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$91+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — IAD
Jul 14 — Jul 211
Tue 7/14
Tue 7/21
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Annapolis are usually found in September or December, booked 37 days in advance, depart on a Friday or Saturday 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 June 14, 2026.

This American Airlines deal was found by Cheapflights users on 6/11. 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.
Tue 7/218:19 am
BOS
-
DCA
Nonstop1h 42m
American Airlines
Thu 8/68:13 am
DCA
-
BOS
Nonstop1h 40m
American Airlines
Deal found 6/11$176
This Delta deal was found by Cheapflights users on 6/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:35 pm
BOS
-
BWI
Nonstop1h 54m
Delta
Sun 7/266:21 am
BWI
-
BOS
Nonstop1h 39m
Delta
Deal found 6/13$176
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Mon 9/287:00 pm
BOS
-
IAD
1 stop3h 59m
United Airlines
Wed 9/306:45 am
IAD
-
BOS
1 stop4h 39m
United Airlines
Deal found 6/10$177
This United Airlines deal was found by Cheapflights users on 6/9. 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 7/89:30 am
BOS
-
DCA
1 stop4h 53m
United Airlines
Tue 7/1411:00 am
DCA
-
BOS
1 stop5h 38m
United Airlines
Deal found 6/9$177
This United Airlines deal was found by Cheapflights users on 6/12. 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 7/19:25 am
BOS
-
IAD
Nonstop1h 42m
United Airlines
Tue 7/73:30 pm
IAD
-
BOS
Nonstop1h 54m
United Airlines
Deal found 6/12$178
This Priceline deal was found by Cheapflights users on 6/12. 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.
Thu 7/21:05 pm
BOS
-
DCA
Nonstop1h 40m
JetBlue
Tue 7/71:25 pm
DCA
-
BOS
Nonstop1h 34m
JetBlue
Deal found 6/12$178
This United Airlines deal was found by Cheapflights users on 6/12. 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 7/155:45 am
BOS
-
IAD
Nonstop1h 38m
United Airlines
Tue 7/2110:10 pm
IAD
-
BOS
Nonstop1h 49m
United Airlines
Deal found 6/12$179
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:05 am
BOS
-
DCA
Nonstop1h 44m
JetBlue
Wed 8/55:59 pm
DCA
-
BOS
Nonstop1h 41m
JetBlue
Deal found 6/10$179
This Southwest deal was found by Cheapflights users on 6/11. 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.
Tue 9/84:55 pm
BOS
-
BWI
Nonstop1h 45m
Southwest
Fri 9/118:40 pm
BWI
-
BOS
Nonstop1h 30m
Southwest
Deal found 6/11$179
This United Airlines deal was found by Cheapflights users on 6/11. 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 8/195:45 am
BOS
-
IAD
Nonstop1h 35m
United Airlines
Fri 8/288:35 am
IAD
-
BOS
1 stop5h 47m
United Airlines
Deal found 6/11$180
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:15 am
BOS
-
DCA
Nonstop1h 43m
JetBlue
Mon 8/106:25 pm
DCA
-
BOS
Nonstop1h 34m
JetBlue
Deal found 6/11$180
This United Airlines deal was found by Cheapflights users on 6/10. 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 8/65:45 am
BOS
-
IAD
Nonstop1h 38m
United Airlines
Thu 8/138:35 am
IAD
-
BOS
1 stop4h 12m
United Airlines
Deal found 6/10$181

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 June 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$176
(United Airlines)

One-way from

$91
(United Airlines)

Popular in

May

Cheapest in

September

Average price

$268
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. 9% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 14, 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

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

Sun 8/23

6:05 am-10:09 am

1 stop4h 04m

Washington, D.C. Reagan-National

Wed 8/26

6:35 pm-8:34 pm

Nonstop1h 59m

$182

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

Sun 7/12

6:05 am-10:09 am

1 stop4h 04m

Washington, D.C. Reagan-National

Tue 7/21

10:05 am-11:48 am

Nonstop1h 43m

$182

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

Sun 8/2

5:45 am-7:23 am

Nonstop1h 38m

Washington, D.C. Dulles Intl

Wed 8/5

10:10 pm-11:59 pm

Nonstop1h 49m

$184

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

Fri 9/4

9:30 am-11:11 am

Nonstop1h 41m

Washington, D.C. Dulles Intl

Mon 9/7

10:15 pm-11:59 pm

Nonstop1h 44m

$185

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

Tue 7/14

9:25 am-11:07 am

Nonstop1h 42m

Washington, D.C. Dulles Intl

Sun 7/19

10:10 pm-11:59 pm

Nonstop1h 49m

$192

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

Fri 7/10

5:45 am-7:23 am

Nonstop1h 38m

Washington, D.C. Dulles Intl

Wed 7/15

10:10 pm-11:59 pm

Nonstop1h 49m

$192

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

Tue 9/8

5:45 am-7:20 am

Nonstop1h 35m

Washington, D.C. Dulles Intl

Fri 9/11

6:15 am-9:48 am

1 stop3h 33m

$194

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

Sun 8/2

6:05 am-7:49 am

Nonstop1h 44m

Washington, D.C. Reagan-National

Thu 8/6

9:00 am-10:35 am

Nonstop1h 35m

$199
Quickest round-trip

BostonBaltimore

BOS - BWI

BOSBWI

Boston Logan Intl

Fri 9/4

5:50 am-7:15 am

Nonstop1h 25m

Baltimore/Washington

Mon 9/7

6:30 am-8:00 am

Nonstop1h 30m

$200

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

Sat 7/4

9:25 am-11:07 am

Nonstop1h 42m

Washington, D.C. Dulles Intl

Tue 7/7

5:42 pm-9:55 pm

1 stop4h 13m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 June 14, 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 50% versus a flight in the afternoon.

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 June 14, 2026.

The most flights from BOS to AP9 are scheduled on a Tuesday (20 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (17 on average).

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

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 June 13, 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. Sunday 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 June 14, 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
7.9
Good
4,234 reviews

Overall

7.9

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
Southwest
7.9
Good
4,234 reviews
Southwest
7.9
Good
4,234 reviews

Overall

7.9

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
Delta
7.9
Good
8,403 reviews
Southwest
7.9
Good
4,234 reviews

Overall

7.9

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
United Airlines
7.4
Good
9,819 reviews
Southwest
7.9
Good
4,234 reviews

Overall

7.9

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
American Airlines
7.1
Good
11,654 reviews
Southwest
7.9
Good
4,234 reviews

Overall

7.9

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
JetBlue
7.1
Good
2,981 reviews
Southwest
7.9
Good
4,234 reviews

Overall

7.9

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

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 53 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 38m. Fly via Delta, United Airlines, or JetBlue to get the fastest option. The distance between Boston and Annapolis is about 411 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 $73 on JetBlue. Other airlines that offer cheap prices include United Airlines from $78 and American Airlines from $81 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: Ethiopian Air (98%), Egyptair (96%), Air China( 94%).

  • What are the cheapest flights from Boston to Annapolis?

    On average you can expect to pay $843 for a flight from Boston to Annapolis. The cheapest flight overall is $118 while the most popular route, (Boston Logan Intl - Washington, D.C. Reagan-National) is currently priced at $108.

  • 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 June 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$84Average$263FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$118Average$241FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$127Average$252FlexibilityNo cancel feeOn-time62%
FrontierCheapest$138Average$250FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$154Average$262FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$169Average$309FlexibilityNo cancel feeOn-time63%

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