$89 Find Cheap Flights from Boston to Annapolis

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 4/22. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights from Boston to Annapolis

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$169
Overall average: $273
United Airlines
Fri 5/29Tue 6/2
BOS - IAD • Non-stop
Cheapest one-way
$89
Typical prices: $111-$228
United Airlines
Wed 4/22
BOS - IAD • 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.
FAQs
FAQs
FAQs
FAQs
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Annapolis!
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

Fri, May 29 - Tue, Jun 2
United Airlines Logo
5:45 am - 7:23 am
BOS
-
IAD
1h 38mnonstop
United Airlines Logo
8:35 am - 10:20 am
IAD
-
BOS
1h 45mnonstop
$169United Airlines
Sat, May 9 - Tue, May 12
United Airlines Logo
7:10 pm - 11:25 pm
BOS
-
IAD
4h 15m
1 stop
United Airlines Logo
8:35 am - 10:18 am
IAD
-
BOS
1h 43mnonstop
$171United Airlines
Sun, May 3 - Sun, May 10
JetBlue Logo
6:20 am - 7:59 am
BOS
-
DCA
1h 39mnonstop
JetBlue Logo
9:00 pm - 10:38 pm
DCA
-
BOS
1h 38mnonstop
$171JetBlue
Fri, May 1 - Sun, May 3
JetBlue Logo
6:20 am - 7:59 am
BOS
-
DCA
1h 39mnonstop
JetBlue Logo
7:00 am - 8:34 am
DCA
-
BOS
1h 34mnonstop
$172JetBlue
Wed, Jun 10 - Mon, Jun 15
Delta Logo
1:15 pm - 3:07 pm
BOS
-
DCA
1h 52mnonstop
Delta Logo
9:59 pm - 11:38 pm
DCA
-
BOS
1h 39mnonstop
$174Delta
Thu, Apr 16 - Fri, Apr 17
Delta Logo
6:05 am - 8:05 am
BOS
-
DCA
2h 00mnonstop
Delta Logo
12:59 pm - 2:42 pm
DCA
-
BOS
1h 43mnonstop
$177Delta
Sat, May 2 - Sat, May 9
American Airlines Logo
8:00 am - 9:48 am
BOS
-
DCA
1h 48mnonstop
American Airlines Logo
10:00 pm - 11:39 pm
DCA
-
BOS
1h 39mnonstop
$180American Airlines
Mon, Apr 20 - Fri, Apr 24
Spirit Airlines Logo
8:16 pm - 9:15 am
BOS
-
BWI
12h 59m
1 stop
Spirit Airlines Logo
6:35 am - 7:58 am
BWI
-
BOS
1h 23mnonstop
$183Spirit Airlines
Tue, Apr 28 - Fri, May 1
American Airlines Logo
7:00 am - 8:46 am
BOS
-
DCA
1h 46mnonstop
American Airlines Logo
10:40 pm - 12:21 am
DCA
-
BOS
1h 41mnonstop
$184American Airlines
Thu, Apr 9 - Sun, Apr 19
Spirit Airlines Logo
4:23 pm - 11:59 pm
BOS
-
BWI
7h 36m
1 stop
Spirit Airlines Logo
6:35 am - 7:58 am
BWI
-
BOS
1h 23mnonstop
$186Spirit Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$89
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Boston to Washington Dulles Airport

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 Wednesday 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 72 hours, the cheapest one-way ticket between Boston and Annapolis found on KAYAK was with JetBlue for $68. Spirit Airlines offered a round-trip connection from $42 and Delta from $80.

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 86 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 October, November and December. 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
DeltaOverall score based on 8319 reviews
8.1Boarding
7.8Entertainment
7.9Comfort
8.5Crew
7.2Food
Airline reviews

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

2.0 MediocreSreekumar, Mar 2026
FLL - DTW
Read more Delta reviews

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

My flight was canceled a few hours before boarding. I was rebooked on Copa airlines and missed an important meeting .

Good quick flight on a small but comfortable plane. I'm 6'3 and had plenty of space.

Experience was great - no complaints. Took off on time, landed early. Got to the gate relatively quickly - took a little bit of extra time to deplane but nothing excessive.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

OK, we were delayed and had to de plane and reboard.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Both my flight where delayed Had 25min to make it to my transfer flight

Everything was on time and service on the flight was great!

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Worst customer service ever experienced on the planet, dirty plane, no communication, and severe delays

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Absolutely terrible. Would never fly American again. 2 deplaned incidents and delayed by close to 24 hours. $12 meal voucher for first class passengers was an insult to the injury. Pathetic.

Terrible planning. And even worse gate agents. Absolutely rude behavior.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

Flight was scheduled at 11:26am but they keep Delaying until midnight. They waited at airport restless.

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

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

It was great. Smooth flight, comfortable, left on time and landed on time.

We hoarded. Then we deplaned. Then we waited for 10 hours in the MSP airport due to a wheel misfunction. We understand safety but communication between crew and airport staff was horrible. When we did finally board, we were rushed on and because we were waiting for a “fresh” pilot and crew, we sat in a roasting plane with no A/C for an hour. My question is why was this flight not cancelled right away when they knew this would be a huge issue OR, why did AA not get a substitute plane, considering this was already a full flight? To me, this appears to be a complete breakdown in leadership and utter systems failure. The compensation for completely disrupting travel plans for hundreds, which we paid dearly for, was measly. While we appreciated the lodging for the night, $12 in meal vouchers isn’t going to sustain anyone for over 12 hours. “We apologize; our hands are tied” is no longer an acceptable explanation. We are so completely turned off by this experience and will definitely seek alternative avenues when we need to fly.

Mostly good. The WiFi wasn’t working so that was not great.

I rated the experience "mediocre" because of the 2 hour delay in take off. This is the 4th flight from DFW on AA where there was a delay and in one of the instances (after 13 delays), the flight was cancelled. I understand weather but for the March 18th flight, there was no weather issue in Dallas or Detroit. I called Concierge Key and they were wonderful, booking me on a later flight in case my flight was cancelled. I have flown with American for many years and never has there been this consistent pattern of delays. Very disappointing.

we boarded the plane and then sat for OVER AN HOUR on it, first waiting for fuel and then the crew timed out. the flight kept getting delayed longer and longer, a 9:30pm flight is still on the ground at 1:15am.

Delay due to personnel issues on Spirit’s end. Original departure time 9:30pm. Took off at 2:15am. Lost an entire night’s sleep bc Spirit couldn’t get a crew together. Very poor.

Not enough crew members so we had to wait for more to arrive and they could never give us updates timing. Not even water for free on board. Bare bones airplane- there wasn’t even a seat back pocket to put things into. Spirit is cheap for a reason but this was dismal

The bag situation was confusing. I didn’t know I had to pay for Carry ons. The seats were uncomfortable and there was no entertainment

4 hour delay, 2 hours in the airport and then 2 hours on the tarmac. With a flight full of kids it would have been better to leave us in the airport for the delay, it was crying kids chaos on the flight. Miserable. And no apology or airline credit for the significant delay.

They charged late fees for selecting seats (no $0 options). They also changed my gate within the last half hour and are refusing to reimburse my costs to drive across the country with two small children in a rental car.

Horrible we lost a day at the destination. Flight was canceled at 2am left us scrambling for another airline to get us to destination

The flight itself was great except for an air traffic controller delay. We left 30 min late but they made up most of the time in flight. The booking was frustrating, as we chose a certain flight and it was changed four times. We got to Orlando several hours later than the original flight we chose.

the fligh was delay form 9am to 10, delayed again from 10 to 11, than delay and gate change to 12 and delay another gate change to 3;25 pm

We had too many delays for the crew not the plane

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

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