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$77+ Cheap flights from Boston (BOS) to Annapolis, MD

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — IAD
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Annapolis are usually found in January or March, booked 35 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap flight deals from Boston to Annapolis

Keep the following information in mind while searching for Boston to Annapolis flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$154
(American Airlines)

One-way from

$77
(Trip.com)

Popular in

November

Cheapest in

January

Average price

$197
From Boston Logan Intl to Annapolis
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One-way flight from Boston Logan Intl to Annapolis
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Highest demand for flights based on searches. 4% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Boston to Annapolis

Cheapest flights from Boston to Annapolis
Explore the most affordable flight options available from Boston to Annapolis. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/25:00 amBOS - DCA
Nonstop1h 44mAmerican Airlines
mar. 11/46:59 amDCA - BOS
Nonstop1h 48mAmerican Airlines
Deal found 9/14$154
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/319:23 amBOS - BWI
1 stop10h 53mFrontier
dom. 11/28:21 pmBWI - BOS
1 stop12h 07mFrontier
Deal found 9/14$154
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/95:30 amBOS - IAD
Nonstop1h 41mUnited Airlines
sáb. 10/1110:19 pmIAD - BOS
Nonstop1h 40mUnited Airlines
Deal found 9/16$155
This Priceline deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/412:20 pmBOS - BWI
1 stop8h 24mSpirit Airlines
sáb. 10/111:35 pmBWI - BOS
1 stop9h 17mSpirit Airlines
Deal found 9/14$156
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/710:34 amBOS - IAD
1 stop5h 31mUnited Airlines
mar. 10/148:30 amIAD - BOS
1 stop4h 55mUnited Airlines
Deal found 9/16$157
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/36:00 amBOS - DCA
1 stop4h 28mUnited Airlines
dom. 10/57:00 amDCA - BOS
1 stop4h 08mUnited Airlines
Deal found 9/15$157
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/2611:44 amBOS - BWI
1 stop23h 51mMultiple Airlines
mié. 10/291:35 pmBWI - BOS
1 stop9h 17mMultiple Airlines
Deal found 9/13$157
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/1512:10 pmBOS - IAD
1 stop3h 55mUnited Airlines
mié. 10/1510:19 pmIAD - BOS
Nonstop1h 40mUnited Airlines
Deal found 9/16$158
This lastminute.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/316:10 amBOS - DCA
Nonstop1h 46mJetBlue
vie. 11/74:55 pmDCA - BOS
1 stop6h 53mJetBlue
Deal found 9/16$158
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/165:30 amBOS - IAD
Nonstop1h 41mUnited Airlines
dom. 10/196:15 amIAD - BOS
1 stop4h 53mUnited Airlines
Deal found 9/16$159
This Rumbo deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/29:20 amBOS - DCA
Nonstop1h 55mJetBlue
lun. 10/65:20 pmDCA - BOS
1 stop6h 54mJetBlue
Deal found 9/14$159
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/249:18 amBOS - IAD
1 stop11h 55mFrontier
dom. 10/268:02 pmIAD - BOS
1 stop12h 31mFrontier
Deal found 9/14$160

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Annapolis that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 16, 2025.
Use the filters below to find and compare flights from Boston to Annapolis that are best for you.

Fly from

Boston

Fly to

Annapolis

Route

Depart

Return

Price

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

vie. 10/31

9:15 am-1:19 pm

1 stop4h 04m

Washington, D.C. Reagan-National

mié. 11/5

7:00 am-10:43 am

1 stop3h 43m

$157

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

sáb. 10/18

6:00 am-10:43 am

1 stop4h 43m

Washington, D.C. Reagan-National

mar. 10/21

10:33 am-4:22 pm

1 stop5h 49m

$157

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

mar. 10/21

8:00 am-12:19 pm

1 stop4h 19m

Washington, D.C. Reagan-National

lun. 11/3

7:00 pm-10:47 pm

1 stop3h 47m

$157

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

mar. 11/11

10:25 am-3:53 pm

1 stop5h 28m

Washington, D.C. Reagan-National

mié. 11/12

7:00 am-10:43 am

1 stop3h 43m

$157

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

mié. 10/15

5:30 am-7:11 am

Nonstop1h 41m

Washington, D.C. Dulles Intl

lun. 10/20

6:15 am-11:08 am

1 stop4h 53m

$158

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

vie. 11/21

5:30 am-7:13 am

Nonstop1h 43m

Washington, D.C. Dulles Intl

lun. 11/24

9:00 am-10:38 am

Nonstop1h 38m

$161

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

vie. 10/17

6:05 am-8:05 am

Nonstop2h 00m

Washington, D.C. Reagan-National

lun. 10/20

10:00 pm-11:40 pm

Nonstop1h 40m

$162

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

mié. 11/19

11:59 am-4:25 pm

1 stop4h 26m

Washington, D.C. Dulles Intl

dom. 11/23

8:45 am-12:28 pm

1 stop3h 43m

$172

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

mié. 11/19

1:30 pm-5:25 pm

1 stop3h 55m

Washington, D.C. Reagan-National

dom. 11/23

10:05 am-3:17 pm

1 stop5h 12m

$172

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

mié. 10/8

10:34 am-4:05 pm

1 stop5h 31m

Washington, D.C. Dulles Intl

mié. 10/15

6:15 am-11:08 am

1 stop4h 53m

$173

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 57 results
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Best time to book a flight from Boston to Annapolis

Have a flexible travel schedule? Discover the best time to fly to Annapolis from Boston with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Boston to Annapolis?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Annapolis. Price data was last updated on September 12, 2025.

To ensure you get the cheapest price possible for a flight from Boston to Annapolis, you should look to book at least 35 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Boston to Annapolis?

Currently, August is the cheapest month in which you can book a flight from Boston to Annapolis (average of $292). Flying from Boston to Annapolis in April is currently the most expensive (average of $337). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from BOS to AP9?

Find hourly flight availability from Boston to Annapolis. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Boston to Annapolis as you normally would.

What is the cheapest day to fly from Boston to Annapolis?

Use this chart to determine the cheapest time to fly round-trip from Boston to Annapolis. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Boston to Annapolis flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Boston to Annapolis

Explore weekly flight availability from Boston to Annapolis. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated septiembre 16, 2025.

The most flights from BOS to AP9 are scheduled on a Tuesday (22 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

How much does it cost to fly round-trip from Boston to Annapolis?

Reviews of airlines servicing Annapolis

Get insights into the airlines that provide service to Annapolis. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Annapolis. Reviews last updated septiembre 16, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Boston to Annapolis to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,957 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,924 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.2
Good
2,914 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,019 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Boston to Annapolis. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Boston to Annapolis?

    For a flight from Boston to Annapolis, you will be flying from Logan Intl. Boston Logan Intl (BOS) is just 2.6 mi from the center of the city. Logan Intl is the only Boston airport and it handles 71 outbound flights to Annapolis per day. 6 airlines have flights to Annapolis from Boston Logan Intl on a regular basis.

  • How long is the flight from Boston to Annapolis?

    There are many flights that can get you from Boston to Annapolis in 1h 35m. Fly via United Airlines, Delta, or Southwest to get the fastest option. The distance between Boston and Annapolis is about 369 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Boston to Annapolis?

    The most popular route from Boston to Annapolis is Boston Logan Intl - Baltimore/Washington. You may also consider Boston Logan Intl - Washington, D.C. Reagan-National or Boston Logan Intl - Washington, D.C. Dulles Intl.

  • What are the most reliable airlines from Boston to Annapolis?

    Before booking your flight to Annapolis from Boston, check out the most reliable airlines to get you to your destination on time: Ethiopian Air (97%), Air China (94%), Egyptair( 92%).

  • What are the cheapest flights from Boston to Annapolis?

    On average you can expect to pay $770 for a flight from Boston to Annapolis. The cheapest flight overall is $93 while the most popular route, (Boston Logan Intl - Baltimore/Washington) is currently priced at $131.

  • Can I find deals for flights from Boston to Annapolis that include hotel bookings?

    Yes. In addition to deals on Boston to Annapolis flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Annapolis?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Annapolis.

  • Can I find deals for business class flights from Boston to Annapolis?

    Yes. Cheapflights offers flight deals from Boston to Annapolis by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Boston to Annapolis?

    Currently, August is the cheapest month in which you can book a flight from Boston to Annapolis (average of $292). Flying from Boston to Annapolis in April is currently the most expensive (average of $337). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Boston to Annapolis

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Baltimore flights
Boston to Reagan-National flights
Boston to Dulles Intl flights
Boston to Philadelphia flights
Hartford to Reagan-National flights
Hartford to Dulles Intl flights
Hartford to Baltimore flights
Albany to Reagan-National flights
Albany to Dulles Intl flights
Hartford to Philadelphia flights
Albany to Baltimore flights
Albany to Philadelphia flights
Hyannis to Reagan-National flights
Worcester to Philadelphia flights
Hyannis to Philadelphia flights
Worcester to Dulles Intl flights
Nantucket to Reagan-National flights
Boston to Salisbury flights
West Tisbury to Reagan-National flights
Hartford to Salisbury flights
West Tisbury to Philadelphia flights
Nantucket to Philadelphia flights
Provincetown to Reagan-National flights
Hyannis to Dulles Intl flights
Nantucket to Dulles Intl flights
Provincetown to Philadelphia flights
Hyannis to Baltimore flights
West Tisbury to Dulles Intl flights
Nantucket to Baltimore flights
West Tisbury to Baltimore flights

Top 6 airlines flying from Boston to Annapolis

Discover the top 6 airlines that operate flights from Boston to Annapolis. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$49Average$135FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$68Average$252FlexibilityNo cancel feeOn-time62%
DeltaCheapest$84Average$247FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$137Average$273FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$147Average$254FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$164Average$273FlexibilityNo cancel feeOn-time63%

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