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Oakland

$133+ Cheap flights from Maryland to Oakland, CA (OAK)

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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — OAK
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap flight deals from Maryland to Oakland

Cheapest flights from Maryland to Oakland
Explore the most affordable flight options available from Maryland to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 15, 2025.

This Delta deal was found by Cheapflights users on 12/14. 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 12/226:45 pmPHL - OAK
1 stop8h 13mDelta
Thu 12/2512:34 pmOAK - PHL
1 stop7h 44mDelta
Deal found 12/14$436
This Southwest deal was found by Cheapflights users on 12/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:35 amPHL - OAK
1 stop11h 05mSouthwest
Wed 12/319:00 amOAK - PHL
1 stop10h 50mSouthwest
Deal found 12/14$470
This Southwest deal was found by Cheapflights users on 12/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:35 amPHL - OAK
1 stop11h 05mSouthwest
Thu 1/15:40 amOAK - PHL
2 stops8h 35mSouthwest
Deal found 12/14$510
This Southwest deal was found by Cheapflights users on 12/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:15 pmPHL - OAK
1 stop8h 25mSouthwest
Fri 1/25:00 amOAK - PHL
1 stop9h 00mSouthwest
Deal found 12/14$537
This Delta deal was found by Cheapflights users on 12/14. 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 12/257:05 amPHL - OAK
1 stop7h 49mDelta
Wed 12/3112:34 pmOAK - PHL
1 stop7h 44mDelta
Deal found 12/14$579
This Delta deal was found by Cheapflights users on 12/13. 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 12/1912:22 pmPHL - OAK
2 stops14h 46mDelta
Mon 12/225:53 amOAK - PHL
1 stop8h 44mDelta
Deal found 12/13$584
This Southwest deal was found by Cheapflights users on 12/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amDCA - OAK
1 stop11h 05mSouthwest
Sat 1/36:20 amOAK - DCA
1 stop10h 35mSouthwest
Deal found 12/14$602
This Southwest deal was found by Cheapflights users on 12/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:45 pmIAD - OAK
1 stop7h 35mSouthwest
Sat 1/38:25 pmOAK - IAD
1 stop13h 40mSouthwest
Deal found 12/14$630
This Southwest deal was found by Cheapflights users on 12/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3012:45 pmDCA - OAK
2 stops12h 10mSouthwest
Fri 1/26:05 amOAK - DCA
1 stop12h 50mSouthwest
Deal found 12/14$636
This Delta deal was found by Cheapflights users on 12/13. 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 12/317:05 amIAD - OAK
1 stop18h 42mDelta
Thu 1/812:38 pmOAK - IAD
1 stop8h 10mDelta
Deal found 12/13$647
This Southwest deal was found by Cheapflights users on 12/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:10 amDCA - OAK
2 stops14h 35mSouthwest
Tue 12/306:05 amOAK - DCA
1 stop12h 50mSouthwest
Deal found 12/12$655
This Southwest deal was found by Cheapflights users on 12/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1710:40 amBWI - OAK
1 stop10h 30mSouthwest
Sat 1/105:30 amOAK - BWI
1 stop6h 35mSouthwest
Deal found 12/14$670

Find flight deals from Maryland to Oakland

Keep the following information in mind while searching for Maryland to Oakland flight deals. Data was last updated December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$268
(Southwest)

One-way from

$133
(Trip.com)

Popular in

December

Cheapest in

February

Average price

$496

Good round-trip deal

$742 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-San Francisco flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-San Francisco flights.
Search Deals
From Maryland to Oakland
Search Deals
One-way flight from Maryland to Oakland
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Maryland to Oakland.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maryland to Oakland 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 December 15, 2025.
Use the filters below to find and compare flights from Maryland to Oakland that are best for you.

Fly from

Maryland

Fly to

Oakland

Route

Depart

Return

Price

Washington, D.C.Oakland

DCA - OAK

DCAOAK

Washington, D.C. Reagan-National

Wed 1/14

9:30 am-2:05 pm

1 stop7h 35m

Oakland

Wed 1/21

8:10 am-6:00 pm

1 stop6h 50m

$268

Washington, D.C.Oakland

IAD - OAK

IADOAK

Washington, D.C. Dulles Intl

Wed 1/14

7:05 am-11:57 am

1 stop7h 52m

Oakland

Sat 1/24

12:33 pm-11:48 pm

1 stop8h 15m

$297

Washington, D.C.Oakland

IAD - OAK

IADOAK

Washington, D.C. Dulles Intl

Wed 1/14

7:05 am-11:57 am

1 stop7h 52m

Oakland

Wed 1/21

12:33 pm-11:48 pm

1 stop8h 15m

$297

Washington, D.C.Oakland

DCA - OAK

DCAOAK

Washington, D.C. Reagan-National

Tue 1/13

5:10 pm-10:53 pm

1 stop8h 43m

Oakland

Wed 1/14

5:55 am-6:27 pm

2 stops9h 32m

$302

Washington, D.C.Oakland

DCA - OAK

DCAOAK

Washington, D.C. Reagan-National

Wed 1/7

5:10 pm-10:53 pm

1 stop8h 43m

Oakland

Wed 1/14

5:55 am-6:27 pm

2 stops9h 32m

$302

Washington, D.C.Oakland

IAD - OAK

IADOAK

Washington, D.C. Dulles Intl

Tue 1/13

9:00 am-4:14 pm

2 stops10h 14m

Oakland

Wed 1/21

12:33 pm-11:48 pm

1 stop8h 15m

$302

Washington, D.C.Oakland

IAD - OAK

IADOAK

Washington, D.C. Dulles Intl

Tue 1/13

7:05 am-11:57 am

1 stop7h 52m

Oakland

Tue 1/20

4:54 pm-9:13 am

2 stops13h 19m

$302

Washington, D.C.Oakland

DCA - OAK

DCAOAK

Washington, D.C. Reagan-National

Fri 1/9

5:10 pm-10:53 pm

1 stop8h 43m

Oakland

Wed 1/14

5:55 am-4:00 pm

1 stop7h 05m

$307

Washington, D.C.Oakland

DCA - OAK

DCAOAK

Washington, D.C. Reagan-National

Tue 1/13

12:55 pm-10:53 pm

2 stops12h 58m

Oakland

Tue 1/20

4:54 pm-9:10 am

2 stops13h 16m

$307

Washington, D.C.Oakland

IAD - OAK

IADOAK

Washington, D.C. Dulles Intl

Tue 1/27

7:00 am-4:14 pm

2 stops12h 14m

Oakland

Tue 2/3

5:00 pm-9:13 am

2 stops13h 13m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 60 results
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Best time to book a flight from Maryland to Oakland

Have a flexible travel schedule? Discover the best time to fly to Oakland from Maryland 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 Maryland to Oakland

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

Currently, March is the cheapest month in which you can book a flight from Maryland to Oakland, California (average of $102). Flying from Maryland to Oakland, California in September is currently the most expensive (average of $289). 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.

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

Find hourly flight availability from Maryland to Oakland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 15, 2025.

It’s typically best to fly out from Maryland to Oakland, California at noon. Doing so could potentially save you 80% on the flight price compared to flying in the morning, which is usually more expensive.

Related info for your journey

Find useful and relevant information for your journey from Maryland to Oakland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Oakland from Maryland?

    If you book a flight to Oakland from Maryland, you will be flying to Oakland, which is the city’s only airport. Oakland (OAK) is located 7.0 mi from the center of Oakland.

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

    For as low as $268, Southwest can have you in Oakland, California from Maryland in 7h 35m. The distance from Maryland to Oakland, California is about 2425 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Maryland to Oakland, California?

    The most popular flight routes from Maryland to Oakland, California are Washington, D.C. Dulles Intl - Oakland, Baltimore/Washington - Oakland and Philadelphia - Oakland.

  • What are the cheapest flights from Maryland to Oakland, California?

    On average you can expect to pay $742 for a flight from Maryland to Oakland, California. The cheapest flight overall is $742 while the most popular route, (Washington, D.C. Dulles Intl - Oakland) is currently priced at $297.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Maryland to Oakland 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 Maryland to Oakland, California?

    Currently, March is the cheapest month in which you can book a flight from Maryland to Oakland, California (average of $102). Flying from Maryland to Oakland, California in September is currently the most expensive (average of $289). 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

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Alternative routes for Maryland to Oakland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Maryland to Oakland

Discover the top 2 airlines that operate flights from Maryland to Oakland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$104Average$243FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$376Average$492FlexibilityNo cancel feeOn-time63%

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