$166+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Oct 25 — Nov 11
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 25, 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 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:30 pm -
1 stop7h 25m
Mon 10/269:35 pm -
2 stops14h 05m
Deal found 9/21![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:30 pm -
1 stop7h 25m
Thu 10/297:00 am -
1 stop10h 40m
Deal found 9/21![Multiple Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/126:20 pm -
1 stop14h 55m
Mon 11/166:55 pm -
1 stop16h 45m
Deal found 9/23![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:30 pm -
1 stop7h 25m
Tue 10/279:35 pm -
2 stops15h 16m
Deal found 9/21![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 stop7h 25m
Sat 10/316:00 am -
2 stops12h 16m
Deal found 9/23![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 stop7h 25m
Fri 10/309:35 pm -
2 stops15h 16m
Deal found 9/23![Multiple Airlines logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 stop7h 25m
Sun 11/18:35 pm -
2 stops22h 10m
Deal found 9/23![Multiple Airlines logo]()
$388
This Mytrip deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/410:15 am -
1 stop14h 29m
Wed 11/115:00 am -
1 stop14h 58m
Deal found 9/20![Multiple Airlines logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:30 pm -
2 stops16h 05m
Tue 10/275:00 am -
1 stop12h 40m
Deal found 9/21![Multiple Airlines logo]()
$395
This Mytrip deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:45 am -
1 stop13h 10m
Wed 10/289:35 pm -
2 stops20h 12m
Deal found 9/21![Multiple Airlines logo]()
$434
This Mytrip deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2011:45 am -
1 stop8h 05m
Tue 10/279:35 pm -
2 stops20h 12m
Deal found 9/21![Multiple Airlines logo]()
$441
This Mytrip deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:45 am -
1 stop13h 10m
Thu 10/299:35 pm -
2 stops20h 12m
Deal found 9/21![Multiple Airlines logo]()
$443
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 25, 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 25, 2026.
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:50 pm -
1 stop7h 07m
Mon 11/27:00 am -
1 stop7h 37m
Deal found 9/22![American Airlines logo]()
$537
This Porter Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 50m
Sat 11/287:00 am -
1 stop7h 46m
Deal found 9/21![Porter Airlines logo]()
$666
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 12/38:04 am -
2 stops8h 30m
Tue 12/86:25 am -
2 stops9h 52m
Deal found 9/22![Delta logo]()
$767
This oojo deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/151:00 pm -
2 stops11h 44m
Sun 1/178:05 pm -
2 stops16h 28m
Deal found 9/21![WestJet logo]()
$824
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:35 am -
Nonstop2h 48m
Wed 11/112:15 pm -
Nonstop2h 35m
Deal found 9/20![United Airlines logo]()
$868
This Mytrip deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:20 pm -
3 stops22h 45m
Mon 10/128:00 am -
2 stops27h 00m
Deal found 9/19![Multiple Airlines logo]()
$996
This Porter Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:06 am -
1 stop7h 14m
Fri 10/307:00 am -
1 stop7h 20m
Deal found 9/20![Porter Airlines logo]()
$666
This Porter Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 11/122:50 pm -
1 stop7h 07m
Mon 11/167:00 am -
1 stop7h 37m
Deal found 9/24![Porter Airlines logo]()
$683
This FlightHub deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:30 pm -
1 stop18h 50m
Mon 10/129:20 am -
1 stop10h 10m
Deal found 9/24![Porter Airlines logo]()
$692
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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.
Sun 1/241:00 pm -
2 stops10h 34m
Mon 2/16:35 am -
1 stop5h 16m
Deal found 9/22![Delta logo]()
$873
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/289:29 am -
Nonstop2h 54m
Mon 11/22:15 pm -
Nonstop2h 35m
Deal found 9/21![United Airlines logo]()
$886
This Porter Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 11/88:45 pm -
1 stop14h 00m
Sun 11/157:00 am -
1 stop7h 37m
Deal found 9/24![Porter Airlines logo]()
$707
This WestJet deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:27 pm -
2 stops22h 53m
Wed 11/118:35 pm -
2 stops13h 49m
Deal found 9/20![WestJet logo]()
$956
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:35 am -
Nonstop2h 48m
Mon 12/72:15 pm -
Nonstop2h 45m
Deal found 9/21![United Airlines logo]()
$886
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 12/310:24 am -
1 stop6h 10m
Sun 12/612:54 pm -
2 stops10h 00m
Deal found 9/22![Delta logo]()
$889
This Expedia deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:24 am -
1 stop6h 10m
Tue 12/86:25 am -
1 stop10h 25m
Deal found 9/22![WestJet logo]()
$1,001
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2410:34 am -
1 stop6h 08m
Sat 11/2812:45 pm -
1 stop3h 54m
Deal found 9/20![Delta logo]()
$911
This Porter Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:29 pm -
1 stop23h 21m
Tue 10/277:00 am -
1 stop7h 20m
Deal found 9/20![Porter Airlines logo]()
$775
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:29 am -
2 stops7h 46m
Wed 10/285:00 am -
2 stops17h 33m
Deal found 9/20![Delta logo]()
$965
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 11/45:31 pm -
1 stop5h 48m
Wed 11/116:35 am -
2 stops6h 16m
Deal found 9/24![Delta logo]()
$1,061
Last-minute flights from Chicago to ManitobaDiscover last-minute flight deals from Chicago to Manitoba. Data last updated September 25, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Manitoba. Data last updated September 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:30 pm -
1 stop7h 25m
Fri 10/309:35 pm -
2 stops15h 16m
Deal found 9/20![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:30 pm -
1 stop7h 25m
Tue 10/276:00 am -
2 stops12h 45m
Deal found 9/20![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:30 pm -
1 stop7h 25m
Sat 10/242:55 pm -
2 stops14h 45m
Deal found 9/20![Multiple Airlines logo]()
$435
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:30 pm -
1 stop7h 25m
Mon 10/264:00 pm -
1 stop13h 16m
Deal found 9/20![Multiple Airlines logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:30 pm -
1 stop7h 25m
Wed 10/288:05 pm -
2 stops14h 24m
Deal found 9/20![WestJet logo]()
$552
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:30 pm -
1 stop7h 25m
Tue 10/275:40 pm -
1 stop3h 47m
Deal found 9/20![WestJet logo]()
$558
This Mytrip deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2011:45 am -
1 stop8h 05m
Tue 10/279:35 pm -
2 stops20h 12m
Deal found 9/21![Multiple Airlines logo]()
$441
This Mytrip deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:45 am -
1 stop13h 10m
Wed 10/289:35 pm -
2 stops20h 12m
Deal found 9/21![Multiple Airlines logo]()
$434
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/213:20 pm -
1 stop9h 35m
Tue 10/279:35 pm -
2 stops20h 12m
Deal found 9/24![Multiple Airlines logo]()
$482
This Mytrip deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:45 am -
1 stop13h 10m
Thu 10/299:35 pm -
2 stops20h 12m
Deal found 9/21![Multiple Airlines logo]()
$443
This Mytrip deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/296:16 am -
2 stops18h 54m
Sun 11/18:35 pm -
2 stops21h 12m
Deal found 9/24![Multiple Airlines logo]()
$459
This Mytrip deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/306:42 pm -
2 stops22h 43m
Mon 11/28:35 pm -
2 stops21h 12m
Deal found 9/23![Multiple Airlines logo]()
$485
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 25, 2026.
Search for one-way flight options from Chicago to Manitoba. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:20 pm -
2 stops23h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Porter Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:30 pm -
1 stop7h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![WestJet logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:20 pm -
1 stop25h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/612:20 pm -
2 stops28h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:20 pm -
1 stop16h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/233:20 pm -
1 stop17h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:20 pm -
2 stops23h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:30 pm -
1 stop17h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![WestJet logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/306:42 pm -
2 stops22h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:50 pm -
2 stops21h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:20 pm -
2 stops23h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Porter Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:15 am -
2 stops16h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$203
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 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $361 (Kiwi.com) |
One-way from | $166 (Kiwi.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 25, 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
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Fri 10/23
3:20 pm-8:40 am
1 stop17h 20m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$175
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Sat 10/24
3:20 pm-2:20 pm
2 stops23h 00m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$178
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 10/30
7:50 pm-1:10 am
2 stops29h 20m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 10/28
7:28 pm-1:10 am
2 stops29h 42m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$199
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 11/6
6:20 pm-6:10 pm
2 stops23h 50m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$202
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Tue 10/27
9:53 am-5:25 pm
2 stops31h 32m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$208
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Wed 11/11
6:16 am-12:10 am
2 stops17h 54m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$209
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Sat 11/7
6:42 pm-4:25 pm
2 stops21h 43m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Fri 11/6
6:42 pm-12:10 am
2 stops29h 28m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$217
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 10/14
8:30 am-12:55 am
3 stops40h 25m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$222
Showing 1-10 of 38 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.
MDW-YWG
ORD-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
MDW-YWG
ORD-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 $479). 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 25, 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.
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 25, 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.
Overall
7.4
Boarding
7.7
Food
6.7
Comfort
7.3
Entertainment
7.1
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.4
Boarding
7.7
Food
6.7
Comfort
7.3
Entertainment
7.1
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.4
Boarding
7.7
Food
6.7
Comfort
7.3
Entertainment
7.1
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 September 25, 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 25, 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% |