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Find cheap flights from Boston to Annapolis from $39

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Annapolis departing on 9/10. 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
0 bags
Thu 6/27
Thu 7/4

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Good to know

Low season

January

High season

May

Cheapest flight

$39
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 16% 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.

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

    Direct flights cover the 396 miles separating Boston and Annapolis in about 1h 28m.

  • How many flights are there between Boston and Annapolis?

    115 direct flights run between Boston and Annapolis on a daily basis. On average, there are about 808 departures each week.

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

    Consider leaving on a Tuesday and avoid Wednesdays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Thursdays 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 Spirit Airlines for $43. Spirit Airlines offered a round-trip connection from $39 and JetBlue from $133.

See more FAQs

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 65 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 March, April and May. The cheapest month to fly is January.
See more tips

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.
8.0
DeltaOverall score based on 10502 reviews
8.6Crew
8.2Boarding
7.4Food
7.9Comfort
8.0Entertainment
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

I had back trouble prior to my flight and everyone was great about helping me.

My tv was broken on the flight which is disappointing when you pay for a seat and expect a service

Always delays from Boston to Salt lake but this time was very long. Don’t understand while they board the passengers and then make them sit in the plane

Service for food to our seat was a bit slow. Snack choices were just pretzels or baked chips. My seat cushion was not attached. Other than Barbie, video choice were not very good or current.

After we landed, we were held on the plane for 30 minutes. There was no one at the gate once we landed and we forced to sit on a plan that had already over an hour delayed.

almost 4 hour delay as they over booked and had to wait for 8-10 volunteers to agree to travel next day.

Old plane. No outlets for laptop or phone. Seats worn out. Area around seat dirty.

I loved the flight and the crew. It was comfortable and smooth.

The crew was openly hostile and condescending to the customers. They spent the majority of that time in the rear talking and seemed really agitated when people asked questions. I heard five different people told that the information they requested was in the handout or safety brief.

ticketing issues caused many customers to have to go back to check in after waiting in security, then go through security line again.

Dinner was okay but the breakfast was not eatable on the flight San Francisco to Zurich.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

The Wi-Fi was unavailable on this flight for some reason.

On time take off…US cabins look tired and need of refresh!

Fantastic. Smooth boarding with an infant. Never experienced it with any other carriers.

This was a Lufthansa flight, not United. The CSA at the counter, Ashley, was not only incompetent, but quite rude. Me and two other PAX waited over 7 minutes standing in front of her and another CSA and they ignored us. We joked that we must have accidently taken invisibility pills. She could have at least said "I'll be with you in a moment, I'm currently....". I could go on about how rude she and the other CSAs were (whispering, not communicating with me, blaming the situation on others, etc.). She would not work for me. Then, she gave me literally the worst seat on the plane. the worst. My seat kept getting bumped (rammed twice by the crew with their carts and about every 5 minutes by someone using the bathroom), listening to the bathroom all night, crowded seat, etc.

My seat was broken. WiFi didn’t work. Gate crew at HOU were rude and condescending. Treated all the passengers badly. Bad experience, United.

First flight of the day… MINIMUM FUEL! 15 minute landing delay at HOU due to fog turned into a 2+ hour delay! Rather than circle, they had to divert to another city to refuel! Sat on tarmac at Austin to refuel. We ALL missed our connections! The crew, including pilots, were clueless. Crew was really a mess. At HOU, Untied employees were exceedingly rude to all. It was pitiful.

An hour and a half late is UNACCEPTABLE. The negative impact to our family is unconscionable. And for the price we were forced to pay...

No lounge access with “United First” ticket. False alarm about late flight, jeopardizing connection. Wrong meal. Loose power socket would not hold plug, could not charge device. In-flight access to text messaging did not work. Toilet seat on plane would not stay up.

The boarding process and flight were great. However, I waited about 40 minutes for my luggage. It did not come up on the designated belt. Instead, everyone’s bags were on a cart. Not sure what the issue was, but we were not informed until another passenger went looking for her bags and found them.

There were delays on both ends. It made it less than excellent. This plane was great though

AA1537 the AC was not working properly. It was very hot and uncomfortable.

Worst experience flying American Airlines. I fly with them often, so I was super disappointed in the service I received at gate 30 in LGA on May 24, mid-day. The flight was delayed twice. I was patiently waiting in the American Airlines lounge when I received the notice on my app that the plane was boarding 45 minutes before its newly re-scheduled take off of 4 pm (from the orginal 1:45 pm then 3:00 pm). It took me 5 min to travel from the lounge to the gate and when I arrived there at 3:20 flight gate attendant told me the flight had closed and that they announced for passengers multiple times. I showed them the notification on my app and they were really rude and unempathetic. The person who rescheduled my flight at customer service wasn't any happier but was at least helpful in getting me on the next flight.

Flight was 1/2 hour delayed leaving Phoenix. Otherwise it was an average flight. Flight crew on this trip was very nice.

Everything was great except for the wifi was junk. Crew was super friendly and helpful

Was lucky to have a employee at the AA checkin counter that had compassion and understood they ordeal that we went through with our original flight being diverted, needing to stay in the aircraft and then flying to the original destination; adding hours to the trip and forcing us to miss our connection and our rebooked connection. She was able to get up on standby on the highest priority on the next flight to the closest airport we need to be at and it all worked out despite being many hours late.

Delayed so that missed connecting flight. Connecting flight was also delayed on the tarmac but they closed the gate before the rescheduled time.

Attendants were rude. Scowling. Seats were miserable and we paid extra.

Took off over an hour late with multiple mechanical issues. Gate agent in Dallas was lazy and was slow as molasses. Had a line 10 people long. Spirit bad..

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

They seemingly have no respect for their customers, on any level. Avoid flying spirit, they will bump you to another flight without thinking twice so they can sell your seat, no joke.

One hour late taking off. Concerning, very hard landing. Uncomfortable seats with no recline. Extremely slow baggage claim. Very professional, knowledgeable flight attendants. Brand new, very clean plane.

We reached alomat 45 mins before but we were not allowed to checkin. I tried check in online 4 or 5 times but was always getting an error. The agents at Boston logan airport were very very rude and unwilling to help inspite of the fact that we were travelling with a small kid. Finally I was unable to checkin my bag and we ended up booking other airlines for Miami. Finally understood that we were unable to check in online coz we had a kid with us and we that when there is a kid, we have to check in at airport.

4 hour delay and hardly attempt to make it up. I might be stranded in Vegas tonight.

I liked that bag check was rather quick and efficient. The airplane chairs on the first leg of the trip were hard and uncomfortable. Also, the cabin temperature was too cold. The lady giving seat assignments took entirely too long. She said she would call me back to the desk in 5 minutes, and she never called me back.

I would not recommend choosing Spirit Airlines, despite their seemingly low fares. Upon booking one’s flight, one must also pay for seating, carry-on bags, checked bags, snacks, Wi-Fi, and beverages, including water. One will also receive multiple solicitations to “bid“ for roomier seating among other obnoxious offers. Our flight was delayed due to weather and traffic, which is not the fault of the airline, but the staff and system were unable to communicate in an accurately and timely way. The gate information was not updated in real time. The gate crew and flight crew instructed us to reach out to customer service for assistance, which we did prior to departure, but Wi-Fi was not available on this flight, so once in the air, we were not able to prepare for any connection issues when we landed. I able to text with customer service prior to departure, but that representative did not have information about connecting flights and gates at other airports. The flight crew was unable to share gate information as we arrived at the connecting location. They did attempt to hold one connection for people traveling to Chicago. (there were 21 on board), but when those people deplaned, the flight they were told had been held for them had not actually been held. We were all herded to a customer service desk with only two individuals to manage it. Most of the crew throughout the day did not seem to have training in how to work with tired and stressed travelers, and they did not use any de-escalation techniques. As a result, there were four screaming matches at the customer service desk we were sitting near during the five hours we waited to make a standby connection. At one point a gate agent and passenger were screaming at one another across the entire gate area. The second flight was also delayed (once again a result of a challenging weather day), but when the crew arrived to inspect the aircraft, there was a fight among crew members that was audible from the gate. At one point a manager ran in and closed the door so we could not hear our “professional“ crew screaming obscenities at one another. We were ultimately herded aboard and reached our destination at 3 AM. While the weather and airport traffic was out of everybody’s hands, the lack of communication and professionalism and the unsafe conditions (passenger and crew tempers were raging) make me believe that Spirit Airlines is not a safe or reasonable choice. Once all the additional fees are added, it is as economical and much more pleasant to fly another airline.

The Spirit travel experience was exceptional during the peak holiday season. The flight was on time and the service was exceptional.

Turbulence Lady at ticket counter who “took care of me was completely horrible and super disrespectful And staff on plane looked like they hate their job

Book cheap flights from Boston to Annapolis

Recent round-trip flight deals

9/10Tue
nonstopSpirit Airlines
1h 36mBOS-BWI
9/11Wed
nonstopSpirit Airlines
1h 26mBWI-BOS
$39
6/11Tue
nonstopSpirit Airlines
1h 28mBOS-BWI
6/11Tue
nonstopSpirit Airlines
1h 31mBWI-BOS
$40
6/18Tue
nonstopJetBlue
1h 42mBOS-DCA
6/18Tue
nonstopJetBlue
1h 48mDCA-BOS
$133
7/3Wed
nonstopDelta
1h 47mBOS-DCA
7/5Fri
nonstopDelta
1h 42mDCA-BOS
$139
6/18Tue
nonstopUnited Airlines
1h 41mBOS-IAD
6/21Fri
nonstopUnited Airlines
1h 36mIAD-BOS
$139
6/20Thu
nonstopDelta
1h 47mBOS-DCA
6/24Mon
nonstopDelta
1h 40mDCA-BOS
$140
6/17Mon
nonstopUnited Airlines
1h 44mBOS-IAD
6/19Wed
1 stopUnited Airlines
4h 40mIAD-BOS
$149
7/3Wed
nonstopJetBlue
1h 44mBOS-DCA
7/3Wed
nonstopJetBlue
1h 40mDCA-BOS
$153
6/22Sat
nonstopAmerican Airlines
1h 48mBOS-DCA
6/25Tue
nonstopAmerican Airlines
1h 34mDCA-BOS
$168
10/25Fri
nonstopAmerican Airlines
1h 50mBOS-DCA
10/28Mon
nonstopAmerican Airlines
1h 35mDCA-BOS
$188

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Recent one-way flight deals

6/8Sat
nonstopSpirit Airlines
1h 28mBOS-BWI
$43
6/5Wed
1 stopSpirit Airlines
8h 09mBOS-BWI
$44
8/31Sat
nonstopDelta
1h 46mBOS-DCA
$70
7/1Mon
nonstopUnited Airlines
1h 41mBOS-IAD
$70
8/26Mon
1 stopUnited Airlines
4h 05mBOS-IAD
$79
6/7Fri
nonstopDelta
1h 48mBOS-DCA
$90
8/6Tue
1 stopAmerican Airlines
5h 31mBOS-BWI
$91
6/17Mon
1 stopAmerican Airlines
4h 38mBOS-BWI
$115
7/7Sun
nonstopJetBlue
1h 44mBOS-DCA
$144
8/10Sat
nonstopJetBlue
1h 44mBOS-DCA
$179

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Last minute flights from Boston to Annapolis

Last minute flight, train and bus deals

6/2Sun
nonstopSpirit Airlines
1h 34mBOS-BWI
6/5Wed
nonstopSpirit Airlines
1h 31mBWI-BOS
$107
5/31Fri
nonstopSpirit Airlines
1h 34mBOS-BWI
6/5Wed
nonstopSpirit Airlines
1h 33mBWI-BOS
$108
5/31Fri
nonstopJetBlue
1h 41mBOS-DCA
6/2Sun
nonstopJetBlue
1h 31mDCA-BOS
$239
5/31Fri
nonstopUnited Airlines
1h 41mBOS-IAD
6/6Thu
nonstopUnited Airlines
1h 40mIAD-BOS
$239
6/2Sun
nonstopJetBlue
1h 51mBOS-DCA
6/3Mon
nonstopJetBlue
1h 39mDCA-BOS
$248
5/31Fri
multi-stopDelta
5h 56mBOS-DCA
6/4Tue
nonstopDelta
1h 43mDCA-BOS
$249
5/31Fri
nonstopUnited Airlines
1h 44mBOS-IAD
6/6Thu
multi-stopUnited Airlines
4h 40mIAD-BOS
$249
5/30Thu
nonstopAmerican Airlines
1h 50mBOS-DCA
6/2Sun
nonstopAmerican Airlines
1h 35mDCA-BOS
$258
5/31Fri
multi-stopDelta
3h 51mBOS-IAD
6/3Mon
multi-stopDelta
5h 59mIAD-BOS
$283
5/29Wed
multi-stopAmerican Airlines
19h 30mBOS-DCA
5/30Thu
nonstopAmerican Airlines
1h 34mDCA-BOS
$432

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Flights to Annapolis