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Cheap flights from Cleveland (CLE) to Annapolis, MD

CLE — IAD
Dec 3 — Dec 101
Thu 12/3
Thu 12/10
1 adult, Economy
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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Annapolis are usually found in December or April, booked 59 days in advance, depart on a Friday or Thursday and return on a Saturday

Find flight deals from Cleveland to Annapolis

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

October

Cheapest in

December

Average price

$279
Provider with most accurate pricing for Cleveland Hopkins Intl-Washington, D.C. (WAS) flight deals.
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Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-Washington, D.C. (WAS) flights.
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Highest demand for flights based on searches. 7% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in November 2026
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Cheapflights Insights

Everything you need to know about your flight from Cleveland to Annapolis

What is the cheapest time of day to fly from CLE to AP9?

It’s optimal to fly from Cleveland to Annapolis in the morning. By choosing this option you can save up to 33% on the cost of your flight, compared to a flight in the evening.

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

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

Reviews of airlines servicing Annapolis

Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Cleveland to Annapolis by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,220 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
8.0
Very good
4,220 reviews
Southwest
8.0
Very good
4,220 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
10,463 reviews
Southwest
8.0
Very good
4,220 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
12,222 reviews
Southwest
8.0
Very good
4,220 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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.
Frontier
5.5
Fair
2,511 reviews
Southwest
8.0
Very good
4,220 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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 Cleveland to Annapolis?

    Cleveland Hopkins Intl (CLE), located 10.1 mi from the city center, is the airport you fly out of when you book flights from Cleveland to Annapolis. 5 airlines have flights from Hopkins Intl to Annapolis on a regular basis. Booking flights from Cleveland Hopkins Intl to Annapolis should not be difficult; the airport handles an average of 14 outbound flights to Annapolis per day.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $105. However, be on the lookout for offers from JetBlue and American Airlines, as they are both options that can get you from Cleveland to Annapolis for a low price.

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

    The most popular flight routes from Cleveland to Annapolis are Cleveland Hopkins Intl - Washington, D.C. Dulles Intl, Cleveland Hopkins Intl - Washington, D.C. Reagan-National and Cleveland Hopkins Intl - Baltimore/Washington.

  • What are the most reliable airlines from Cleveland to Annapolis?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Cleveland to Annapolis on time: GoJet (100%), ANA (100%), Ethiopian Air (100%).

  • What are the cheapest flights from Cleveland to Annapolis?

    Looking for the cheapest flight from Cleveland to Annapolis? While on average our users pay $657, our data indicates the cheapest price to be $202. The most popular route (Cleveland Hopkins Intl - Washington, D.C. Dulles Intl), is priced around $157.

  • Can I find deals for flights from Cleveland to Annapolis that include hotel bookings?

    Yes. In addition to deals on Cleveland to Annapolis flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Cleveland to Annapolis?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cleveland to Annapolis.

  • Can I find deals for business class flights from Cleveland to Annapolis?

    Yes. Cheapflights offers flight deals from Cleveland 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 5 airlines flying from Cleveland to Annapolis

AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$117Average$320FlexibilityNo cancel feeOn-time63%
FrontierCheapest$131Average$235FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$137Average$415FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$344FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$245Average$364FlexibilityNo cancel feeOn-time62%

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