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$134+ Cheap flights from Oakland, CA (OAK) to Maryland

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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BWI
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap flight deals from Oakland to Maryland

Cheapest flights from Oakland to Maryland
Explore the most affordable flight options available from Oakland to Maryland. 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.
Thu 12/2512:34 pmOAK - PHL
1 stop7h 44mDelta
Wed 1/77:00 amPHL - OAK
1 stop7h 57mDelta
Deal found 12/14$331
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.
Wed 12/2412:34 pmOAK - PHL
1 stop7h 44mDelta
Thu 1/87:00 amPHL - OAK
1 stop7h 57mDelta
Deal found 12/14$354
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 12/225:53 amOAK - PHL
1 stop8h 44mDelta
Thu 1/87:00 amPHL - OAK
1 stop7h 57mDelta
Deal found 12/14$414
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:40 amOAK - DCA
2 stops9h 15mSouthwest
Wed 1/76:05 amDCA - OAK
1 stop11h 00mSouthwest
Deal found 12/13$442
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:35 amOAK - IAD
1 stop7h 55mSouthwest
Wed 1/74:30 pmIAD - OAK
1 stop8h 15mSouthwest
Deal found 12/13$451
This Southwest deal was found by Cheapflights users on 12/15. 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 12/315:25 amOAK - IAD
1 stop8h 40mSouthwest
Mon 1/57:50 pmIAD - OAK
1 stop7h 20mSouthwest
Deal found 12/15$457
This Southwest deal was found by Cheapflights users on 12/15. 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 12/318:20 amOAK - DCA
1 stop7h 00mSouthwest
Mon 1/56:10 amDCA - OAK
1 stop12h 10mSouthwest
Deal found 12/15$458
This Southwest deal was found by Cheapflights users on 12/15. 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.
Mon 12/295:55 amOAK - IAD
2 stops10h 15mSouthwest
Mon 1/57:50 pmIAD - OAK
1 stop7h 20mSouthwest
Deal found 12/15$462
This Southwest deal was found by Cheapflights users on 12/15. 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 12/306:05 amOAK - DCA
1 stop12h 50mSouthwest
Mon 1/56:00 amDCA - OAK
1 stop7h 25mSouthwest
Deal found 12/15$462
This Southwest deal was found by Cheapflights users on 12/15. 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 12/306:35 amOAK - IAD
1 stop7h 55mSouthwest
Mon 1/57:50 pmIAD - OAK
1 stop7h 20mSouthwest
Deal found 12/15$471
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 12/255:53 amOAK - IAD
2 stops31h 55mDelta
Wed 1/77:05 amIAD - OAK
1 stop7h 52mDelta
Deal found 12/14$474
This Southwest deal was found by Cheapflights users on 12/15. 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.
Mon 12/296:05 amOAK - DCA
1 stop12h 50mSouthwest
Mon 1/56:00 amDCA - OAK
1 stop7h 25mSouthwest
Deal found 12/15$476

Find flight deals from Oakland to Maryland

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$277
(Southwest)

One-way from

$134
(Southwest)

Popular in

December

Cheapest in

February

Average price

$542
Provider with most accurate pricing for San Francisco-Washington, D.C. (WAS) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-Washington, D.C. (WAS) flights.
Search Deals
From Oakland to Maryland
Search Deals
One-way flight from Oakland to Maryland
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Maryland 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 Oakland to Maryland that are best for you.

Fly from

Oakland

Fly to

Maryland

Route

Depart

Return

Price

OaklandWashington, D.C.

OAK - DCA

OAKDCA

Oakland

Wed 2/11

8:10 am-9:59 pm

1 stop10h 49m

Washington, D.C. Reagan-National

Sat 2/14

5:06 pm-9:24 am

1 stop19h 18m

$297

OaklandWashington, D.C.

OAK - DCA

OAKDCA

Oakland

Wed 1/7

5:55 am-10:00 pm

2 stops13h 05m

Washington, D.C. Reagan-National

Tue 1/13

5:10 pm-10:53 pm

1 stop8h 43m

$302

OaklandWashington, D.C.

OAK - IAD

OAKIAD

Oakland

Thu 1/8

5:55 am-11:10 pm

2 stops14h 15m

Washington, D.C. Dulles Intl

Wed 1/14

7:05 am-11:57 am

1 stop7h 52m

$306

OaklandPhiladelphia

OAK - PHL

OAKPHL

Oakland

Sat 5/16

5:05 pm-5:43 am

1 stop9h 38m

Philadelphia

Tue 5/19

6:40 pm-11:49 pm

1 stop8h 09m

$309

OaklandPhiladelphia

OAK - PHL

OAKPHL

Oakland

Fri 1/30

5:55 am-5:25 pm

1 stop8h 30m

Philadelphia

Mon 2/2

5:17 pm-11:53 pm

2 stops9h 36m

$314

OaklandWashington, D.C.

OAK - DCA

OAKDCA

Oakland

Thu 1/8

5:55 am-6:27 pm

2 stops9h 32m

Washington, D.C. Reagan-National

Wed 1/14

9:54 am-4:14 pm

2 stops9h 20m

$317

OaklandWashington, D.C.

OAK - DCA

OAKDCA

Oakland

Wed 1/21

5:55 am-10:00 pm

2 stops13h 05m

Washington, D.C. Reagan-National

Thu 1/22

2:32 pm-11:53 pm

2 stops12h 21m

$317

OaklandWashington, D.C.

OAK - IAD

OAKIAD

Oakland

Wed 1/7

5:55 am-11:10 pm

2 stops14h 15m

Washington, D.C. Dulles Intl

Tue 1/13

12:29 pm-10:53 pm

2 stops13h 24m

$321

OaklandWashington, D.C.

OAK - IAD

OAKIAD

Oakland

Wed 3/4

6:15 am-5:20 pm

1 stop8h 05m

Washington, D.C. Dulles Intl

Sun 3/8

7:05 am-11:58 pm

1 stop19h 53m

$330

OaklandWashington, D.C.

OAK - IAD

OAKIAD

Oakland

Mon 1/26

8:10 am-5:04 pm

2 stops29h 54m

Washington, D.C. Dulles Intl

Thu 1/29

6:04 pm-11:03 am

1 stop19h 59m

$335

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 Oakland to Maryland

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

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

Currently, February is the cheapest month in which you can book a flight from Oakland, California to Maryland (average of $143). Flying from Oakland, California to Maryland in November is currently the most expensive (average of $343). 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 OAK to MD?

Find hourly flight availability from Oakland to Maryland. 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.

Unlike at noon, when flights are generally more expensive, you can save up to 62% on flights from Oakland, California to Maryland by exploring options for tickets in the evening.

Reviews of airlines servicing Maryland

Get insights into the airlines that provide service to Maryland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Maryland. Reviews last updated December 15, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Oakland to Maryland to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,249 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
7.9
Good
4,249 reviews
Southwest
7.9
Good
4,249 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Delta
7.9
Good
8,008 reviews
Southwest
7.9
Good
4,249 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,092 reviews
Southwest
7.9
Good
4,249 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Maryland. 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 from for flights from Oakland to Maryland?

    Oakland (OAK), located 7.0 mi from the city center, is the airport you fly out of when you book flights from Oakland to Maryland.

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

    For as low as $277, Southwest can have you in Maryland from Oakland, California in 9h 20m. Airlines will cover a distance of 2425 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The most popular route from Oakland, California to Maryland is Oakland - Washington, D.C. Dulles Intl. You may also consider Oakland - Baltimore/Washington or Oakland - Washington, D.C. Reagan-National.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Oakland, California to Maryland (average of $143). Flying from Oakland, California to Maryland in November is currently the most expensive (average of $343). 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 Oakland to Maryland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Oakland to Maryland

Discover the top 3 airlines that operate flights from Oakland to Maryland. 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
DeltaCheapest$267Average$486FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$353Average$480FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$377Average$531FlexibilityNo cancel feeOn-time69%

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