$161 Find Cheap Flights from Oakland to Maryland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Oakland to Maryland departing on 9/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Maryland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oakland to Maryland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oakland to Maryland, as well as popular online travel agencies
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Flight Deals

Book Cheap Oakland to Maryland Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Oakland to Maryland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Oakland to Maryland

Tue, Aug 25 - Tue, Sep 1
Alaska Airlines Logo
2:11 pm - 6:30 am
OAK
-
BWI
13h 19m
1 stop
Alaska Airlines Logo
4:43 pm - 12:49 pm
BWI
-
OAK
23h 06m
1 stop
$361Alaska Airlines
Wed, Aug 26 - Wed, Sep 2
Frontier Logo
12:13 pm - 7:50 am
OAK
-
IAD
16h 37m
1 stop
Frontier Logo
9:20 am - 11:18 am
IAD
-
OAK
28h 58m
1 stop
$363Frontier
Fri, Nov 13 - Mon, Nov 16
Alaska Airlines Logo
7:42 pm - 4:49 pm
OAK
-
PHL
18h 07m
1 stop
Alaska Airlines Logo
4:25 pm - 9:36 am
PHL
-
OAK
20h 11m
1 stop
$369Alaska Airlines
Wed, Aug 19 - Wed, Aug 26
Southwest Logo
11:55 am - 10:20 pm
OAK
-
DCA
7h 25m
1 stop
Southwest Logo
6:40 pm - 11:05 pm
DCA
-
OAK
7h 25m
1 stop
$372Southwest
Fri, Aug 21 - Mon, Aug 24
Delta Logo
5:00 pm - 6:05 am
OAK
-
PHL
10h 05m
1 stop
Delta Logo
5:20 pm - 11:56 pm
PHL
-
OAK
9h 36m
2 stops
$374Delta
Wed, Aug 26 - Sat, Aug 29
Delta Logo
12:33 pm - 11:39 pm
OAK
-
IAD
8h 06m
1 stop
Delta Logo
7:00 am - 11:52 am
IAD
-
OAK
7h 52m
1 stop
$377Delta
Tue, Aug 25 - Wed, Sep 2
Delta Logo
6:00 am - 4:44 pm
OAK
-
DCA
7h 44m
1 stop
Delta Logo
5:54 pm - 10:38 pm
DCA
-
OAK
7h 44m
1 stop
$377Delta
Wed, Sep 16 - Mon, Sep 21
Southwest Logo
11:40 am - 11:50 pm
OAK
-
PHL
9h 10m
2 stops
Southwest Logo
4:05 pm - 10:25 pm
PHL
-
OAK
9h 20m
2 stops
$379Southwest
Thu, Sep 17 - Tue, Sep 22
Alaska Airlines Logo
11:55 am - 3:40 pm
OAK
-
BWI
24h 45m
1 stop
Alaska Airlines Logo
4:43 pm - 12:49 pm
BWI
-
OAK
23h 06m
1 stop
$379Alaska Airlines
Wed, Aug 26 - Tue, Sep 1
Delta Logo
12:33 pm - 11:39 pm
OAK
-
IAD
8h 06m
1 stop
Delta Logo
8:28 am - 4:14 pm
IAD
-
OAK
10h 46m
2 stops
$382Delta
Booking Insights

KAYAK's insights & trends for Oakland to Maryland flights

Get data-powered insights and trends into flights from Oakland to Maryland to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Oakland, California to Maryland?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Oakland, California to Maryland departing in August.

What is the cheapest month to fly from Oakland to Maryland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oakland to Maryland, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Oakland to Maryland is October, when tickets cost $199 (return) on average. On the other hand, the most expensive months are January and February, when the average cost of round-trip tickets is $531 and $466 respectively.

Good to know

Low seasonAugust
Cheapest flight$161
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Oakland to Baltimore

FAQs - booking Maryland flights

  • How does KAYAK find such low prices on flights from Oakland to Maryland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Oakland to Maryland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oakland to Maryland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oakland to Maryland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Oakland to Maryland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Oakland to Maryland with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oakland to Maryland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Oakland to Maryland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Oakland to Maryland

 
See real verified KAYAK customer reviews for airlines flying from Oakland to Maryland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Oakland to Maryland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4237 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

4.0 OkaySteven, Jun 2026
ONT - LAS
Read more Southwest reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Everything you need to know for your flight from Oakland to Maryland

Information on your arrival and departure airports