026.
Search for one-way flight options from Chicago to Manitoba. Find affordable one-way fares based on user searches. Data last updated November 9, 2026.
This Trip.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/88:30 am -
2 stops15h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/105:02 pm -
2 stops23h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1010:29 pm -
2 stops17h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/812:28 pm -
2 stops35h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/3012:15 pm -
2 stops29h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Porter Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/3012:15 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/225:59 pm -
1 stop19h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/205:59 pm -
1 stop19h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:43 am -
2 stops33h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:42 pm -
3 stops27h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/229:09 am -
2 stops39h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/208:35 pm -
2 stops17h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Multiple Airlines logo]()
$340
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 November 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $385 (Kiwi.com) |
One-way from | $177 (Trip.com) |
Popular in | August |
Cheapest in | February |
Average price | $450 |
Good round-trip deal | $542 or less |
Good one-way deal | $316 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 November 9, 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
Thu 12/10
10:29 pm-5:25 pm
2 stops17h 56m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$190
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 11/30
12:15 pm-7:14 pm
2 stops29h 59m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$254
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Thu 12/10
5:02 pm-5:25 pm
3 stops23h 23m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$260
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Tue 12/22
5:59 pm-5:25 pm
2 stops22h 26m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$266
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Tue 12/22
6:43 am-5:25 pm
2 stops33h 42m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$277
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 11/30
9:20 pm-1:10 am
3 stops26h 50m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Mon 11/30
8:42 pm-1:10 am
3 stops27h 28m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$280
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Tue 12/8
12:28 pm-5:25 pm
3 stops27h 57m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$334
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Sat 12/19
8:35 pm-5:25 pm
3 stops43h 50m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$344
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Sat 12/19
7:45 am-2:30 pm
2 stops29h 45m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$352
Showing 1-10 of 35 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, September is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $512). 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 November 9, 2026.
It’s optimal to fly from Chicago to Manitoba in the evening. By choosing this option you can save up to 32% on the cost of your flight, compared to a flight in the afternoon.
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 November 9, 2026.
The most flights from CHI to CAMB are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 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 November 9, 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.
Boarding
7.7
Overall
7.3
Comfort
7.3
Crew
8.1
Food
6.7
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Boarding
7.7
Overall
7.3
Comfort
7.3
Crew
8.1
Food
6.7
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Boarding
7.7
Overall
7.3
Comfort
7.3
Crew
8.1
Food
6.7
Entertainment
7.1
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.
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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 November 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Chicago to Manitoba
Discover the top 3 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 November 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$208 | Average$454 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$291 | Average$865 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$322 | Average$780 | FlexibilityNo cancel fee | On-time67% |