Find flights
When to book
FAQs & Tips
Airlines
Deals

Find cheap flights from Boston to Annapolis from $37

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 6/17. 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
Wed 7/10
Wed 7/17

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

In the last 7 days travelers have searched 42,898,604 times on KAYAK, and here is why:

Save 21% 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.

Good to know

Low season

January

High season

May

Cheapest flight

$37
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 17% 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?

    100 direct flights run between Boston and Annapolis on a daily basis. On average, there are about 706 departures each week.

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

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

  • 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 $37. Spirit Airlines offered a round-trip connection from $55 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 10295 reviews
8.2Boarding
8.6Crew
7.9Comfort
7.4Food
8.0Entertainment
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

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!

Overall fine but both ways for this trip was delayed.

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.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

Original plane sidelined. Had to wait an hour for replacement.

Crew was very cooperative and professional. Passenger's first checked in bag should be free.

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

Horrible, the flights kept delaying, so it is obvious that we won't be able to make it to the next connection. No easier/real agent on site to help you figure this out. UA agent on other counters refuse to assist you and direct us to use the QR code/call customer service. So inefficient and poor. While technology seems convenient, but it's not the best interest/experience for customers need help while there is active issue need assistance.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

My window shade didn’t work. So I missed coming into my city. ☹️

Flight was delayed in the gate by 5 hours and ultimately cancelled- rebooking service by United agents was terrible

Flight was delayed due to the late arrival of the catering truck, which is quite unacceptable. There was a beverage service, but no pretzel, or cookie, or nuts were served in coach.

Not worth the price of premium class ticket paid, felt more like steerage.

Paid for premium economy had no tv the whole time the crew tried to reset/reboot but would not work they said they would put a trouble ticket in for it. We had 3 seats my tv was the only one that didn't work. They cancelled our flight re worked us on another that left us at airport over night on the floor I have a ten year old and a 78 diabetic mother which also had shingles and suffers from nerve pain in legs and back. Requested wheelchair service at all airports after the re route NO wheelchair service was there to help. WORST experience we have ever had. Went to American airlines assistance it was closed. I AM FURIOUS!!! I expect some sort of compensation from this traumatic experience and no need for flying points we don't plan on using American airlines again!!!!

This is by far the worst experience I have had with American Airlines. The start of this trip was a complete disaster. I purposely planned my trip so that I would weather any delays so that I could make very important meeting at the Pentagon. My flight was cancelled because of maintenance and I was put on the first flight the next day but I was late to the meeting. After a long week at the Pentagon I just wanted to go home and my flight home which was early in the day was delayed. Eventually the flight was delayed until the next day. I was not authorized a hotel room because DCA was my point of origin. So I paid for a hotel out of pocket. The flight this morning was boarded then deplaned because the aircraft was hot. The flow of information was not happening in DCA and made it worse when the news was bad. I am going to take a break from American for my next few military flights. Hopefully whatever has been going on with American Airlines will be resolved.

We had a 2 hour delay. The seats were smaller than most other airlines. The person in front of us wanted to lay back and we had to stop her because she was pressing against my girlfriend’s legs. We had to ask her to sit up and not lay back due to the lack of room.

Everything was fine once we actually got on our flight. It was more then annoying they canceled (delayed) our flight. We lost out on a day of our trip along with money on our stay. Plus we had to book another hotel. So expensive.

This flight was canceled and delayed several times without explanation. The plane was freezing cold and no wifi for messaging. Getting off the plane was terribly unorganized and felt like it took forever….

The flight was delayed several times without explanation. The seats were terribly uncomfortable and wifi isn’t included. All these make for a less than ideal flight.

The flights was delayed by hours and it was the firmest landing I have experienced in my life. My back is still sore.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Terrible. I didn’t fly and I had an important meeting the next day.

Equipment swap led to 2+ hour delay on international flight. And to top it off, boarding took forever.

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

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.

Book cheap flights from Boston to Annapolis

Recent round-trip flight deals

7/9Tue
nonstopSpirit Airlines
1h 28mBOS-BWI
7/16Tue
nonstopSpirit Airlines
1h 33mBWI-BOS
$55
9/26Thu
nonstopSpirit Airlines
1h 31mBOS-BWI
10/1Tue
nonstopSpirit Airlines
1h 29mBWI-BOS
$61
7/10Wed
nonstopJetBlue
1h 39mBOS-DCA
7/10Wed
nonstopJetBlue
1h 44mDCA-BOS
$133
7/11Thu
nonstopJetBlue
1h 44mBOS-DCA
7/15Mon
nonstopJetBlue
1h 36mDCA-BOS
$139
6/30Sun
nonstopUnited Airlines
1h 41mBOS-IAD
7/5Fri
nonstopUnited Airlines
1h 38mIAD-BOS
$139
7/26Fri
nonstopUnited Airlines
1h 41mBOS-IAD
7/29Mon
1 stopUnited Airlines
5h 14mIAD-BOS
$149
6/21Fri
nonstopDelta
1h 48mBOS-DCA
6/26Wed
nonstopDelta
1h 38mDCA-BOS
$167
7/11Thu
nonstopAmerican Airlines
1h 50mBOS-DCA
7/14Sun
nonstopAmerican Airlines
1h 52mDCA-BOS
$168
7/26Fri
nonstopAmerican Airlines
1h 47mBOS-DCA
7/28Sun
nonstopAmerican Airlines
1h 52mDCA-BOS
$182
7/9Tue
nonstopDelta
1h 49mBOS-DCA
7/16Tue
1 stopDelta
4h 24mDCA-BOS
$192

Search by stops

Search by airline

Search by price

Recent one-way flight deals

6/17Mon
nonstopSpirit Airlines
1h 28mBOS-BWI
$37
6/17Mon
nonstopSpirit Airlines
1h 28mBOS-BWI
$38
8/8Thu
nonstopAmerican Airlines
1h 53mBOS-DCA
$69
7/10Wed
nonstopDelta
1h 52mBOS-DCA
$70
7/19Fri
nonstopUnited Airlines
1h 41mBOS-IAD
$70
8/24Sat
1 stopUnited Airlines
4h 10mBOS-IAD
$79
8/14Wed
nonstopDelta
1h 39mBOS-BWI
$83
6/27Thu
nonstopJetBlue
1h 42mBOS-DCA
$84
6/30Sun
nonstopAmerican Airlines
1h 53mBOS-DCA
$85
7/20Sat
nonstopJetBlue
1h 44mBOS-DCA
$90

Search by stops

Search by airline

Search by price

Last minute flights from Boston to Annapolis

Last minute flight, train and bus deals

6/14Fri
nonstopSpirit Airlines
1h 28mBOS-BWI
6/17Mon
nonstopSpirit Airlines
1h 33mBWI-BOS
$114
6/14Fri
nonstopSpirit Airlines
1h 28mBOS-BWI
6/24Mon
nonstopSpirit Airlines
1h 31mBWI-BOS
$119
6/14Fri
nonstopJetBlue
1h 39mBOS-DCA
7/16Tue
nonstopJetBlue
1h 36mDCA-BOS
$219
6/14Fri
nonstopUnited Airlines
1h 41mBOS-IAD
7/16Tue
nonstopUnited Airlines
1h 38mIAD-BOS
$219
6/14Fri
multi-stopDelta
4h 30mBOS-DCA
7/16Tue
nonstopDelta
1h 44mDCA-BOS
$229
6/14Fri
nonstopUnited Airlines
1h 41mBOS-IAD
7/16Tue
multi-stopUnited Airlines
4h 45mIAD-BOS
$229
6/13Thu
nonstopJetBlue
1h 40mBOS-DCA
6/17Mon
nonstopJetBlue
1h 44mDCA-BOS
$232
6/14Fri
nonstopDelta
1h 43mBOS-DCA
6/18Tue
nonstopDelta
1h 47mDCA-BOS
$233
6/15Sat
nonstopAmerican Airlines
1h 48mBOS-DCA
6/16Sun
nonstopAmerican Airlines
1h 34mDCA-BOS
$237
6/14Fri
nonstopAmerican Airlines
1h 44mBOS-DCA
6/16Sun
nonstopAmerican Airlines
1h 34mDCA-BOS
$303

Search by stops

Search by airline

Search by price

Flights to Annapolis