$89 Find Cheap Flights from Boston to Annapolis - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Annapolis departing on 8/22. 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.
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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$176
Typical prices: $187-$376
Delta
Sat 9/5Mon 9/7
BOS - BWI • Non-stop
Cheapest non-stop
$176
Typical prices: $190-$380
Southwest
Sat 9/5Fri 9/11
BOS - BWI • Non-stop
Arrival airport
You can't fly directly to Annapolis. It is served by Washington, D.C. (WAS), located 29.8 miles from Annapolis.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Boston to Annapolis (BOS-WAS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Annapolis 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 Boston to Annapolis

Sat, Sep 5 - Mon, Sep 7
Delta Logo
5:10 pm - 7:07 pm
BOS
-
BWI
1h 57mnonstop
Delta Logo
9:00 am - 10:38 am
BWI
-
BOS
1h 38mnonstop
$176Delta
Sat, Jul 18 - Tue, Jul 21
Delta Logo
5:05 pm - 7:02 pm
BOS
-
BWI
1h 57mnonstop
Delta Logo
6:21 am - 8:00 am
BWI
-
BOS
1h 39mnonstop
$177Delta
Wed, Jul 22 - Sun, Jul 26
JetBlue Logo
5:10 pm - 6:58 pm
BOS
-
DCA
1h 48mnonstop
JetBlue Logo
8:44 am - 10:20 am
DCA
-
BOS
1h 36mnonstop
$179JetBlue
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
8:55 pm - 10:35 pm
BOS
-
BWI
1h 40mnonstop
Southwest Logo
6:30 am - 8:00 am
BWI
-
BOS
1h 30mnonstop
$179Southwest
Sun, Sep 27 - Wed, Sep 30
United Airlines Logo
5:45 am - 7:20 am
BOS
-
IAD
1h 35mnonstop
United Airlines Logo
10:15 pm - 11:59 pm
IAD
-
BOS
1h 44mnonstop
$181United Airlines
Sat, Jul 25 - Wed, Aug 5
United Airlines Logo
5:45 am - 7:23 am
BOS
-
IAD
1h 38mnonstop
United Airlines Logo
8:25 am - 1:16 pm
IAD
-
BOS
4h 51m
1 stop
$182United Airlines
Mon, Jul 20 - Tue, Jul 28
Delta Logo
9:48 pm - 11:44 pm
BOS
-
DCA
1h 56mnonstop
Delta Logo
5:00 pm - 6:54 pm
DCA
-
BOS
1h 54mnonstop
$182Delta
Sun, Sep 13 - Wed, Sep 16
American Airlines Logo
7:00 am - 10:44 am
BOS
-
DCA
3h 44m
1 stop
American Airlines Logo
6:56 am - 8:45 am
DCA
-
BOS
1h 49mnonstop
$193American Airlines
Thu, Aug 6 - Sun, Aug 9
JetBlue Logo
10:20 am - 12:01 pm
BOS
-
DCA
1h 41mnonstop
JetBlue Logo
7:59 pm - 9:38 pm
DCA
-
BOS
1h 39mnonstop
$198JetBlue
Thu, Aug 6 - Sun, Aug 9
Southwest Logo
8:55 pm - 10:35 pm
BOS
-
BWI
1h 40mnonstop
Southwest Logo
7:10 am - 8:40 am
BWI
-
BOS
1h 30mnonstop
$207Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$89
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Boston to Baltimore

When to book flights from Boston to Annapolis

Are your dates flexible? Find out the best times to travel from Boston to Annapolis based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Boston to Annapolis

  • Which airports will I be using when flying from Boston to Annapolis?

    When flying out of Boston you’ll be using Boston Logan Intl. Annapolis does not have its own airport so you’ll be flying into nearby Washington, D.C. All airports airport, which is 29.8 mi away.

  • What’s the cheapest day of the week to fly between Boston and Annapolis?

    Consider leaving on a Friday and avoid Saturdays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Fridays and the most expensive ones on Saturdays.

  • How does KAYAK find such low prices on flights from Boston to Annapolis?

    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 Boston to Annapolis.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Annapolis from Boston 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 Boston to Annapolis?

    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 to Annapolis with an airline and back to Boston with another airline.

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

    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 to Annapolis from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Boston to Annapolis?

    In the last 5 days, the cheapest one-way ticket between Boston and Annapolis found on KAYAK was with JetBlue for $73. Delta offered a round-trip connection from $84 and United Airlines from $118.

Top tips for finding cheap flights from Boston to Annapolis

  • There is no airport in Annapolis. Instead, you’ll be flying into Washington, D.C. All airports when flying between Boston and Annapolis.
  • The cheapest flight from Boston to Annapolis was found 37 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be May, June and July. The cheapest month to fly is September.

Reviews of the top 5 airlines serving Boston to Annapolis

 
Need help choosing which airline to fly with from Boston to Annapolis? 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 4246 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

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!

2.0 MediocreDawn, Jun 2026
BUF - BWI
Read more Southwest reviews

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!

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.

I liked it better when you were truer to your roots Am paying more for less fun

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

WiFi was not working and didn’t have a beverage service

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

The flight was smooth, the crew was great but the plane was quite old

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

The flight was delayed, they didn’t even have water for the toilets or for drinks

It’s always a great time flying with united airlines.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

Attendants zipped through cabin so fast hardly anyone got the water they told us we could have in the short flight. Nothing else was offered.

Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

Great experience. Good dinner and service. FA's were very nice and attentive.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

The business steward was absolutely amazing! Smiles and kindness! Wish all AA flights are like this one!

Never going to fly your airline again if it can be avoided.

Worst experience ever. Flight could not land in Charlotte for what we were told was a ground stop. Had to be diverted to Raleigh to refuel. Strangely during ground stop, our connecting flight had no issue taking off on time causing us to miss our flight. We were told there were no other flights that day to our final destination and that two days out was the next one. The only flights to get us there were from Chicago the next morning. Completely opposite direction but it was a direct flight. So we get flown to Chicago and have to find a hotel in our own dime. The flight in the morning was also delayed. Thankfully only a short time. The non too of all this, our luggage did not arrive by the time we were there. Communication was terrible, through the entire trip. Complete incompetence. Will never fly American again.

Flight left 2 hours late with no explanation as to the delay

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

It was fine for what it was. It’s not luxury travel but it was efficient, for the most part. Having my carry-on transferred into luggage however, was unwelcome.

We had better-than-average leg room and I loved the access to shows and movies. During boarding, we could not hear the agent even though we were close to the boarding door, which was kind of scary when we realized that half of the passengers had already boarded. Also, the entertainment was awesome, but I could not hear the movie as well as I would have liked, because my headphones were crappy. It would have been better if I could connect my own ear buds via Bluetooth or if JetBlue provided headphones.

I was seated next to an autistic child who was out of control and had a child behind me kicking my seat for most of the trip. I will never fly JetBlue again. Ever. I don't care how cheap it is. It's terrible.

Great price, easy check in, love the free drinks and snacks, and nice crew. The only negative part was waiting for your seat assignment 5 minutes before boarding, and the seats are a bit uncomfortable.

What a great flight. Seats were more comfortable than other airlines. Flight was full but very easy to navigate. No stress no drama

All airline travel outside of First or Business class is an ordeal to be endured. This trip was ok, small o, small k.

Everything you need to know for your flight from Boston to Annapolis

Complete your trip to Annapolis with a hotel stay or car rental