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$638+ 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 5/21. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — YWG
Apr 24 — May 11
Fri 4/24
Fri 5/1
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 March 25, 2026.

This Delta deal was found by Cheapflights users on 3/22. 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.
Sat 4/185:55 am
OAK
-
YWG
2 stops15h 35m
Delta
Tue 4/215:20 pm
YWG
-
OAK
2 stops25h 04m
Delta
Deal found 3/22$660
This Delta deal was found by Cheapflights users on 3/22. 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.
Fri 4/175:04 pm
OAK
-
YWG
2 stops28h 26m
Delta
Tue 4/215:20 pm
YWG
-
OAK
2 stops25h 04m
Delta
Deal found 3/22$766
This Delta deal was found by Cheapflights users on 3/22. 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.
Sat 4/185:55 am
OAK
-
YWG
2 stops15h 35m
Delta
Mon 4/2011:55 am
YWG
-
OAK
2 stops30h 29m
Delta
Deal found 3/22$809
This Delta deal was found by Cheapflights users on 3/24. 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 4/155:55 am
OAK
-
YWG
2 stops15h 35m
Delta
Thu 4/235:20 pm
YWG
-
OAK
2 stops8h 34m
Delta
Deal found 3/24$823
This Delta deal was found by Cheapflights users on 3/22. 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 4/165:55 am
OAK
-
YWG
2 stops15h 35m
Delta
Tue 4/215:20 pm
YWG
-
OAK
2 stops20h 33m
Delta
Deal found 3/22$832
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:55 am
OAK
-
YWG
2 stops15h 32m
Delta
Fri 8/218:50 am
YWG
-
OAK
2 stops9h 41m
Delta
Deal found 3/23$866
This Delta deal was found by Cheapflights users on 3/22. 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.
Fri 4/175:04 pm
OAK
-
YWG
2 stops28h 26m
Delta
Mon 4/2011:55 am
YWG
-
OAK
2 stops25h 58m
Delta
Deal found 3/22$915
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/56:00 am
OAK
-
YWG
2 stops15h 29m
Delta
Sat 7/116:40 am
YWG
-
OAK
2 stops11h 42m
Delta
Deal found 3/23$931
This Delta deal was found by Cheapflights users on 3/24. 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.
Sun 4/55:55 am
OAK
-
YWG
2 stops15h 40m
Delta
Sat 4/1811:55 am
YWG
-
OAK
2 stops11h 46m
Delta
Deal found 3/24$960
This Expedia deal was found by Cheapflights users on 3/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1410:20 am
OAK
-
YWG
2 stops9h 20m
Multiple Airlines
Wed 7/2212:50 pm
YWG
-
OAK
2 stops12h 09m
Multiple Airlines
Deal found 3/23$962
This Delta deal was found by Cheapflights users on 3/22. 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 4/165:55 am
OAK
-
YWG
2 stops15h 35m
Delta
Mon 4/2011:55 am
YWG
-
OAK
2 stops25h 58m
Delta
Deal found 3/22$981
This FlightHub deal was found by Cheapflights users on 3/23. 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.
Sun 7/57:52 am
OAK
-
YWG
2 stops12h 18m
Multiple Airlines
Sat 7/116:00 am
YWG
-
OAK
2 stops18h 59m
Multiple Airlines
Deal found 3/23$1,067

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 March 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$660
(Delta)

One-way from

$638
(Delta)

Popular in

December

Cheapest in

September

Average price

$475
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. 19% potential increase in price ($102 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 25, 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

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Sat 4/18

5:55 am-11:30 pm

2 stops15h 35m

Winnipeg

Tue 4/21

5:20 pm-4:24 pm

2 stops25h 04m

$660

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Fri 4/17

5:04 pm-11:30 pm

2 stops28h 26m

Winnipeg

Tue 4/21

5:20 pm-4:24 pm

2 stops25h 04m

$766

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Wed 4/15

5:55 am-11:30 pm

2 stops15h 35m

Winnipeg

Thu 4/23

5:20 pm-11:54 pm

2 stops8h 34m

$823

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Mon 8/10

5:55 am-11:27 pm

2 stops15h 32m

Winnipeg

Fri 8/21

8:50 am-4:31 pm

2 stops9h 41m

$866

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Fri 4/17

5:04 pm-11:30 pm

2 stops28h 26m

Winnipeg

Mon 4/20

11:55 am-11:53 am

2 stops25h 58m

$915

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Sun 7/5

6:00 am-11:29 pm

2 stops15h 29m

Winnipeg

Sat 7/11

6:40 am-4:22 pm

2 stops11h 42m

$931

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Sun 4/5

5:55 am-11:35 pm

2 stops15h 40m

Winnipeg

Sat 4/18

11:55 am-9:41 pm

2 stops11h 46m

$960
Quickest round-trip

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Tue 7/14

10:20 am-9:40 pm

2 stops9h 20m

Winnipeg

Wed 7/22

12:50 pm-10:59 pm

2 stops12h 09m

$962

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Sun 7/5

7:52 am-10:10 pm

2 stops12h 18m

Winnipeg

Sat 7/11

6:00 am-10:59 pm

2 stops18h 59m

$1,067

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Thu 4/16

5:55 am-11:30 pm

2 stops15h 35m

Winnipeg

Mon 4/20

5:20 pm-11:54 pm

2 stops8h 34m

$1,079

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 13 resultsSorted by cheapest first
1
2
  • 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.

Cheapflights Insights

Everything you need to know about your flight from Oakland to Winnipeg

What is the cheapest month to book a flight from Oakland, California to Winnipeg?

Currently, June is the cheapest month in which you can book a flight from Oakland, California to Winnipeg (average of $114). Flying from Oakland, California to Winnipeg in December is currently the most expensive (average of $386). 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.

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.

  • How long is the flight from Oakland, California to Winnipeg?

    Departing from Oakland, California to Winnipeg will take you 15h 35m. The distance from Oakland, California to Winnipeg is about 1492 mi.

  • 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.

  • What is the cheapest month to book a flight from Oakland, California to Winnipeg?

    Currently, June is the cheapest month in which you can book a flight from Oakland, California to Winnipeg (average of $114). Flying from Oakland, California to Winnipeg in December is currently the most expensive (average of $386). 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.

See more FAQs

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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