$184+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Nov 12 — Nov 191
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 October 13, 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 October 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 12/148:15 am -
2 stops16h 55m
Wed 12/167:00 am -
1 stop11h 37m
Deal found 10/8![Multiple Airlines logo]()
$400
This Mytrip deal was found by Cheapflights users on 10/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:28 pm -
2 stops21h 57m
Thu 10/299:35 pm -
2 stops21h 10m
Deal found 10/9![Multiple Airlines logo]()
$453
This Mytrip deal was found by Cheapflights users on 10/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:42 pm -
2 stops22h 43m
Thu 10/299:35 pm -
2 stops20h 12m
Deal found 10/9![Multiple Airlines logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:49 am -
2 stops17h 21m
Sun 11/297:55 pm -
1 stop21h 45m
Deal found 10/11![Multiple Airlines logo]()
$471
This Mytrip deal was found by Cheapflights users on 10/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:50 pm -
2 stops21h 35m
Tue 11/39:35 pm -
2 stops20h 55m
Deal found 10/9![Multiple Airlines logo]()
$473
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Sun 12/208:10 am -
1 stop30h 30m
Sun 1/109:35 pm -
2 stops25h 48m
Deal found 10/9![Multiple Airlines logo]()
$477
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Sun 12/208:10 am -
1 stop30h 30m
Mon 1/117:00 am -
1 stop16h 23m
Deal found 10/9![Multiple Airlines logo]()
$479
This Mytrip deal was found by Cheapflights users on 10/11. 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.
Tue 11/107:35 pm -
2 stops27h 20m
Tue 11/179:35 pm -
2 stops20h 55m
Deal found 10/11![Multiple Airlines logo]()
$487
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Tue 12/1512:15 pm -
1 stop9h 42m
Wed 12/167:00 am -
1 stop11h 37m
Deal found 10/8![Multiple Airlines logo]()
$503
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Sun 12/209:23 pm -
1 stop17h 17m
Mon 1/119:35 pm -
2 stops26h 11m
Deal found 10/9![Multiple Airlines logo]()
$511
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Sun 12/209:23 pm -
1 stop17h 17m
Sat 1/99:35 pm -
2 stops26h 11m
Deal found 10/9![Multiple Airlines logo]()
$515
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Sun 12/208:10 am -
1 stop30h 30m
Sat 1/99:35 pm -
2 stops14h 15m
Deal found 10/9![Multiple Airlines logo]()
$518
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 October 13, 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 October 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:49 am -
2 stops17h 21m
Sun 11/297:55 pm -
1 stop21h 45m
Deal found 10/11![Multiple Airlines logo]()
$471
This Porter Airlines deal was found by Cheapflights users on 10/10. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/32:50 pm -
1 stop7h 02m
Mon 11/97:00 am -
1 stop7h 37m
Deal found 10/10![Porter Airlines logo]()
$699
This Air Canada deal was found by Cheapflights users on 10/8. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/44:30 pm -
1 stop8h 14m
Wed 11/112:15 pm -
Nonstop2h 35m
Deal found 10/8![Air Canada logo]()
$785
This Delta deal was found by Cheapflights users on 10/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/149:37 am -
2 stops7h 57m
Wed 12/167:00 am -
1 stop9h 16m
Deal found 10/8![Delta logo]()
$867
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Sun 12/209:23 pm -
1 stop17h 17m
Mon 1/119:35 pm -
2 stops26h 11m
Deal found 10/9![Multiple Airlines logo]()
$511
This Mytrip deal was found by Cheapflights users on 10/11. 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.
Tue 11/107:35 pm -
2 stops29h 35m
Tue 11/179:35 pm -
3 stops19h 32m
Deal found 10/11![Multiple Airlines logo]()
$540
This Porter Airlines deal was found by Cheapflights users on 10/10. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:20 pm -
2 stops23h 46m
Tue 12/17:00 am -
1 stop7h 36m
Deal found 10/10![Porter Airlines logo]()
$717
This Air Canada deal was found by Cheapflights users on 10/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/264:30 pm -
1 stop8h 14m
Sun 11/293:15 pm -
Nonstop1h 35m
Deal found 10/11![Air Canada logo]()
$827
This Porter Airlines deal was found by Cheapflights users on 10/12. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/22:52 pm -
1 stop7h 05m
Tue 4/67:00 am -
1 stop7h 20m
Deal found 10/12![Porter Airlines logo]()
$764
This Delta deal was found by Cheapflights users on 10/11. 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.
Wed 11/2510:34 am -
1 stop7h 08m
Wed 12/212:54 pm -
1 stop3h 56m
Deal found 10/11![Delta logo]()
$909
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2512:30 pm -
1 stop5h 12m
Wed 12/29:35 pm -
2 stops17h 20m
Deal found 10/11![Multiple Airlines logo]()
$791
This Porter Airlines deal was found by Cheapflights users on 10/10. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:42 am -
1 stop12h 10m
Sun 11/87:00 am -
1 stop7h 37m
Deal found 10/10![Porter Airlines logo]()
$796
This Delta deal was found by Cheapflights users on 10/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/41:27 pm -
2 stops10h 52m
Wed 11/116:35 am -
1 stop5h 15m
Deal found 10/8![Delta logo]()
$934
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 4/26:00 am -
1 stop8h 40m
Tue 4/68:35 am -
2 stops15h 24m
Deal found 10/12![Multiple Airlines logo]()
$807
This Delta deal was found by Cheapflights users on 10/11. 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.
Thu 11/510:12 am -
1 stop7h 38m
Thu 11/121:45 pm -
1 stop2h 54m
Deal found 10/11![Delta logo]()
$946
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 10/223:20 pm -
1 stop25h 05m
Tue 10/279:35 pm -
2 stops20h 12m
Deal found 10/12![Multiple Airlines logo]()
$833
Last-minute flights from Chicago to ManitobaDiscover last-minute flight deals from Chicago to Manitoba. Data last updated October 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Manitoba. Data last updated October 13, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Fri 10/2311:45 am -
1 stop20h 55m
Tue 10/279:35 pm -
2 stops26h 12m
Deal found 10/8![Multiple Airlines logo]()
$674
This Mytrip deal was found by Cheapflights users on 10/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:28 pm -
2 stops21h 57m
Thu 10/299:35 pm -
2 stops21h 10m
Deal found 10/9![Multiple Airlines logo]()
$453
This Mytrip deal was found by Cheapflights users on 10/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:42 pm -
2 stops22h 43m
Thu 10/299:35 pm -
2 stops20h 12m
Deal found 10/9![Multiple Airlines logo]()
$466
This Mytrip deal was found by Cheapflights users on 10/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:50 pm -
2 stops21h 35m
Tue 11/39:35 pm -
2 stops20h 55m
Deal found 10/9![Multiple Airlines logo]()
$473
This Mytrip deal was found by Cheapflights users on 10/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:42 pm -
2 stops22h 43m
Tue 11/39:35 pm -
2 stops20h 12m
Deal found 10/9![Multiple Airlines logo]()
$528
This Mytrip deal was found by Cheapflights users on 10/11. 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.
Thu 11/57:50 pm -
2 stops29h 20m
Thu 11/1210:00 am -
2 stops8h 35m
Deal found 10/11![Multiple Airlines logo]()
$567
This Mytrip deal was found by Cheapflights users on 10/11. 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.
Tue 11/107:35 pm -
2 stops27h 20m
Tue 11/179:35 pm -
2 stops20h 55m
Deal found 10/11![Multiple Airlines logo]()
$487
This Mytrip deal was found by Cheapflights users on 10/10. 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.
Tue 11/249:09 am -
2 stops32h 16m
Tue 12/19:35 pm -
2 stops13h 58m
Deal found 10/10![Multiple Airlines logo]()
$611
This Mytrip deal was found by Cheapflights users on 10/11. 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.
Wed 11/259:07 am -
2 stops16h 03m
Wed 12/29:35 pm -
2 stops17h 20m
Deal found 10/11![Multiple Airlines logo]()
$606
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:49 am -
2 stops17h 21m
Sun 11/297:55 pm -
1 stop21h 45m
Deal found 10/11![Multiple Airlines logo]()
$471
This Booking.com deal was found by Cheapflights users on 10/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/269:09 am -
2 stops26h 11m
Sun 11/299:35 pm -
2 stops14h 46m
Deal found 10/11![Multiple Airlines logo]()
$654
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 -
1 stop9h 37m
Fri 1/17:00 am -
1 stop13h 16m
Deal found 10/8![Multiple Airlines logo]()
$553
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 October 13, 2026.
Search for one-way flight options from Chicago to Manitoba. Find affordable one-way fares based on user searches. Data last updated October 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 11/177:35 pm -
2 stops21h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$184
This Trip.com deal was found by Cheapflights users on 10/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:16 am -
2 stops17h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/186:00 am -
1 stop8h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 11/187:35 pm -
2 stops21h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$205
This Mytrip deal was found by Cheapflights users on 10/12. 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 11/267:49 am -
2 stops17h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$211
This Mytrip deal was found by Cheapflights users on 10/12. 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 11/269:09 am -
2 stops16h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 11/176:08 am -
2 stops35h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 11/186:42 pm -
2 stops30h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Sun 11/86:20 pm -
1 stop15h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Mon 11/97:50 pm -
2 stops21h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$226
This Trip.com deal was found by Cheapflights users on 10/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:08 am -
2 stops17h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 11/197:31 am -
2 stops17h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$236
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 October 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $354 (Kiwi.com) |
One-way from | $184 (Kiwi.com) |
Popular in | August |
Cheapest in | February |
Average price | $479 |
Good round-trip deal | $817 or less |
Good one-way deal | $394 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 October 13, 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 1/18
6:00 am-2:40 pm
1 stop8h 40m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$194
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Thu 11/26
9:09 am-1:10 am
2 stops16h 01m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$211
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 11/26
7:49 am-1:10 am
2 stops17h 21m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$211
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Thu 11/19
6:08 am-1:10 am
2 stops19h 02m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$213
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Wed 11/18
6:42 pm-1:10 am
2 stops30h 28m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$213
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 11/9
7:50 pm-5:25 pm
2 stops21h 35m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$226
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Sun 11/8
6:08 am-11:55 pm
2 stops17h 47m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$228
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Tue 11/17
12:27 pm-5:25 pm
3 stops28h 58m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$244
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Sun 11/8
6:00 am-11:55 pm
3 stops17h 55m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$253
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Sun 11/1
12:15 pm-10:15 am
1 stop22h 00m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$276
Showing 1-10 of 34 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 October 13, 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 October 13, 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).
How much does it cost to fly round-trip from Chicago to Manitoba?
Airfare is below average for this route at the moment.
Chicago to Manitoba flights typically cost between $446 and $817 in January.The cheapest round-trip price found within the last 5 days was $354 on Multiple Airlines (Jan 13-Jan 15).
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 October 13, 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.
Entertainment
7.1
Comfort
7.3
Food
6.7
Overall
7.4
Boarding
7.7
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Entertainment
7.1
Comfort
7.3
Food
6.7
Overall
7.4
Boarding
7.7
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Entertainment
7.1
Comfort
7.3
Food
6.7
Overall
7.4
Boarding
7.7
Crew
8.1
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 October 13, 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 October 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$222 | Average$675 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$322 | Average$780 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$362 | Average$762 | FlexibilityNo cancel fee | On-time69% |