What is the cheapest day to fly from Oakland, California to Winnipeg?

Travelers seeking maximum savings on their Oakland, California to Winnipeg flight should consider departing on Friday mornings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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.

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).

How far in advance should I book a flight from Oakland, California to Winnipeg?

Find a great deal and save up to 205% by booking at least 54 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Oakland, California to Winnipeg within the next two weeks, with the cheapest ticket starting at $318.

What is the cheapest month to fly from Oakland, California to Winnipeg?

Our data shows that February tends to be the cheapest month to fly to Winnipeg from Oakland, California. Users have commonly found prices around $373 for the month, but tickets can be as low as $114. Due to multiple factors, prepare for potentially higher prices in November.

What is the cheapest time of day to fly from OAK to YWG?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oakland, California to Winnipeg as you normally would.

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.

$386+ Flights from Oakland, CA to Winnipeg

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

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

Round-trip from	$386 (Mytrip)
Popular in	November
Cheapest in	February
Average price	$339

From Oakland to Winnipeg

Search Deals

Highest demand for flights based on searches. 9% potential increase in price ($40 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in August 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 August 14, 2025.

Wed 9/102:39 pmOAK - YWG

2 stops19h 02mMultiple Airlines

Wed 9/1710:00 amYWG - OAK

3 stops15h 32mMultiple Airlines

Deal found 8/13

$386

Tue 9/26:00 amOAK - YWG

3 stops37h 30mMultiple Airlines

Fri 9/123:15 pmYWG - OAK

3 stops24h 19mMultiple Airlines

Deal found 8/13

$403

Mon 8/1810:44 amOAK - YWG

3 stops31h 26mMultiple Airlines

Thu 8/216:30 amYWG - OAK

3 stops29h 10mMultiple Airlines

Deal found 8/14

$706

Mon 8/1810:44 amOAK - YWG

3 stops31h 26mMultiple Airlines

Fri 8/229:00 amYWG - OAK

2 stops24h 18mMultiple Airlines

Deal found 8/14

$736

Best flights from Oakland to Winnipeg
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 14, 2025.

Wed 9/102:39 pmOAK - YWG

2 stops19h 02mMultiple Airlines

Wed 9/1710:00 amYWG - OAK

3 stops15h 32mMultiple Airlines

Deal found 8/13

$386

Tue 9/26:00 amOAK - YWG

3 stops37h 30mMultiple Airlines

Fri 9/123:15 pmYWG - OAK

3 stops24h 19mMultiple Airlines

Deal found 8/13

$403

Mon 8/1810:44 amOAK - YWG

3 stops31h 26mMultiple Airlines

Thu 8/216:30 amYWG - OAK

3 stops29h 10mMultiple Airlines

Deal found 8/14

$706

Mon 8/1810:44 amOAK - YWG

3 stops31h 26mMultiple Airlines

Fri 8/229:00 amYWG - OAK

2 stops24h 18mMultiple Airlines

Deal found 8/14

$736

Last-minute flights from Oakland to Winnipeg
Discover last-minute flight deals from Oakland to Winnipeg. Data last updated August 14, 2025 and is based on user searches.

Mon 8/1810:44 amOAK - YWG

3 stops31h 26mMultiple Airlines

Thu 8/216:30 amYWG - OAK

3 stops29h 10mMultiple Airlines

Deal found 8/14

$706

Mon 8/1810:44 amOAK - YWG

3 stops31h 26mMultiple Airlines

Fri 8/229:00 amYWG - OAK

2 stops24h 18mMultiple Airlines

Deal found 8/14

$736

Tue 9/26:00 amOAK - YWG

3 stops37h 30mMultiple Airlines

Fri 9/123:15 pmYWG - OAK

3 stops24h 19mMultiple Airlines

Deal found 8/13

$403

Wed 9/102:39 pmOAK - YWG

2 stops19h 02mMultiple Airlines

Wed 9/1710:00 amYWG - OAK

3 stops15h 32mMultiple Airlines

Deal found 8/13

$386

Fly from

Fly to

Route

Depart

Return

Price

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Wed 9/10

2:39 pm-11:41 am

2 stops19h 02m

Winnipeg

Wed 9/17

10:00 am-11:32 pm

3 stops15h 32m

$386

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Tue 9/2

6:00 am-9:30 pm

3 stops37h 30m

Winnipeg

Fri 9/12

3:15 pm-1:34 pm

3 stops24h 19m

$403

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Mon 8/18

10:44 am-8:10 pm

3 stops31h 26m

Winnipeg

Thu 8/21

6:30 am-9:40 am

3 stops29h 10m

$706

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Mon 8/18

10:44 am-8:10 pm

3 stops31h 26m

Winnipeg

Fri 8/22

9:00 am-7:18 am

2 stops24h 18m

$736

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

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 $495). 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

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 $495). 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

Portage la Prairie

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Oakland to Winnipeg

Los Angeles to Winnipeg flights

Ontario to Winnipeg flights

San Francisco to Winnipeg flights

San Diego to Winnipeg flights

Santa Ana to Winnipeg flights

Las Vegas to Winnipeg flights

Sacramento to Winnipeg flights

Burbank to Winnipeg flights

San Jose to Winnipeg flights

Los Angeles to Brandon flights

Santa Rosa to Winnipeg flights

Other flights to Winnipeg

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.

$386+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Oakland to Winnipeg with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Oakland to Winnipeg

Round-trip from

Popular in

Cheapest in

Average price

Find flight deals from Oakland to Winnipeg

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 14, 2025.

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 14, 2025.

Cheapflights Fare Finder

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

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.

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?

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?

How can I find direct flights from Oakland to Winnipeg?

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

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

Traveling to a place near Winnipeg?

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.

Alternative routes for Oakland to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.

100% Free

Book with Flexibility

Travel Smart

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 August 14, 2025.