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$75+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — IAD
Jan 24 — Jan 311
Sat 1/24
Sat 1/31
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Annapolis are usually found in January or February, booked 74 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap 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 December 25, 2025.

This United Airlines deal was found by Cheapflights users on 12/23. 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.
Thu 12/257:32 pmBOS - IAD
1 stop3h 34mUnited Airlines
Sat 1/2412:40 pmIAD - BOS
Nonstop1h 37mUnited Airlines
Deal found 12/23$187
This United Airlines deal was found by Cheapflights users on 12/23. 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.
Thu 12/257:32 pmBOS - IAD
1 stop3h 34mUnited Airlines
Thu 1/85:20 pmIAD - BOS
Nonstop1h 37mUnited Airlines
Deal found 12/23$202
This United Airlines deal was found by Cheapflights users on 12/23. 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.
Wed 12/242:15 pmBOS - IAD
Nonstop1h 46mUnited Airlines
Thu 12/255:10 pmIAD - BOS
Nonstop1h 38mUnited Airlines
Deal found 12/23$207
This JetBlue deal was found by Cheapflights users on 12/22. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:00 pmBOS - DCA
Nonstop1h 50mJetBlue
Wed 1/78:55 pmDCA - BOS
Nonstop1h 35mJetBlue
Deal found 12/22$217
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
Wed 12/316:00 amBOS - IAD
1 stop29h 38mFrontier
Wed 1/75:42 pmIAD - BOS
1 stop7h 37mFrontier
Deal found 12/22$219
This JetBlue deal was found by Cheapflights users on 12/22. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:00 pmBOS - DCA
Nonstop1h 50mJetBlue
Mon 1/58:51 pmDCA - BOS
Nonstop1h 35mJetBlue
Deal found 12/22$222
This United Airlines deal was found by Cheapflights users on 12/22. 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.
Wed 12/244:28 pmBOS - IAD
1 stop4h 26mUnited Airlines
Thu 1/15:10 pmIAD - BOS
1 stop5h 38mUnited Airlines
Deal found 12/22$227
This Delta deal was found by Cheapflights users on 12/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:00 amBOS - DCA
1 stop6h 11mDelta
Wed 1/710:05 pmDCA - BOS
Nonstop1h 36mDelta
Deal found 12/22$227
This United Airlines deal was found by Cheapflights users on 12/24. 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.
Wed 12/317:44 pmBOS - IAD
Nonstop1h 46mUnited Airlines
Sat 1/310:17 pmIAD - BOS
Nonstop1h 37mUnited Airlines
Deal found 12/24$232
This Delta deal was found by Cheapflights users on 12/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:00 amBOS - DCA
1 stop6h 11mDelta
Tue 1/66:59 amDCA - BOS
Nonstop1h 41mDelta
Deal found 12/22$232
This United Airlines deal was found by Cheapflights users on 12/25. 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.
Thu 12/257:44 pmBOS - IAD
Nonstop1h 46mUnited Airlines
Thu 1/19:00 amIAD - BOS
Nonstop1h 37mUnited Airlines
Deal found 12/25$237
This Kiwi.com deal was found by Cheapflights users on 12/24. 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.
Wed 12/316:00 amBOS - BWI
1 stop18h 29mFrontier
Wed 1/78:00 amBWI - BOS
1 stop26h 11mFrontier
Deal found 12/24$239

Find flight deals from Boston to Annapolis

Keep the following information in mind while searching for Boston to Annapolis flight deals. Data was last updated December 25, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$146
(Kiwi.com)

One-way from

$75
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$207
Provider with most accurate pricing for Boston Logan Intl-Washington, D.C. (WAS) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Washington, D.C. (WAS) flights.
Search Deals
From Boston Logan Intl to Annapolis
Search Deals
One-way flight from Boston Logan Intl to Annapolis
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 25, 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 - IAD

BOSIAD

Boston Logan Intl

Wed 1/28

7:07 pm-8:53 pm

Nonstop1h 46m

Washington, D.C. Dulles Intl

Sat 1/31

5:20 pm-6:57 pm

Nonstop1h 37m

$147

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

Tue 1/20

9:30 am-11:16 am

Nonstop1h 46m

Washington, D.C. Dulles Intl

Tue 1/20

5:20 pm-6:57 pm

Nonstop1h 37m

$147

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

Sat 1/31

11:55 am-1:53 pm

Nonstop1h 58m

Washington, D.C. Reagan-National

Sun 2/1

7:00 am-8:39 am

Nonstop1h 39m

$157

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

Sat 1/31

12:40 pm-2:29 pm

Nonstop1h 49m

Washington, D.C. Reagan-National

Sun 2/1

8:55 pm-10:30 pm

Nonstop1h 35m

$157

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

Sat 1/17

2:15 pm-4:12 pm

Nonstop1h 57m

Washington, D.C. Reagan-National

Sun 1/18

10:05 pm-11:41 pm

Nonstop1h 36m

$157

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

Sat 1/17

7:55 pm-9:45 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Sun 1/18

7:00 am-8:32 am

Nonstop1h 32m

$157

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

Sat 1/24

2:10 pm-4:07 pm

Nonstop1h 57m

Washington, D.C. Reagan-National

Sun 1/25

10:25 am-12:06 pm

Nonstop1h 41m

$157

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

Mon 1/19

11:30 am-1:20 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Wed 1/21

8:55 pm-10:30 pm

Nonstop1h 35m

$157

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

Sun 1/11

9:30 am-11:16 am

Nonstop1h 46m

Washington, D.C. Dulles Intl

Wed 1/14

10:12 pm-11:49 pm

Nonstop1h 37m

$162

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

Wed 1/14

9:30 am-11:16 am

Nonstop1h 46m

Washington, D.C. Dulles Intl

Thu 1/15

8:29 am-1:13 pm

1 stop4h 44m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 60 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 December 19, 2025.

To ensure you get the cheapest price possible for a flight from Boston to Annapolis, you should look to book at least 74 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, January is the cheapest month in which you can book a flight from Boston to Annapolis (average of $38). Flying from Boston to Annapolis in October is currently the most expensive (average of $137). 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 December 25, 2025.

When flying from Boston to Annapolis, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 45% versus a flight in the afternoon.

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 December 20, 2025.

Travelers seeking maximum savings on their Boston to Annapolis flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon 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 December 25, 2025.

The most flights from BOS to AP9 are scheduled on a Thursday (18 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (7 on average).

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 December 25, 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
7.9
Good
8,012 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,012 reviews
Delta
7.9
Good
8,012 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,115 reviews
Delta
7.9
Good
8,012 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,061 reviews
Delta
7.9
Good
8,012 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,900 reviews
Delta
7.9
Good
8,012 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,204 reviews
Delta
7.9
Good
8,012 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 31 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 46m. Fly via United Airlines, Delta, or JetBlue to get the fastest option. The distance between Boston and Annapolis is about 411 mi. Most flights are nonstop.

  • What are the cheapest airlines to fly from Boston to Annapolis one-way?

    One-way options have recently been found by users for as low as $29 on Spirit Airlines. Other airlines that offer cheap prices include JetBlue from $68 and Delta from $73 one-way.

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

    The most popular route from Boston to Annapolis is Boston Logan Intl - Washington, D.C. Reagan-National. You may also consider Boston Logan Intl - Baltimore/Washington 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: Air China (100%), Egyptair (96%), ANA( 95%).

  • What are the cheapest flights from Boston to Annapolis?

    On average you can expect to pay $886 for a flight from Boston to Annapolis. The cheapest flight overall is $83 while the most popular route, (Boston Logan Intl - Washington, D.C. Reagan-National) is currently priced at $142.

  • 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, January is the cheapest month in which you can book a flight from Boston to Annapolis (average of $38). Flying from Boston to Annapolis in October is currently the most expensive (average of $137). 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 Reagan-National flights
Boston to Baltimore flights
Boston to Dulles Intl flights
Boston to Philadelphia flights
Hartford to Dulles Intl flights
Hartford to Reagan-National flights
Hartford to Baltimore flights
Albany to Dulles Intl flights
Albany to Reagan-National flights
Albany to Baltimore flights
Hartford to Philadelphia flights
Albany to Philadelphia flights
Hyannis to Reagan-National flights
Nantucket to Reagan-National flights
Worcester to Dulles Intl flights
Worcester to Philadelphia flights
West Tisbury to Philadelphia flights
Hyannis to Philadelphia flights
Boston to Salisbury flights
West Tisbury to Reagan-National flights
Provincetown to Philadelphia flights
Nantucket to Philadelphia flights
Hyannis to Dulles Intl flights
Nantucket to Dulles Intl flights
Hartford to Salisbury flights
West Tisbury to Baltimore flights
Nantucket to Baltimore flights
West Tisbury to Dulles Intl flights
Hyannis to Baltimore flights
Provincetown to Reagan-National 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 December 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$48Average$140FlexibilityNo cancel feeOn-time65%
DeltaCheapest$84Average$255FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$97Average$258FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$122Average$260FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$147Average$252FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$162Average$275FlexibilityNo cancel feeOn-time63%

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