$76 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 11/21. 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

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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

Sun, Nov 2 - Tue, Nov 4
American Airlines Logo
5:00 am - 6:44 amBOS-DCA
1h 44mnonstop
American Airlines Logo
6:59 am - 8:47 amDCA-BOS
1h 48mnonstop
$154American Airlines
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Fri, Oct 31 - Sun, Nov 2
Frontier Logo
9:23 am - 8:16 pmBOS-BWI
10h 53m1 stop
Frontier Logo
8:21 pm - 8:28 amBWI-BOS
12h 07m1 stop
$154Frontier
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Thu, Oct 9 - Sat, Oct 11
United Airlines Logo
5:30 am - 7:11 amBOS-IAD
1h 41mnonstop
United Airlines Logo
10:19 pm - 11:59 pmIAD-BOS
1h 40mnonstop
$155United Airlines
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Tue, Oct 7 - Wed, Oct 8
United Airlines Logo
10:34 am - 4:05 pmBOS-IAD
5h 31m1 stop
United Airlines Logo
8:30 am - 1:25 pmIAD-BOS
4h 55m1 stop
$157United Airlines
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Fri, Oct 31 - Fri, Nov 7
JetBlue Logo
6:10 am - 7:56 amBOS-DCA
1h 46mnonstop
JetBlue Logo
4:55 pm - 11:48 pmDCA-BOS
6h 53m1 stop
$158JetBlue
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Thu, Oct 2 - Mon, Oct 6
JetBlue Logo
6:30 am - 8:09 amBOS-DCA
1h 39mnonstop
JetBlue Logo
5:20 pm - 12:14 amDCA-BOS
6h 54m1 stop
$161JetBlue
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Tue, Dec 30 - Mon, Jan 5
Delta Logo
9:00 am - 11:02 amBOS-DCA
2h 02mnonstop
Delta Logo
6:55 pm - 8:40 pmDCA-BOS
1h 45mnonstop
$162Delta
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Sat, Oct 4 - Wed, Oct 8
Spirit Airlines Logo
12:20 pm - 8:44 pmBOS-BWI
8h 24m1 stop
Spirit Airlines Logo
1:35 pm - 10:52 pmBWI-BOS
9h 17m1 stop
$165Spirit Airlines
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Tue, Oct 7 - Tue, Oct 14
Spirit Airlines Logo
6:16 am - 2:48 pmBOS-BWI
8h 32m1 stop
Spirit Airlines Logo
5:20 pm - 11:26 amBWI-BOS
18h 06m1 stop
$171Spirit Airlines
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Tue, Oct 7 - Wed, Oct 8
Delta Logo
3:48 pm - 5:34 pmBOS-BWI
1h 46mnonstop
Delta Logo
6:18 am - 8:00 amBWI-BOS
1h 42mnonstop
$177Delta
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Good to know

Low seasonAugust
Cheapest flight$76
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Boston to Reagan Washington National 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.

  • How long does a flight from Boston to Annapolis take?

    Direct flights cover the 396 miles separating Boston and Annapolis in about 1h 39m.

  • How many flights are there between Boston and Annapolis?

    118 direct flights run between Boston and Annapolis on a daily basis. On average, there are about 831 departures each week.

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

    Consider leaving on a Sunday and avoid Saturdays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Mondays 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 $76. American Airlines offered a round-trip connection from $154 and Frontier from $154.

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 35 days before departure, on average.
  • Book at least 1 week 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 January.

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 7957 reviews
7.9Comfort
8.2Boarding
7.3Food
8.5Crew
7.9Entertainment
Airline reviews

The staff and the boarding procedure were all amazing . The one flight was not equipped with WIFI which now adays seems odd. All in all the experience was good

8.0 ExcellentAnonymous, Sep 2025GFK - MSP
Read more Delta reviews

The staff and the boarding procedure were all amazing . The one flight was not equipped with WIFI which now adays seems odd. All in all the experience was good

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

Terrible. They wouldn't allow me on my flight on the 14th..

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Flight was good and crew was super polite. However, there were around 5 kids screaming the WHOLE 2 hours. I understand kids have to come but parents need to do something to control their children. They make the experience terrible, especially after finishing 16 hour shifts at the hospital I needed some sleep, which I did not get.

IAD with the archaic people movers is just a place to be avoided.

Tastless food and too obvious lack of enthusiasm for service in the economy vesus business class

All of the United employees I interacted with were professional and courteous. The aircraft was clean, the food on the flight was good. No complaints here.

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

I flew with my dog and had already purchased my dog’s ticket. Even that morning I had called costumer service to insure that my husband and I had seats together since the website was giving me an error when choosing our seats and the representative mentioned our dog. I showed up early to the airport and when I got to the gate and we started boarding I was help back and told that I was supposed to have a yellow tag and that I should have checked in at the counter for them to give me that tag. I was not aware of this, the representative on the phone did not say anything. Nor did I see it anywhere in the checking process online, so if you travel with a pet and are not checking in luggage, just know that you still have to go to the check in counter when arriving at the airport unless you want to be the last one to board and not have room for your carry on in the overhead bins. Other than that, I had a great experience.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

The entertainment package was vast and the selections were very current. Keep updating it was great.

The seat was so hard my tailbone was aching The crew was kind of a b**** because I made a joke that I didn't care if they close the door I total c*** when she was trying to f****** act like she was mad at me because I said that The flight was bumpy. Sure you didnt have control over that.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

Spirit rescheduled a 4:30 PM flight to 8:52 AM. That's ridiculous and borderline fraud.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

Cancelled my flight last minute and did not help me rebook. It was a horrible experience.

Had a issue with catching flight due to airline, was unable to board flight

Better than my las vagas experience, but still dissapointed with the airline support service.

I enjoyed my flight, it was pretty smooth and we landed earlier than eta.

Seats too hard, too much lumbar. Space between rows was extremely tight, so tight hard to place item under seat in front of me. No tv screens. Zero plugs for charging phones. Too many sales pitches

Flight was 2hours late they had no crew or the pilot.

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