$150+ Cheap flights from Chicago (CHI) to Manitoba
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Sep 26 — Oct 31
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 August 27, 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 August 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 10/25:30 pm -
1 stop7h 25m
Sun 10/47:00 am -
1 stop9h 40m
Deal found 8/24![WestJet logo]()
$304
This Jettzy deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/115:30 pm -
1 stop7h 25m
Sun 10/187:00 am -
1 stop9h 40m
Deal found 8/27![WestJet logo]()
$307
This Justfly.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Tue 9/295:30 pm -
1 stop7h 25m
Tue 10/67:00 am -
1 stop9h 40m
Deal found 8/25![WestJet logo]()
$312
This Justfly.com deal was found by Cheapflights users on 8/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:30 pm -
1 stop7h 25m
Sat 9/57:00 am -
1 stop9h 40m
Deal found 8/23![WestJet logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/95:30 pm -
1 stop7h 25m
Fri 10/167:00 am -
1 stop9h 40m
Deal found 8/25![WestJet logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:30 pm -
1 stop7h 25m
Thu 10/156:00 am -
1 stop10h 40m
Deal found 8/27![WestJet logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/2411:45 am -
1 stop9h 00m
Mon 9/2811:15 am -
2 stops23h 45m
Deal found 8/23![Multiple Airlines logo]()
$345
This FlightHub deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:30 pm -
1 stop17h 40m
Sun 9/207:00 am -
1 stop9h 40m
Deal found 8/25![WestJet logo]()
$348
This FlightHub deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/25:30 pm -
1 stop7h 25m
Sat 10/107:10 pm -
1 stop21h 30m
Deal found 8/26![WestJet logo]()
$354
This Mytrip deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:45 am -
1 stop8h 04m
Sun 9/278:45 pm -
1 stop14h 15m
Deal found 8/26![Porter Airlines logo]()
$386
This Mytrip deal was found by Cheapflights users on 8/24. 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.
Mon 9/213:20 pm -
2 stops19h 23m
Mon 9/2811:40 am -
2 stops23h 20m
Deal found 8/24![Porter Airlines logo]()
$617
This Mytrip deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/23:20 pm -
3 stops24h 05m
Sun 10/42:55 pm -
3 stops20h 05m
Deal found 8/26![Multiple Airlines logo]()
$633
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 August 27, 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 August 27, 2026.
This Justfly.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Tue 9/295:30 pm -
1 stop7h 25m
Tue 10/67:00 am -
1 stop9h 40m
Deal found 8/25![WestJet logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/2411:45 am -
1 stop9h 00m
Mon 9/2811:15 am -
2 stops23h 45m
Deal found 8/23![Multiple Airlines logo]()
$345
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Mon 9/289:55 am -
1 stop6h 32m
Tue 9/295:00 am -
1 stop7h 00m
Deal found 8/27![Air Canada logo]()
$658
This FlightHub deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/25:30 pm -
1 stop7h 25m
Sat 10/107:10 pm -
1 stop21h 30m
Deal found 8/26![WestJet logo]()
$354
This Porter Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2611:45 am -
2 stops30h 13m
Tue 9/2911:40 am -
2 stops23h 20m
Deal found 8/26![Porter Airlines logo]()
$714
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:27 am -
2 stops12h 02m
Mon 12/712:59 pm -
2 stops9h 56m
Deal found 8/26![Delta logo]()
$740
This FlightHub deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2911:45 am -
2 stops30h 25m
Sun 11/111:40 am -
2 stops29h 50m
Deal found 8/25![Porter Airlines logo]()
$752
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/2612:50 pm -
1 stop8h 24m
Sun 11/292:15 pm -
Nonstop2h 35m
Deal found 8/27![Air Canada logo]()
$758
This WestJet deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Mon 9/285:30 pm -
1 stop7h 25m
Tue 9/296:15 am -
2 stops10h 44m
Deal found 8/27![WestJet logo]()
$698
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/2610:01 am -
1 stop6h 49m
Tue 11/38:00 am -
1 stop3h 47m
Deal found 8/25![Delta logo]()
$826
This Bravofly deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:55 pm -
2 stops11h 00m
Sun 10/46:05 pm -
2 stops18h 54m
Deal found 8/25![WestJet logo]()
$736
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/297:13 pm -
1 stop4h 17m
Tue 10/612:38 pm -
1 stop4h 09m
Deal found 8/25![Delta logo]()
$826
This Air Canada deal was found by Cheapflights users on 8/23. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:35 am -
Nonstop2h 48m
Wed 11/1112:45 pm -
1 stop7h 13m
Deal found 8/23![Air Canada logo]()
$866
This FlightHub deal was found by Cheapflights users on 8/24. 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 12/115:30 pm -
1 stop18h 39m
Sun 12/135:24 pm -
1 stop18h 35m
Deal found 8/24![WestJet logo]()
$737
This Porter Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/98:06 am -
2 stops9h 52m
Fri 10/1611:40 am -
2 stops28h 39m
Deal found 8/25![Porter Airlines logo]()
$903
This Delta deal was found by Cheapflights users on 8/24. 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 11/49:29 am -
2 stops10h 24m
Wed 11/116:35 am -
2 stops6h 16m
Deal found 8/24![Delta logo]()
$832
This Porter Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/211:45 am -
2 stops30h 13m
Sun 10/411:15 am -
2 stops27h 20m
Deal found 8/25![Porter Airlines logo]()
$917
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 11/41:23 pm -
2 stops9h 56m
Wed 11/115:32 pm -
1 stop4h 01m
Deal found 8/25![Delta logo]()
$836
This KAYAK deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/78:48 am -
2 stops16h 07m
Thu 9/1012:00 pm -
1 stop28h 40m
Deal found 8/27![WestJet logo]()
$902
Last-minute flights from Chicago to ManitobaDiscover last-minute flight deals from Chicago to Manitoba. Data last updated August 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Manitoba. Data last updated August 27, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 8/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:30 pm -
1 stop7h 25m
Sat 9/57:00 am -
1 stop9h 40m
Deal found 8/23![WestJet logo]()
$330
This FlightHub deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/45:30 pm -
1 stop7h 25m
Tue 9/89:20 am -
1 stop6h 59m
Deal found 8/27![Multiple Airlines logo]()
$697
This FlightHub deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/46:59 am -
2 stops17h 56m
Tue 9/87:00 am -
1 stop9h 40m
Deal found 8/27![WestJet logo]()
$781
This Mytrip deal was found by Cheapflights users on 8/24. 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.
Sun 9/64:00 pm -
2 stops17h 35m
Thu 9/106:00 am -
3 stops23h 52m
Deal found 8/24![Multiple Airlines logo]()
$768
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:13 pm -
1 stop4h 17m
Sat 9/1911:15 am -
2 stops23h 45m
Deal found 8/26![Multiple Airlines logo]()
$687
This Mytrip deal was found by Cheapflights users on 8/24. 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.
Mon 9/213:20 pm -
2 stops19h 23m
Mon 9/2811:40 am -
2 stops23h 20m
Deal found 8/24![Porter Airlines logo]()
$617
This Mytrip deal was found by Cheapflights users on 8/24. 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.
Mon 9/213:20 pm -
2 stops19h 23m
Mon 9/289:05 pm -
3 stops13h 55m
Deal found 8/24![Multiple Airlines logo]()
$635
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/2411:45 am -
1 stop9h 00m
Mon 9/2811:15 am -
2 stops23h 45m
Deal found 8/23![Multiple Airlines logo]()
$345
This Mytrip deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:20 pm -
2 stops19h 23m
Thu 10/14:20 pm -
2 stops18h 40m
Deal found 8/25![Multiple Airlines logo]()
$748
This Mytrip deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:45 am -
1 stop8h 04m
Sun 9/278:45 pm -
1 stop14h 15m
Deal found 8/26![Porter Airlines logo]()
$386
This Porter Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2611:45 am -
2 stops30h 13m
Tue 9/2911:40 am -
2 stops23h 20m
Deal found 8/26![Porter Airlines logo]()
$714
This Justfly.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Tue 9/2910:48 am -
2 stops9h 32m
Tue 10/66:15 am -
2 stops9h 59m
Deal found 8/25![WestJet logo]()
$761
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 August 27, 2026.
Search for one-way flight options from Chicago to Manitoba. Find affordable one-way fares based on user searches. Data last updated August 27, 2026.
This FlightHub deal was found by Cheapflights users on 8/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:30 pm -
1 stop7h 25m
Deal found 8/23![WestJet logo]()
$150
This Flightnetwork deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/115:30 pm -
1 stop7h 25m
Deal found 8/27![WestJet logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/83:30 pm -
1 stop9h 05m
Deal found 8/26![Multiple Airlines logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Thu 10/85:30 pm -
2 stops15h 50m
Deal found 8/24![WestJet logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 8/23. 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.
Tue 10/65:30 pm -
2 stops26h 30m
Deal found 8/23![WestJet logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/86:40 pm -
2 stops20h 45m
Deal found 8/27![Multiple Airlines logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 8/23. 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.
Tue 10/63:20 pm -
2 stops19h 23m
Deal found 8/23![Porter Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 8/23. 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.
Tue 10/611:45 am -
3 stops21h 35m
Deal found 8/23![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:05 am -
2 stops53h 05m
Deal found 8/25![Multiple Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/810:01 am -
1 stop6h 49m
Deal found 8/26![Delta logo]()
$386
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/116:04 am -
2 stops10h 46m
Deal found 8/27![Delta logo]()
$391
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 August 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $304 (Kiwi.com) |
One-way from | $150 (FlightHub) |
Popular in | August |
Cheapest in | February |
Average price | $1,256 |
Good round-trip deal | $907 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 August 27, 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
Tue 9/29
5:30 pm-12:55 am
1 stop7h 25m
Winnipeg
Tue 10/6
7:00 am-4:40 pm
1 stop9h 40m
$312
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Thu 9/24
11:45 am-8:45 pm
1 stop9h 00m
Winnipeg
Mon 9/28
11:15 am-11:00 am
2 stops23h 45m
$345
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 10/2
5:30 pm-12:55 am
1 stop7h 25m
Winnipeg
Sat 10/10
7:10 pm-4:40 pm
1 stop21h 30m
$354
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 9/28
9:55 am-4:27 pm
1 stop6h 32m
Winnipeg
Tue 9/29
5:00 am-12:00 pm
1 stop7h 00m
$658
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 9/28
5:30 pm-12:55 am
1 stop7h 25m
Winnipeg
Tue 9/29
6:15 am-4:59 pm
2 stops10h 44m
$698
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Sat 9/26
11:45 am-5:58 pm
2 stops30h 13m
Winnipeg
Tue 9/29
11:40 am-11:00 am
2 stops23h 20m
$714
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 10/2
1:55 pm-12:55 am
2 stops11h 00m
Winnipeg
Sun 10/4
6:05 pm-12:59 pm
2 stops18h 54m
$736
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Fri 12/11
5:30 pm-12:09 pm
1 stop18h 39m
Winnipeg
Sun 12/13
5:24 pm-11:59 am
1 stop18h 35m
$737
ChicagoWinnipeg
MDW Chicago Midway - YWG Winnipeg
MDWYWG
Chicago Midway
Mon 11/23
11:27 am-11:29 pm
2 stops12h 02m
Winnipeg
Mon 12/7
12:59 pm-10:55 pm
2 stops9h 56m
$740
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 10/29
11:45 am-6:10 pm
2 stops30h 25m
Winnipeg
Sun 11/1
11:40 am-5:30 pm
2 stops29h 50m
$752
Showing 1-10 of 29 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 $415). 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 August 27, 2026.
It’s optimal to fly from Chicago to Manitoba at noon. By choosing this option you can save up to 43% on the cost of your flight, compared to a flight in the morning.
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 August 27, 2026.
The most flights from CHI to CAMB are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).
Reviews of airlines servicing Manitoba
Get insights into the airlines that provide service to Manitoba. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Manitoba. Reviews last updated August 27, 2026.
Get a feel of what it's like to fly with United Airlines from Chicago to Manitoba by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.7
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Crew
8.1
Overall
7.4
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Crew
8.1
Overall
7.4
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Manitoba. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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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 August 27, 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 August 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$208 | Average$405 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$362 | Average$762 | FlexibilityNo cancel fee | On-time69% |