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Cheap flights from Boston (BOS) to Annapolis, MD

BOS — IAD
Nov 29 — Dec 61
Sun 11/29
Sun 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Annapolis are usually found in December or January, booked 46 days in advance, depart on a Friday or Thursday and return on a Friday

Find flight deals from Boston to Annapolis

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

June

Cheapest in

December

Average price

$309
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.
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Highest demand for flights based on searches. 9% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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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?

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 13% versus a flight at noon.

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

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

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
4,217 reviews

Food

7.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.4

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Edward,Sep 2026

MCO - BWI

Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.
Southwest
7.9
Good
4,217 reviews
Southwest
7.9
Good
4,217 reviews

Food

7.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.4

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Edward,Sep 2026

MCO - BWI

Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.
Delta
7.8
Good
8,691 reviews
Southwest
7.9
Good
4,217 reviews

Food

7.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.4

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Edward,Sep 2026

MCO - BWI

Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.
United Airlines
7.3
Good
10,454 reviews
Southwest
7.9
Good
4,217 reviews

Food

7.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.4

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Edward,Sep 2026

MCO - BWI

Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.
JetBlue
7.1
Good
3,076 reviews
Southwest
7.9
Good
4,217 reviews

Food

7.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.4

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Edward,Sep 2026

MCO - BWI

Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.
American Airlines
7.0
Good
12,209 reviews
Southwest
7.9
Good
4,217 reviews

Food

7.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.4

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Edward,Sep 2026

MCO - BWI

Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.

Related info for your journey

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

  • 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 $68 on JetBlue. Other airlines that offer cheap prices include American Airlines from $76 and Delta from $80 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 (95%), Egyptair (92%), Air China( 88%).

  • What are the cheapest flights from Boston to Annapolis?

    On average you can expect to pay $902 for a flight from Boston to Annapolis. The cheapest flight overall is $126 while the most popular route, (Boston Logan Intl - Washington, D.C. Reagan-National) is currently priced at $104.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Top 6 airlines flying from Boston to Annapolis

AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$117Average$269FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$117Average$264FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$148Average$286FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$160Average$300FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$166Average$328FlexibilityNo cancel feeOn-time63%
FrontierCheapest$218Average$302FlexibilityNo cancel feeOn-time62%

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