HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Winnipeg

$383+ Cheap flights from Oakland, CA (OAK) to Winnipeg (YWG)

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 7/27. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — YWG
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oakland to Winnipeg 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 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 June 12, 2025.

Round-trip from

$490
(Mytrip)

Popular in

November

Cheapest in

February

Average price

$426
From Oakland to Winnipeg
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

Find 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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/266:00 amOAK - YWG
3 stops35h 24mMultiple Airlines
Sat 8/28:30 amYWG - OAK
3 stops17h 03mMultiple Airlines
Deal found 6/10$490

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 June 12, 2025.
Use the filters below to find and compare flights from Oakland to Winnipeg that are best for you.

Fly from

Oakland

Fly to

Winnipeg

Route

Depart

Return

Price

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Sun 7/27

2:38 pm-12:31 am

2 stops31h 53m

Winnipeg

Sun 8/3

3:15 pm-8:28 am

2 stops19h 13m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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, August is the cheapest month in which you can book a flight from Oakland, California to Winnipeg (average of $358). Flying from Oakland, California to Winnipeg in December is currently the most expensive (average of $497). 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.

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

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.

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

    Currently, August is the cheapest month in which you can book a flight from Oakland, California to Winnipeg (average of $358). Flying from Oakland, California to Winnipeg in December is currently the most expensive (average of $497). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.