$227+ Cheap flights from Oakland, CA (OAK) to Winnipeg (YWG)
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.
OAK — YWG
Sep 12 — Sep 191
Round-trip
1 adult, Economy
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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 Oakland to Winnipeg
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Cheapest flights from Oakland to WinnipegExplore the most affordable flight options available from Oakland to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2026.
Explore the most affordable flight options available from Oakland to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:17 am -
2 stops12h 38m
Mon 9/215:00 pm -
1 stop20h 51m
Deal found 8/10![Multiple Airlines logo]()
$417
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 9/276:51 pm -
1 stop27h 44m
Sun 10/49:05 pm -
2 stops40h 46m
Deal found 8/12![Multiple Airlines logo]()
$473
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 9/812:13 pm -
2 stops31h 57m
Mon 9/145:00 pm -
1 stop20h 51m
Deal found 8/9![Multiple Airlines logo]()
$487
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2712:39 pm -
2 stops8h 51m
Sun 10/43:58 pm -
2 stops10h 01m
Deal found 8/12![Delta logo]()
$1,017
This Booking.com deal was found by Cheapflights users on 8/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:07 am -
2 stops9h 33m
Tue 9/86:00 am -
2 stops14h 55m
Deal found 8/12![Multiple Airlines logo]()
$1,119
Best flights from Oakland to WinnipegDiscover carefully curated flight deals from Oakland to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
Discover carefully curated flight deals from Oakland to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:17 am -
1 stop12h 18m
Mon 9/215:00 pm -
1 stop20h 51m
Deal found 8/10![Multiple Airlines logo]()
$446
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 9/812:13 pm -
2 stops31h 57m
Mon 9/145:00 pm -
1 stop20h 51m
Deal found 8/9![Multiple Airlines logo]()
$487
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2712:39 pm -
2 stops8h 51m
Sun 10/43:58 pm -
2 stops10h 01m
Deal found 8/12![Delta logo]()
$1,017
This Booking.com deal was found by Cheapflights users on 8/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:07 am -
2 stops9h 33m
Tue 9/86:00 am -
2 stops14h 55m
Deal found 8/12![Multiple Airlines logo]()
$1,119
This Delta deal was found by Cheapflights users on 8/8. 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.
Thu 9/36:00 am -
2 stops8h 52m
Wed 9/163:58 pm -
2 stops10h 01m
Deal found 8/8![Delta logo]()
$1,553
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:00 am -
2 stops8h 52m
Fri 9/43:58 pm -
2 stops9h 58m
Deal found 8/9![Delta logo]()
$1,620
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1812:37 pm -
2 stops8h 52m
Sun 12/206:35 am -
2 stops11h 57m
Deal found 8/11![Delta logo]()
$1,792
Last-minute flights from Oakland to WinnipegDiscover last-minute flight deals from Oakland to Winnipeg. Data last updated August 13, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Winnipeg. Data last updated August 13, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 8/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:07 am -
2 stops9h 33m
Tue 9/86:00 am -
2 stops14h 55m
Deal found 8/12![Multiple Airlines logo]()
$1,119
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 9/812:13 pm -
2 stops31h 57m
Mon 9/145:00 pm -
1 stop20h 51m
Deal found 8/9![Multiple Airlines logo]()
$487
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:17 am -
2 stops12h 38m
Mon 9/215:00 pm -
1 stop20h 51m
Deal found 8/10![Multiple Airlines logo]()
$417
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 9/276:51 pm -
1 stop27h 44m
Sun 10/49:05 pm -
2 stops40h 46m
Deal found 8/12![Multiple Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2712:39 pm -
2 stops8h 51m
Sun 10/43:58 pm -
2 stops10h 01m
Deal found 8/12![Delta logo]()
$1,017
One-way flights from Oakland to WinnipegSearch for one-way flight options from Oakland to Winnipeg. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
Search for one-way flight options from Oakland to Winnipeg. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
This Trip.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:51 pm -
2 stops20h 34m
Deal found 8/9![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:51 pm -
2 stops28h 04m
Deal found 8/10![Multiple Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:00 am -
2 stops8h 52m
Deal found 8/9![Delta logo]()
$861
Find flight deals from Oakland to Winnipeg
Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $417 (Kiwi.com) |
One-way from | $227 (Trip.com) |
Popular in | December |
Cheapest in | September |
Average price | $439 |
Cheapflights Fare Finder
Customize your flight search to find flights from Oakland to Winnipeg 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 2,558,603 searches. Data last updated August 13, 2026.
Use the filters below to find and compare flights from Oakland to Winnipeg that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OaklandWinnipeg
OAK Oakland - YWG Winnipeg
OAKYWG
Oakland
Thu 9/17
10:17 am-12:35 am
1 stop12h 18m
Winnipeg
Mon 9/21
5:00 pm-11:51 am
1 stop20h 51m
$446
OaklandWinnipeg
OAK Oakland - YWG Winnipeg
OAKYWG
Oakland
Tue 9/8
12:13 pm-10:10 pm
2 stops31h 57m
Winnipeg
Mon 9/14
5:00 pm-11:51 am
1 stop20h 51m
$487
OaklandWinnipeg
OAK Oakland - YWG Winnipeg
OAKYWG
Oakland
Sun 9/27
12:39 pm-11:30 pm
2 stops8h 51m
Winnipeg
Sun 10/4
3:58 pm-11:59 pm
2 stops10h 01m
$1,017
OaklandWinnipeg
OAK Oakland - YWG Winnipeg
OAKYWG
Oakland
Thu 9/3
10:07 am-9:40 pm
2 stops9h 33m
Winnipeg
Tue 9/8
6:00 am-6:55 pm
2 stops14h 55m
$1,119
OaklandWinnipeg
OAK Oakland - YWG Winnipeg
OAKYWG
Oakland
Thu 9/3
6:00 am-4:52 pm
2 stops8h 52m
Winnipeg
Wed 9/16
3:58 pm-11:59 pm
2 stops10h 01m
$1,553
Quickest round-trip
OaklandWinnipeg
OAK Oakland - YWG Winnipeg
OAKYWG
Oakland
Sun 8/30
6:00 am-4:52 pm
2 stops8h 52m
Winnipeg
Fri 9/4
3:58 pm-11:56 pm
2 stops9h 58m
$1,620
OaklandWinnipeg
OAK Oakland - YWG Winnipeg
OAKYWG
Oakland
Fri 12/18
12:37 pm-11:29 pm
2 stops8h 52m
Winnipeg
Sun 12/20
6:35 am-4:32 pm
2 stops11h 57m
$1,792
Cheapest one-way
OaklandWinnipeg
OAK Oakland - YWG Winnipeg
OAKYWG
Oakland
Fri 9/18
6:51 pm-5:25 pm
2 stops20h 34m
$227
OaklandWinnipeg
OAK Oakland - YWG Winnipeg
OAKYWG
Oakland
Thu 9/10
6:51 pm-12:55 am
2 stops28h 04m
$232
Quickest one-way
OaklandWinnipeg
OAK Oakland - YWG Winnipeg
OAKYWG
Oakland
Sun 8/30
6:00 am-4:52 pm
2 stops8h 52m
$861
Sorted by cheapest first
- Most accurate provider: When it comes to deals on Oakland, California-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Oakland, California-Winnipeg flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Oakland, California-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Oakland, California-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Oakland to Winnipeg
Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Oakland with our price prediction graph.
OAK-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.
Related info for your journey
Find useful and relevant information for your journey from Oakland to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Winnipeg?
Book flights to Winnipeg if you plan to visit one of these locationsPortage la Prairie
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