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$144+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BWI
Jul 15 — Jul 221
Wed 7/15
Wed 7/22
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 June 15, 2026.

This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 9/2911:55 am
OAK
-
DCA
1 stop7h 25m
Southwest
Tue 10/612:55 pm
DCA
-
OAK
1 stop8h 15m
Southwest
Deal found 6/12$284
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:10 pm
OAK
-
IAD
1 stop19h 35m
Alaska Airlines
Wed 8/197:35 pm
IAD
-
OAK
1 stop18h 31m
Alaska Airlines
Deal found 6/10$297
This Delta deal was found by Cheapflights users on 6/11. 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 9/16:00 am
OAK
-
DCA
1 stop7h 44m
Delta
Wed 9/93:05 pm
DCA
-
OAK
2 stops11h 44m
Delta
Deal found 6/11$302
This Expedia deal was found by Cheapflights users on 6/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/292:15 pm
OAK
-
BWI
1 stop13h 15m
Alaska Airlines
Tue 10/66:12 pm
BWI
-
OAK
1 stop20h 14m
Alaska Airlines
Deal found 6/12$305
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3011:55 pm
OAK
-
PHL
1 stop8h 15m
Southwest
Wed 9/26:25 pm
PHL
-
OAK
1 stop7h 40m
Southwest
Deal found 6/10$305
This Southwest deal was found by Cheapflights users on 6/11. 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 8/295:40 pm
OAK
-
BWI
1 stop9h 50m
Southwest
Sat 9/510:05 am
BWI
-
OAK
1 stop7h 50m
Southwest
Deal found 6/11$309
This Delta deal was found by Cheapflights users on 6/11. 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 9/15:00 pm
OAK
-
BWI
1 stop10h 20m
Delta
Wed 9/92:10 pm
BWI
-
OAK
2 stops12h 39m
Delta
Deal found 6/11$310
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:55 pm
OAK
-
PHL
1 stop8h 40m
Southwest
Wed 8/123:00 pm
PHL
-
OAK
1 stop11h 05m
Southwest
Deal found 6/10$311
This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 9/296:55 pm
OAK
-
BWI
1 stop8h 40m
Southwest
Tue 10/67:10 am
BWI
-
OAK
2 stops9h 05m
Southwest
Deal found 6/12$312
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:00 pm
OAK
-
PHL
1 stop10h 05m
Delta
Mon 8/247:00 pm
PHL
-
OAK
1 stop7h 56m
Delta
Deal found 6/10$321
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:48 am
OAK
-
IAD
1 stop8h 26m
Alaska Airlines
Thu 9/107:47 pm
IAD
-
OAK
1 stop18h 19m
Alaska Airlines
Deal found 6/10$322
This Delta deal was found by Cheapflights users on 6/11. 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 9/16:00 am
OAK
-
DCA
1 stop7h 44m
Delta
Sat 9/55:54 pm
DCA
-
OAK
1 stop7h 44m
Delta
Deal found 6/11$322

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 June 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$284
(Southwest)

One-way from

$144
(Southwest)

Popular in

June

Cheapest in

January

Average price

$557
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. 13% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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 June 15, 2026.
Use the filters below to find and compare flights from Oakland to Maryland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OaklandWashington, D.C.

OAK - DCA

OAKDCA

Oakland

Wed 9/9

8:55 am-8:55 pm

2 stops9h 00m

Washington, D.C. Reagan-National

Sun 9/13

1:00 pm-7:55 pm

2 stops9h 55m

$378

OaklandWashington, D.C.

OAK - IAD

OAKIAD

Oakland

Wed 8/26

12:33 pm-11:39 pm

1 stop8h 06m

Washington, D.C. Dulles Intl

Tue 9/1

8:28 am-4:14 pm

2 stops10h 46m

$382
Quickest round-trip

OaklandPhiladelphia

OAK - PHL

OAKPHL

Oakland

Wed 7/22

2:40 pm-1:05 am

1 stop7h 25m

Philadelphia

Tue 7/28

5:15 am-9:45 am

1 stop7h 30m

$393

OaklandWashington, D.C.

OAK - IAD

OAKIAD

Oakland

Tue 9/22

6:48 am-6:14 pm

1 stop8h 26m

Washington, D.C. Dulles Intl

Sat 9/26

7:00 am-1:19 pm

1 stop9h 19m

$397

OaklandWashington, D.C.

OAK - DCA

OAKDCA

Oakland

Tue 9/22

1:29 pm-5:59 pm

2 stops25h 30m

Washington, D.C. Reagan-National

Sat 9/26

10:59 am-6:12 pm

1 stop10h 13m

$407

OaklandBaltimore

OAK - BWI

OAKBWI

Oakland

Tue 7/7

5:45 pm-5:45 am

1 stop9h 00m

Baltimore/Washington

Tue 7/14

8:05 am-2:05 pm

1 stop9h 00m

$411

OaklandWashington, D.C.

OAK - IAD

OAKIAD

Oakland

Wed 10/14

7:00 am-5:53 pm

1 stop7h 53m

Washington, D.C. Dulles Intl

Sun 10/18

7:24 pm-11:25 am

1 stop19h 01m

$412

OaklandBaltimore

OAK - BWI

OAKBWI

Oakland

Wed 9/9

7:45 pm-6:30 am

1 stop7h 45m

Baltimore/Washington

Sun 9/13

6:40 am-11:10 am

1 stop7h 30m

$417

OaklandWashington, D.C.

OAK - IAD

OAKIAD

Oakland

Wed 8/12

6:49 am-6:45 pm

1 stop8h 56m

Washington, D.C. Dulles Intl

Sun 8/16

6:03 am-9:26 am

1 stop30h 23m

$427

OaklandPhiladelphia

OAK - PHL

OAKPHL

Oakland

Wed 9/16

11:40 am-11:50 pm

2 stops9h 10m

Philadelphia

Sun 9/20

11:50 am-7:55 pm

2 stops11h 05m

$433

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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, October is the cheapest month in which you can book a flight from Oakland, California to Maryland (average of $199). Flying from Oakland, California to Maryland in January is currently the most expensive (average of $531). 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.

How much does it cost to fly round-trip from Oakland, California to Maryland?

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 June 15, 2026.
Peruse reviews from past customers who have flown with Southwest 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
4,235 reviews

Overall

7.9

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
Southwest
7.9
Good
4,235 reviews
Southwest
7.9
Good
4,235 reviews

Overall

7.9

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

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 $382, Southwest can have you in Maryland from Oakland, California in 8h 06m. Airlines will cover a distance of 2402 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, October is the cheapest month in which you can book a flight from Oakland, California to Maryland (average of $199). Flying from Oakland, California to Maryland in January is currently the most expensive (average of $531). 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 airline flying from Oakland to Maryland

Discover the top airline 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 June 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$353Average$470FlexibilityNo cancel feeOn-time63%

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