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$74+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — IAD
Aug 29 — Sep 51
Sat 8/29
Sat 9/5
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Annapolis are usually found in December or September, booked 37 days in advance, depart on a Friday or Wednesday and return on a Friday

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 July 30, 2026.

This Delta deal was found by Cheapflights users on 7/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:45 pm
BOS
-
BWI
Nonstop1h 46m
Delta
Fri 9/116:17 am
BWI
-
BOS
Nonstop1h 43m
Delta
Deal found 7/25$157
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 9/253:45 pm
BOS
-
BWI
Nonstop1h 42m
Delta
Mon 9/286:19 pm
BWI
-
BOS
Nonstop1h 41m
Delta
Deal found 7/29$158
This United Airlines deal was found by Cheapflights users on 7/29. 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 8/205:45 am
BOS
-
IAD
Nonstop1h 35m
United Airlines
Mon 8/248:35 am
IAD
-
BOS
Nonstop1h 43m
United Airlines
Deal found 7/29$161
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Fri 9/45:45 am
BOS
-
IAD
Nonstop1h 35m
United Airlines
Sun 9/610:15 pm
IAD
-
BOS
Nonstop1h 44m
United Airlines
Deal found 7/29$162
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Tue 10/205:45 am
BOS
-
IAD
Nonstop1h 35m
United Airlines
Fri 10/308:37 am
IAD
-
BOS
1 stop3h 49m
United Airlines
Deal found 7/29$163
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:50 am
BOS
-
BWI
Nonstop1h 25m
Southwest
Fri 9/186:30 am
BWI
-
BOS
Nonstop1h 30m
Southwest
Deal found 7/27$163
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Sun 9/205:45 am
BOS
-
IAD
Nonstop1h 35m
United Airlines
Wed 9/235:28 pm
IAD
-
BOS
Nonstop1h 51m
United Airlines
Deal found 7/29$164
This American Airlines deal was found by Cheapflights users on 7/28. 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.
Fri 9/116:00 am
BOS
-
DCA
Nonstop1h 47m
American Airlines
Fri 9/1810:16 pm
DCA
-
BOS
Nonstop1h 38m
American Airlines
Deal found 7/28$164
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Fri 9/47:23 pm
BOS
-
IAD
Nonstop1h 45m
United Airlines
Mon 9/710:15 pm
IAD
-
BOS
Nonstop1h 44m
United Airlines
Deal found 7/29$166
This Super.com deal was found by Cheapflights users on 7/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:08 pm
BOS
-
DCA
1 stop3h 51m
JetBlue
Mon 8/242:25 pm
DCA
-
BOS
Nonstop1h 35m
JetBlue
Deal found 7/29$166
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Fri 9/117:00 pm
BOS
-
IAD
1 stop3h 59m
United Airlines
Sun 9/1310:15 pm
IAD
-
BOS
Nonstop1h 44m
United Airlines
Deal found 7/28$167
This Delta deal was found by Cheapflights users on 7/28. 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.
Sun 9/137:30 am
BOS
-
DCA
Nonstop2h 00m
Delta
Tue 9/156:59 am
DCA
-
BOS
Nonstop1h 41m
Delta
Deal found 7/28$167

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 July 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$157
(Delta)

One-way from

$74
(Frontier)

Popular in

June

Cheapest in

December

Average price

$279
Provider with most accurate pricing for Boston Logan Intl-Washington, D.C. (WAS) flight deals.
Search Deals
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. 12% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 July 30, 2026.
Use the filters below to find and compare flights from Boston to Annapolis that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonBaltimore

BOS - BWI

BOSBWI

Boston Logan Intl

Fri 8/21

8:55 pm-10:35 pm

Nonstop1h 40m

Baltimore/Washington

Mon 8/24

6:30 am-8:00 am

Nonstop1h 30m

$158

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

Thu 10/22

10:51 am-4:23 pm

1 stop5h 32m

Washington, D.C. Dulles Intl

Mon 10/26

10:19 pm-11:59 pm

Nonstop1h 40m

$180
Quickest round-trip

BostonBaltimore

BOS - BWI

BOSBWI

Boston Logan Intl

Fri 10/9

9:45 pm-11:15 pm

Nonstop1h 30m

Baltimore/Washington

Tue 10/13

8:20 am-9:55 am

Nonstop1h 35m

$181

BostonBaltimore

BOS - BWI

BOSBWI

Boston Logan Intl

Wed 9/2

5:30 am-11:32 am

1 stop6h 02m

Baltimore/Washington

Thu 9/3

9:00 am-10:38 am

Nonstop1h 38m

$182

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

Tue 10/20

5:45 am-7:20 am

Nonstop1h 35m

Washington, D.C. Dulles Intl

Tue 10/27

12:50 pm-2:32 pm

Nonstop1h 42m

$187

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

Tue 10/20

2:30 pm-4:19 pm

Nonstop1h 49m

Washington, D.C. Reagan-National

Fri 10/23

6:10 am-9:19 am

1 stop3h 09m

$187

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

Tue 8/18

5:45 am-7:20 am

Nonstop1h 35m

Washington, D.C. Dulles Intl

Tue 8/25

10:15 pm-11:59 pm

Nonstop1h 44m

$187

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

Thu 8/20

6:05 am-10:09 am

1 stop4h 04m

Washington, D.C. Reagan-National

Mon 8/24

10:00 pm-11:42 pm

Nonstop1h 42m

$187

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

Thu 10/15

9:40 am-11:31 am

Nonstop1h 51m

Washington, D.C. Reagan-National

Sat 10/17

1:25 pm-7:22 pm

1 stop5h 57m

$187

BostonBaltimore

BOS - BWI

BOSBWI

Boston Logan Intl

Tue 10/20

5:39 am-11:52 am

1 stop6h 13m

Baltimore/Washington

Thu 10/22

6:03 am-7:40 am

Nonstop1h 37m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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

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 July 30, 2026.

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 morning, which can drop the price by up to 12% versus a flight at noon.

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 July 30, 2026.

The most flights from BOS to AP9 are scheduled on a Thursday (22 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (16 on average).

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

Airfare is below average for this route at the moment.
Boston to Annapolis flights typically cost between $185 and $349 in September.
The cheapest round-trip price found within the last 5 days was $157 on Delta (Sep 10-Sep 11).

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 July 25, 2026.

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

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 July 30, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited 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.
Southwest
8.0
Very good
4,227 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Joseph,Sep 2023

LAX - BWI

The plane departure and arrival were on time. The crew was entertaining and professional at the same time. Baggage claim was efficient. Glad I flew on Southwest airlines.
Southwest
8.0
Very good
4,227 reviews
Southwest
8.0
Very good
4,227 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Joseph,Sep 2023

LAX - BWI

The plane departure and arrival were on time. The crew was entertaining and professional at the same time. Baggage claim was efficient. Glad I flew on Southwest airlines.
Delta
7.8
Good
8,486 reviews
Southwest
8.0
Very good
4,227 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Joseph,Sep 2023

LAX - BWI

The plane departure and arrival were on time. The crew was entertaining and professional at the same time. Baggage claim was efficient. Glad I flew on Southwest airlines.
United Airlines
7.4
Good
10,052 reviews
Southwest
8.0
Very good
4,227 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Joseph,Sep 2023

LAX - BWI

The plane departure and arrival were on time. The crew was entertaining and professional at the same time. Baggage claim was efficient. Glad I flew on Southwest airlines.
American Airlines
7.1
Good
11,839 reviews
Southwest
8.0
Very good
4,227 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Joseph,Sep 2023

LAX - BWI

The plane departure and arrival were on time. The crew was entertaining and professional at the same time. Baggage claim was efficient. Glad I flew on Southwest airlines.
JetBlue
7.1
Good
3,024 reviews
Southwest
8.0
Very good
4,227 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Joseph,Sep 2023

LAX - BWI

The plane departure and arrival were on time. The crew was entertaining and professional at the same time. Baggage claim was efficient. Glad I flew on Southwest airlines.

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 60 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 40m. Fly via Southwest, United Airlines, or Delta 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 cheapest airlines to fly from Boston to Annapolis one-way?

    One-way options have recently been found by users for as low as $74 on JetBlue. Other airlines that offer cheap prices include United Airlines from $78 and Delta from $83 one-way.

  • 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: Egyptair (100%), Air China (100%), Ethiopian Air( 97%).

  • What are the cheapest flights from Boston to Annapolis?

    On average you can expect to pay $1,223 for a flight from Boston to Annapolis. The cheapest flight overall is $128 while the most popular route, (Boston Logan Intl - Baltimore/Washington) is currently priced at $117.

  • 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.

See more FAQs

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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 July 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$84Average$266FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$118Average$236FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$127Average$254FlexibilityNo cancel feeOn-time62%
FrontierCheapest$140Average$301FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$155Average$268FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$176Average$320FlexibilityNo cancel feeOn-time63%

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