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$77+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BWI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Oakland to Maryland

Keep the following information in mind while searching for Oakland to Maryland flight deals. Data was last updated September 11, 2025.

Round-trip from

$189
(Southwest)

One-way from

$77
(Southwest)

Popular in

December

Cheapest in

September

Average price

$389
From Oakland to Maryland
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One-way flight from Oakland to Maryland
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Highest demand for flights based on searches. 8% potential increase in price ($38 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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Find 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/9. 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 10/295:20 amOAK - DCA
1 stop9h 45mSouthwest
Wed 12/34:40 pmDCA - OAK
2 stops8h 40mSouthwest
Deal found 9/9$189
This Southwest deal was found by Cheapflights users on 9/10. 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.
Wed 12/177:50 amOAK - DCA
1 stop12h 05mSouthwest
Wed 1/144:40 pmDCA - OAK
1 stop7h 45mSouthwest
Deal found 9/10$199
This Trip.com deal was found by Cheapflights users on 9/8. 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.
Sat 9/276:30 amOAK - BWI
1 stop19h 00mSpirit Airlines
Tue 9/308:16 amBWI - OAK
1 stop18h 16mSpirit Airlines
Deal found 9/8$204
This Southwest deal was found by Cheapflights users on 9/11. 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.
Mon 11/108:00 amOAK - DCA
1 stop11h 00mSouthwest
Sat 11/1511:25 amDCA - OAK
1 stop8h 20mSouthwest
Deal found 9/11$204
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/246:30 amOAK - PHL
1 stop11h 21mSpirit Airlines
Mon 9/295:21 pmPHL - OAK
1 stop9h 11mSpirit Airlines
Deal found 9/11$223
This Southwest deal was found by Cheapflights users on 9/10. 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.
Tue 11/185:25 amOAK - IAD
1 stop8h 40mSouthwest
Sat 11/227:45 pmIAD - OAK
1 stop7h 50mSouthwest
Deal found 9/10$225
This Southwest deal was found by Cheapflights users on 9/11. 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.
Wed 11/56:30 pmOAK - BWI
1 stop8h 15mSouthwest
Sat 11/88:50 amBWI - OAK
1 stop11h 10mSouthwest
Deal found 9/11$230
This Southwest deal was found by Cheapflights users on 9/10. 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.
Thu 11/68:00 amOAK - DCA
1 stop11h 00mSouthwest
Wed 11/126:00 amDCA - OAK
1 stop11h 05mSouthwest
Deal found 9/10$231
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:30 amOAK - BWI
1 stop8h 27mSpirit Airlines
Mon 9/297:02 pmBWI - OAK
1 stop31h 30mSpirit Airlines
Deal found 9/10$237
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
Wed 10/16:30 amOAK - BWI
1 stop8h 27mSpirit Airlines
Thu 10/27:02 pmBWI - OAK
1 stop7h 30mSpirit Airlines
Deal found 9/9$240
This Southwest deal was found by Cheapflights users on 9/11. 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.
Wed 10/154:10 pmOAK - DCA
2 stops13h 45mSouthwest
Sat 10/187:25 amDCA - OAK
1 stop14h 30mSouthwest
Deal found 9/11$244
This Southwest deal was found by Cheapflights users on 9/9. 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 11/188:20 amOAK - DCA
2 stops9h 10mSouthwest
Sat 11/226:50 pmDCA - OAK
1 stop9h 40mSouthwest
Deal found 9/9$250

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 September 11, 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 12/17

7:50 am-10:55 pm

1 stop12h 05m

Washington, D.C. Reagan-National

Wed 1/14

4:40 pm-9:25 pm

1 stop7h 45m

$199

OaklandWashington, D.C.

OAK - DCA

OAKDCA

Oakland

Tue 11/18

8:20 am-8:30 pm

2 stops9h 10m

Washington, D.C. Reagan-National

Sat 11/22

6:50 pm-1:30 am

1 stop9h 40m

$250

OaklandBaltimore

OAK - BWI

OAKBWI

Oakland

Wed 9/24

10:56 am-4:30 am

2 stops14h 34m

Baltimore/Washington

Sat 9/27

8:16 am-11:32 pm

1 stop18h 16m

$262

OaklandWashington, D.C.

OAK - DCA

OAKDCA

Oakland

Fri 11/7

5:25 am-2:55 pm

1 stop6h 30m

Washington, D.C. Reagan-National

Thu 11/13

6:10 am-3:20 pm

1 stop12h 10m

$266

OaklandWashington, D.C.

OAK - IAD

OAKIAD

Oakland

Fri 10/3

6:35 am-5:40 pm

1 stop8h 05m

Washington, D.C. Dulles Intl

Tue 10/7

7:40 am-2:30 pm

2 stops9h 50m

$270

OaklandBaltimore

OAK - BWI

OAKBWI

Oakland

Thu 11/6

7:25 am-7:10 pm

1 stop8h 45m

Baltimore/Washington

Sun 11/9

2:40 pm-9:20 pm

1 stop9h 40m

$288

OaklandWashington, D.C.

OAK - DCA

OAKDCA

Oakland

Fri 11/14

8:00 am-10:00 pm

1 stop11h 00m

Washington, D.C. Reagan-National

Mon 11/17

12:55 pm-5:15 pm

1 stop7h 20m

$289

OaklandWashington, D.C.

OAK - DCA

OAKDCA

Oakland

Sun 10/5

6:10 am-10:50 pm

1 stop13h 40m

Washington, D.C. Reagan-National

Tue 10/7

12:35 pm-4:40 pm

1 stop7h 05m

$290

OaklandWashington, D.C.

OAK - IAD

OAKIAD

Oakland

Wed 2/11

6:30 am-5:55 pm

1 stop8h 25m

Washington, D.C. Dulles Intl

Sat 2/14

6:55 pm-9:08 am

1 stop17h 13m

$298

OaklandWashington, D.C.

OAK - DCA

OAKDCA

Oakland

Wed 2/11

10:10 am-9:55 pm

1 stop8h 45m

Washington, D.C. Reagan-National

Sat 2/14

5:10 pm-8:43 am

1 stop18h 33m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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, August is the cheapest month in which you can book a flight from Oakland, California to Maryland (average of $241). Flying from Oakland, California to Maryland in March is currently the most expensive (average of $290). 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 September 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oakland, California to Maryland as you normally would.

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 September 11, 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
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 $298, Southwest can have you in Maryland from Oakland, California in 8h 25m. 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 cheapest airlines to fly from Oakland, California to Maryland one-way?

    The cheapest airlines for a one-way flight from Oakland, California to Maryland are Southwest ($77), Spirit Airlines ($99), and Hawaiian Airlines ($122).

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

    The most popular route from Oakland, California to Maryland is Oakland - Baltimore/Washington. You may also consider Oakland - Washington, D.C. Dulles Intl 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, August is the cheapest month in which you can book a flight from Oakland, California to Maryland (average of $241). Flying from Oakland, California to Maryland in March is currently the most expensive (average of $290). 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.

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Alternative routes for Oakland to Maryland

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Top 4 airlines flying from Oakland to Maryland

Discover the top 4 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$154Average$486FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$169Average$290FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$204Average$469FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$362Average$486FlexibilityNo cancel feeOn-time63%

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