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$49+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — BWI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Annapolis are usually found in January or August, booked 89 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 junio 12, 2025.

Round-trip from

$83
(FlightHub)

One-way from

$49
(FlightHub)

Popular in

November

Cheapest in

January

Average price

$209
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. 6% potential increase in price ($12 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 June 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 junio 12, 2025.

This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/256:00 amBOS - BWI
Nonstop1h 30mSpirit Airlines
jue. 6/265:45 amBWI - BOS
Nonstop1h 27mSpirit Airlines
Deal found 6/11$83
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/116:00 amBOS - DCA
Nonstop1h 38mJetBlue
lun. 8/1110:30 amDCA - BOS
Nonstop1h 35mJetBlue
Deal found 6/11$156
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.
mié. 8/139:30 amBOS - IAD
Nonstop1h 40mUnited Airlines
lun. 8/185:10 pmIAD - BOS
Nonstop1h 46mUnited Airlines
Deal found 6/10$161
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/76:05 amBOS - DCA
Nonstop1h 55mDelta
lun. 8/118:40 amDCA - BOS
Nonstop1h 48mDelta
Deal found 6/10$161
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/318:30 amBOS - DCA
Nonstop1h 44mAmerican Airlines
lun. 8/47:00 amDCA - BOS
Nonstop1h 48mAmerican Airlines
Deal found 6/10$165
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.
vie. 7/45:20 amBOS - BWI
Nonstop1h 30mSouthwest
vie. 7/47:00 pmBWI - BOS
Nonstop1h 35mSouthwest
Deal found 6/11$173
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/1210:45 amBOS - BWI
Nonstop1h 43mDelta
lun. 7/149:00 amBWI - BOS
Nonstop1h 34mDelta
Deal found 6/11$174
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/2411:31 amBOS - IAD
1 stop8h 49mAllegiant Air
lun. 7/283:13 pmIAD - BOS
1 stop18h 02mAllegiant Air
Deal found 6/11$175
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/1011:31 amBOS - IAD
1 stop8h 49mMultiple Airlines
jue. 8/1411:04 amIAD - BOS
1 stop23h 35mMultiple Airlines
Deal found 6/11$179
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.
jue. 8/78:47 amBOS - DCA
1 stop5h 35mUnited Airlines
lun. 8/117:01 pmDCA - BOS
1 stop4h 09mUnited Airlines
Deal found 6/10$181
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/206:00 amBOS - BWI
1 stop17h 14mMultiple Airlines
mar. 6/242:15 pmBWI - BOS
Nonstop1h 30mMultiple Airlines
Deal found 6/10$181
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/252:49 pmBOS - BWI
1 stop7h 26mAmerican Airlines
lun. 7/285:00 amBWI - BOS
1 stop4h 50mAmerican Airlines
Deal found 6/12$193

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 junio 12, 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

BostonBaltimore

BOS - BWI

BOSBWI

Boston Logan Intl

mié. 6/25

6:00 am-7:30 am

Nonstop1h 30m

Baltimore/Washington

jue. 6/26

5:45 am-7:12 am

Nonstop1h 27m

$83

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

lun. 8/11

6:00 am-7:38 am

Nonstop1h 38m

Washington, D.C. Reagan-National

lun. 8/11

10:30 am-12:05 pm

Nonstop1h 35m

$156

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

mié. 8/13

9:30 am-11:10 am

Nonstop1h 40m

Washington, D.C. Dulles Intl

lun. 8/18

5:10 pm-6:56 pm

Nonstop1h 46m

$161

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

jue. 8/7

6:05 am-8:00 am

Nonstop1h 55m

Washington, D.C. Reagan-National

lun. 8/11

8:40 am-10:28 am

Nonstop1h 48m

$161

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

jue. 7/31

8:30 am-10:14 am

Nonstop1h 44m

Washington, D.C. Reagan-National

lun. 8/4

7:00 am-8:48 am

Nonstop1h 48m

$165

BostonBaltimore

BOS - BWI

BOSBWI

Boston Logan Intl

vie. 7/4

11:40 am-1:23 pm

Nonstop1h 43m

Baltimore/Washington

vie. 7/11

9:00 am-10:34 am

Nonstop1h 34m

$173

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

jue. 7/24

11:31 am-8:20 pm

1 stop8h 49m

Washington, D.C. Dulles Intl

lun. 7/28

3:13 pm-9:15 am

1 stop18h 02m

$175

BostonWashington, D.C.

BOS - IAD

BOSIAD

Boston Logan Intl

dom. 8/10

11:31 am-8:20 pm

1 stop8h 49m

Washington, D.C. Dulles Intl

jue. 8/14

11:04 am-10:39 am

1 stop23h 35m

$179

BostonWashington, D.C.

BOS - DCA

BOSDCA

Boston Logan Intl

jue. 8/7

8:47 am-2:22 pm

1 stop5h 35m

Washington, D.C. Reagan-National

lun. 8/11

7:01 pm-11:10 pm

1 stop4h 09m

$181

BostonBaltimore

BOS - BWI

BOSBWI

Boston Logan Intl

jue. 7/17

1:30 pm-3:10 pm

Nonstop1h 40m

Baltimore/Washington

jue. 7/17

10:50 pm-12:25 am

Nonstop1h 35m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 35 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 June 9, 2025.

To ensure you get the cheapest price possible for a flight from Boston to Annapolis, you should look to book at least 89 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 $241). Flying from Boston to Annapolis in March is currently the most expensive (average of $290). 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 junio 12, 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 June 8, 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. Saturday 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 junio 12, 2025.

The most flights from BOS to AP9 are scheduled on a Thursday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Annapolis by month

Plan your trip to Annapolis by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Annapolis ranges from 2.6 - 4.0 inches per month. May is typically the wettest month, when rainfall can reach 4.0 in. February is typically the driest time to visit Annapolis when rainfall is around 2.6 in.

Temperature in Annapolis by month

Plan your trip to Annapolis by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Annapolis, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 35.6 F).

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 junio 12, 2025.
See what other customers who have flown with Southwest, Delta and United Airlines from Boston to Annapolis have to say. 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
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,925 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 58 outbound flights to Annapolis per day. 6 airlines have flights to Annapolis from Boston Logan Intl on a regular basis.

  • How popular is this Boston to Annapolis flight route?

    The Boston Logan Intl to Annapolis flight path was viewed by 251 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • 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 $49 on Spirit Airlines. Other airlines that offer cheap prices include United Airlines from $81 and Delta 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: Virgin Atlantic (94%), Korean Air (84%), KLM( 79%).

  • What are the cheapest flights from Boston to Annapolis?

    On average you can expect to pay $249 for a flight from Boston to Annapolis. The cheapest flight overall is $51 while the most popular route, (Boston Logan Intl - Washington, D.C. Reagan-National) is currently priced at $156.

  • 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 $241). Flying from Boston to Annapolis in March is currently the most expensive (average of $290). 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 Philadelphia flights
Boston to Dulles Intl flights
Hartford to Dulles Intl flights
Hartford to Baltimore flights
Hartford to Reagan-National flights
Albany to Reagan-National flights
Albany to Dulles Intl flights
Albany to Baltimore flights
Hartford to Philadelphia flights
Albany to Philadelphia flights
West Tisbury to Reagan-National flights
Hyannis to Reagan-National flights
Nantucket to Reagan-National flights
Boston to Salisbury flights
Worcester to Philadelphia flights
Hyannis to Philadelphia flights
West Tisbury to Philadelphia flights
Hyannis to Baltimore flights
Hartford to Salisbury flights
West Tisbury to Dulles Intl flights
Worcester to Dulles Intl flights
Hyannis to Dulles Intl flights
Nantucket to Philadelphia flights
Nantucket to Dulles Intl flights
West Tisbury to Baltimore flights
Provincetown to Reagan-National flights
Nantucket to Baltimore flights
Provincetown to Philadelphia 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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$49Average$105FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$60Average$246FlexibilityNo cancel feeOn-time62%
DeltaCheapest$110Average$244FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$139Average$243FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$258FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$175Average$272FlexibilityNo cancel feeOn-time63%

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