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$119+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BWI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This CheapOair deal was found by Cheapflights users on 1/28. 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 2/256:15 am
OAK
-
IAD
1 stop8h 05m
Alaska Airlines
Wed 3/47:05 am
IAD
-
OAK
1 stop12h 32m
Alaska Airlines
Deal found 1/28$237
This Southwest deal was found by Cheapflights users on 1/28. 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 2/265:20 am
OAK
-
IAD
1 stop6h 25m
Southwest
Sat 2/285:05 am
IAD
-
OAK
1 stop8h 00m
Southwest
Deal found 1/28$257
This CheapOair deal was found by Cheapflights users on 1/26. 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.
Thu 2/266:15 am
OAK
-
IAD
1 stop8h 05m
Alaska Airlines
Tue 3/37:05 am
IAD
-
OAK
1 stop12h 32m
Alaska Airlines
Deal found 1/26$267
This CheapOair deal was found by Cheapflights users on 1/27. 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 3/36:15 am
OAK
-
IAD
1 stop8h 05m
Alaska Airlines
Wed 3/117:05 am
IAD
-
OAK
1 stop12h 32m
Alaska Airlines
Deal found 1/27$277
This CheapOair deal was found by Cheapflights users on 1/28. 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 4/76:40 pm
OAK
-
PHL
1 stop8h 25m
Alaska Airlines
Tue 4/146:47 pm
PHL
-
OAK
1 stop18h 46m
Alaska Airlines
Deal found 1/28$277
This Southwest deal was found by Cheapflights users on 1/26. 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 3/311:10 am
OAK
-
DCA
1 stop9h 10m
Southwest
Wed 3/46:00 am
DCA
-
OAK
1 stop14h 30m
Southwest
Deal found 1/26$283
This CheapOair deal was found by Cheapflights users on 1/26. 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.
Sat 2/216:15 am
OAK
-
IAD
1 stop8h 05m
Alaska Airlines
Tue 2/247:05 am
IAD
-
OAK
1 stop12h 32m
Alaska Airlines
Deal found 1/26$287
This Southwest deal was found by Cheapflights users on 1/26. 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 2/265:05 am
OAK
-
DCA
1 stop10h 05m
Southwest
Tue 3/39:30 am
DCA
-
OAK
1 stop7h 35m
Southwest
Deal found 1/26$292
This CheapOair deal was found by Cheapflights users on 1/28. 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 3/36:15 am
OAK
-
IAD
1 stop8h 05m
Alaska Airlines
Fri 3/66:20 pm
IAD
-
OAK
2 stops25h 17m
Alaska Airlines
Deal found 1/28$295
This CheapOair deal was found by Cheapflights users on 1/27. 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.
Thu 2/266:15 am
OAK
-
IAD
1 stop8h 05m
Alaska Airlines
Sat 2/287:05 am
IAD
-
OAK
1 stop12h 32m
Alaska Airlines
Deal found 1/27$297
This Southwest deal was found by Cheapflights users on 1/26. 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 3/37:25 pm
OAK
-
BWI
1 stop7h 20m
Southwest
Wed 3/410:25 am
BWI
-
OAK
1 stop10h 05m
Southwest
Deal found 1/26$297
This CheapOair deal was found by Cheapflights users on 1/28. 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 5/197:59 pm
OAK
-
IAD
1 stop8h 35m
Alaska Airlines
Tue 6/25:33 pm
IAD
-
OAK
1 stop9h 21m
Alaska Airlines
Deal found 1/28$307

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(CheapOair)

One-way from

$119
(CheapOair)

Popular in

December

Cheapest in

February

Average price

$424
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. 7% potential increase in price ($34 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 January 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 January 29, 2026.
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 - IAD

OAKIAD

Oakland

Wed 2/25

6:15 am-5:20 pm

1 stop8h 05m

Washington, D.C. Dulles Intl

Wed 3/4

7:05 am-4:37 pm

1 stop12h 32m

$237

OaklandWashington, D.C.

OAK - DCA

OAKDCA

Oakland

Tue 3/3

11:10 am-11:20 pm

1 stop9h 10m

Washington, D.C. Reagan-National

Wed 3/4

6:00 am-5:30 pm

1 stop14h 30m

$283

OaklandWashington, D.C.

OAK - DCA

OAKDCA

Oakland

Thu 2/26

5:05 am-6:10 pm

1 stop10h 05m

Washington, D.C. Reagan-National

Tue 3/3

9:30 am-2:05 pm

1 stop7h 35m

$292

OaklandWashington, D.C.

OAK - IAD

OAKIAD

Oakland

Mon 3/2

5:31 pm-5:40 am

1 stop9h 09m

Washington, D.C. Dulles Intl

Tue 3/3

7:05 am-4:37 pm

1 stop12h 32m

$297

OaklandBaltimore

OAK - BWI

OAKBWI

Oakland

Tue 3/3

6:15 am-5:15 pm

2 stops8h 00m

Baltimore/Washington

Wed 3/4

6:20 am-12:15 pm

1 stop8h 55m

$302

OaklandWashington, D.C.

OAK - IAD

OAKIAD

Oakland

Mon 3/2

4:59 pm-9:13 am

2 stops13h 14m

Washington, D.C. Dulles Intl

Tue 3/3

5:13 pm-11:51 pm

2 stops9h 38m

$308

OaklandPhiladelphia

OAK - PHL

OAKPHL

Oakland

Wed 4/22

5:04 pm-5:35 am

1 stop9h 31m

Philadelphia

Thu 4/30

6:54 pm-11:54 pm

1 stop8h 00m

$309

OaklandPhiladelphia

OAK - PHL

OAKPHL

Oakland

Mon 3/2

5:31 pm-5:20 pm

1 stop20h 49m

Philadelphia

Tue 3/10

6:22 pm-9:14 am

1 stop17h 52m

$309

OaklandPhiladelphia

OAK - PHL

OAKPHL

Oakland

Thu 3/5

5:55 am-5:38 pm

1 stop8h 43m

Philadelphia

Mon 3/9

6:49 pm-11:46 pm

1 stop7h 57m

$309

OaklandPhiladelphia

OAK - PHL

OAKPHL

Oakland

Tue 4/21

5:04 pm-5:35 am

1 stop9h 31m

Philadelphia

Wed 4/29

6:54 pm-11:54 pm

1 stop8h 00m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

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 $142). 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.

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 January 29, 2026.
Peruse reviews from past customers who have flown with Southwest 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
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

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
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

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
9,215 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

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 $237, Alaska Airlines can have you in Maryland from Oakland, California in 8h 05m. 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. Reagan-National. You may also consider Oakland - Washington, D.C. Dulles Intl or Oakland - Baltimore/Washington.

  • 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 $142). 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 2 airlines flying from Oakland to Maryland

Discover the top 2 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$353Average$479FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$377Average$531FlexibilityNo cancel feeOn-time69%

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