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Oakland

$98+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — OAK
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Maryland to Oakland

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

Round-trip from

$257
(Southwest)

One-way from

$98
(Cheapflightsfares)

Popular in

December

Cheapest in

February

Average price

$416

Good round-trip deal

$742 or less
From Maryland to Oakland
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One-way flight from Maryland to Oakland
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Highest demand for flights based on searches. 6% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Maryland to Oakland.
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Find 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 September 15, 2025.

This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/15:00 pmDCA - OAK
1 stop9h 59mAlaska Airlines
Tue 11/46:30 amOAK - DCA
1 stop12h 29mAlaska Airlines
Deal found 9/14$257
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/297:02 pmBWI - OAK
1 stop7h 30mSpirit Airlines
Wed 10/16:30 amOAK - BWI
1 stop8h 27mSpirit Airlines
Deal found 9/13$264
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:50 pmDCA - OAK
1 stop9h 40mSouthwest
Fri 11/285:25 amOAK - DCA
1 stop6h 30mSouthwest
Deal found 9/13$277
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/295:21 pmPHL - OAK
1 stop9h 11mSpirit Airlines
Wed 10/16:30 amOAK - PHL
1 stop11h 21mSpirit Airlines
Deal found 9/14$281
This Southwest deal was found by Cheapflights users on 9/15. 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 10/216:50 amBWI - OAK
1 stop9h 00mSouthwest
Tue 10/216:15 pmOAK - BWI
1 stop7h 55mSouthwest
Deal found 9/15$281
This Southwest deal was found by Cheapflights users on 9/15. 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 10/84:00 pmDCA - OAK
1 stop8h 45mSouthwest
Sun 10/126:25 amOAK - DCA
1 stop13h 20mSouthwest
Deal found 9/15$282
This Southwest deal was found by Cheapflights users on 9/14. 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 10/256:40 amIAD - OAK
1 stop10h 20mSouthwest
Sun 10/268:40 pmOAK - IAD
1 stop13h 20mSouthwest
Deal found 9/14$282
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/295:21 pmPHL - OAK
1 stop9h 11mMultiple Airlines
Wed 10/16:30 amOAK - PHL
2 stops31h 02mMultiple Airlines
Deal found 9/14$286
This Southwest deal was found by Cheapflights users on 9/14. 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 10/257:25 amDCA - OAK
1 stop14h 30mSouthwest
Sun 10/266:10 amOAK - DCA
1 stop13h 40mSouthwest
Deal found 9/14$288
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/287:02 pmBWI - OAK
1 stop31h 30mSpirit Airlines
Tue 9/306:30 amOAK - BWI
1 stop19h 00mSpirit Airlines
Deal found 9/14$295
This Delta deal was found by Cheapflights users on 9/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/187:10 amPHL - OAK
1 stop7h 38mDelta
Wed 12/35:45 amOAK - PHL
1 stop8h 55mDelta
Deal found 9/12$297
This Trip.com deal was found by Cheapflights users on 9/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/298:16 amBWI - OAK
1 stop18h 16mSpirit Airlines
Fri 10/310:56 amOAK - BWI
2 stops14h 34mSpirit Airlines
Deal found 9/14$297

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 September 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

Sat 11/15

6:05 am-10:45 am

1 stop7h 40m

Oakland

Sun 11/16

8:00 am-10:00 pm

1 stop11h 00m

$282

Washington, D.C.Oakland

DCA - OAK

DCAOAK

Washington, D.C. Reagan-National

Sat 11/22

11:35 am-1:30 am

2 stops16h 55m

Oakland

Fri 11/28

5:35 am-7:30 pm

2 stops10h 55m

$293

PhiladelphiaOakland

PHL - OAK

PHLOAK

Philadelphia

Wed 11/19

7:10 am-11:48 am

1 stop7h 38m

Oakland

Wed 12/3

5:45 am-5:40 pm

1 stop8h 55m

$297

Washington, D.C.Oakland

IAD - OAK

IADOAK

Washington, D.C. Dulles Intl

Sat 11/1

5:00 pm-9:25 pm

1 stop7h 25m

Oakland

Tue 11/4

5:25 am-5:05 pm

1 stop8h 40m

$297

BaltimoreOakland

BWI - OAK

BWIOAK

Baltimore/Washington

Tue 10/21

7:15 am-11:50 am

1 stop7h 35m

Oakland

Tue 10/28

4:51 pm-9:13 am

2 stops13h 22m

$302

Washington, D.C.Oakland

DCA - OAK

DCAOAK

Washington, D.C. Reagan-National

Sat 11/1

5:10 pm-9:32 pm

1 stop7h 22m

Oakland

Tue 11/4

5:55 am-7:33 pm

2 stops10h 38m

$302

PhiladelphiaOakland

PHL - OAK

PHLOAK

Philadelphia

Tue 11/18

7:10 am-11:48 am

1 stop7h 38m

Oakland

Sat 12/6

5:45 am-5:40 pm

1 stop8h 55m

$303

PhiladelphiaOakland

PHL - OAK

PHLOAK

Philadelphia

Sat 12/6

7:05 am-11:50 am

1 stop7h 45m

Oakland

Tue 12/9

5:45 am-5:40 pm

1 stop8h 55m

$303

PhiladelphiaOakland

PHL - OAK

PHLOAK

Philadelphia

Tue 10/28

7:05 am-11:50 am

1 stop7h 45m

Oakland

Mon 11/3

5:55 am-5:38 pm

1 stop8h 43m

$303

PhiladelphiaOakland

PHL - OAK

PHLOAK

Philadelphia

Wed 11/19

7:10 am-11:48 am

1 stop7h 38m

Oakland

Thu 12/4

5:45 am-5:40 pm

1 stop8h 55m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

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, April is the cheapest month in which you can book a flight from Maryland to Oakland, California (average of $183). Flying from Maryland to Oakland, California in November is currently the most expensive (average of $259). 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 September 15, 2025.

When flying from Maryland to Oakland, California, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 $318, Southwest can have you in Oakland, California from Maryland in 7h 30m. The distance from Maryland to Oakland, California is about 2439 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Maryland to Oakland, California one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $111. Users have also found prices from $112 and $129 on Spirit Airlines and Hawaiian Airlines, respectively.

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

    The most popular flight routes from Maryland to Oakland, California are Baltimore/Washington - Oakland, Washington, D.C. Dulles Intl - Oakland and Washington, D.C. Reagan-National - 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, (Baltimore/Washington - Oakland) is currently priced at $295.

  • 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, April is the cheapest month in which you can book a flight from Maryland to Oakland, California (average of $183). Flying from Maryland to Oakland, California in November is currently the most expensive (average of $259). 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$104Average$243FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$388Average$487FlexibilityNo cancel feeOn-time63%

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