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$499+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — YWG
May 29 — Jun 51
Fri 5/29
Fri 6/5
1 adult, Economy
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Cheap flight deals from Oakland to Winnipeg

Cheapest flights from Oakland to Winnipeg
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 April 29, 2026.

This Orbitz deal was found by Cheapflights users on 4/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2610:35 am
OAK
-
YWG
2 stops12h 20m
Multiple Airlines
Mon 6/12:55 pm
YWG
-
OAK
2 stops11h 04m
Multiple Airlines
Deal found 4/28$972
This Delta deal was found by Cheapflights users on 4/27. 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.
Tue 4/2812:34 pm
OAK
-
YWG
2 stops8h 56m
Delta
Thu 4/3011:55 am
YWG
-
OAK
2 stops13h 59m
Delta
Deal found 4/27$1,680
This Delta deal was found by Cheapflights users on 4/28. 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 4/2912:34 pm
OAK
-
YWG
2 stops8h 56m
Delta
Fri 5/111:55 am
YWG
-
OAK
2 stops13h 59m
Delta
Deal found 4/28$1,691

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 April 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$972
(Orbitz)

One-way from

$499
(Expedia)

Popular in

December

Cheapest in

September

Average price

$391
Provider with most accurate pricing for Oakland-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oakland-Winnipeg flights.
Search Deals
From Oakland to Winnipeg
Search Deals
One-way flight from Oakland to Winnipeg
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

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 April 29, 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

Price

Cheapest round-trip
Quickest round-trip

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Tue 5/26

11:30 pm-11:10 am

3 stops33h 40m

Winnipeg

Mon 6/1

9:05 pm-9:44 pm

3 stops26h 39m

$1,282
Cheapest one-way

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Tue 5/26

10:35 am-12:55 am

2 stops12h 20m

$499
Quickest one-way

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Thu 5/28

6:00 am-5:25 pm

2 stops9h 25m

$750

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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.
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.

  • Can I find deals for flights from Oakland to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Oakland to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Winnipeg.

  • Can I find deals for business class flights from Oakland to Winnipeg?

    Yes. Cheapflights offers flight deals from Oakland to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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