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$53+ Cheap flights from Cleveland (CLE) 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 12/20. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — IAD
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Annapolis are usually found in May or July, booked 57 days in advance, depart on a Friday or Thursday and return on a Wednesday

Cheap flight deals from Cleveland to Annapolis

Keep the following information in mind while searching for Cleveland to Annapolis flight deals. Data was last updated October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$110
(Frontier)

One-way from

$53
(Kiwi.com)

Popular in

March

Cheapest in

May

Average price

$230
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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From Cleveland Hopkins Intl to Annapolis
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One-way flight from Cleveland Hopkins Intl to Annapolis
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Highest demand for flights based on searches. 14% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Cleveland to Annapolis

Cheapest flights from Cleveland to Annapolis
Explore the most affordable flight options available from Cleveland to Annapolis. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.

This Frontier deal was found by Cheapflights users on 10/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/101:41 pmCLE - BWI
1 stop10h 43mFrontier
Thu 12/115:55 amBWI - CLE
1 stop9h 53mFrontier
Deal found 10/27$110
This Frontier deal was found by Cheapflights users on 10/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:50 amCLE - BWI
1 stop10h 53mFrontier
Mon 12/811:48 amBWI - CLE
1 stop5h 30mFrontier
Deal found 10/26$143
This Priceline deal was found by Cheapflights users on 10/26. 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 11/137:20 amCLE - BWI
1 stop8h 00mFrontier
Sat 11/155:48 amBWI - CLE
1 stop6h 34mFrontier
Deal found 10/26$150
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/101:41 pmCLE - BWI
1 stop10h 43mMultiple Airlines
Mon 12/158:30 pmBWI - CLE
2 stops26h 16mMultiple Airlines
Deal found 10/27$157
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/123:40 pmCLE - BWI
1 stop16h 38mFrontier
Wed 11/1910:00 amBWI - CLE
1 stop24h 32mFrontier
Deal found 10/25$158
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/107:51 pmCLE - BWI
1 stop17h 04mMultiple Airlines
Wed 11/129:36 pmBWI - CLE
1 stop26h 23mMultiple Airlines
Deal found 10/27$160
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/87:20 amCLE - BWI
1 stop13h 11mMultiple Airlines
Tue 11/119:36 pmBWI - CLE
2 stops16h 38mMultiple Airlines
Deal found 10/26$165
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/102:45 pmCLE - BWI
2 stops22h 10mMultiple Airlines
Fri 11/144:55 pmBWI - CLE
1 stop7h 59mMultiple Airlines
Deal found 10/26$169
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/113:40 pmCLE - BWI
1 stop21h 15mMultiple Airlines
Wed 11/129:36 pmBWI - CLE
1 stop26h 23mMultiple Airlines
Deal found 10/27$171
This Booking.com deal was found by Cheapflights users on 10/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/121:46 pmCLE - BWI
1 stop18h 48mFrontier
Sat 11/155:48 amBWI - CLE
1 stop6h 34mFrontier
Deal found 10/26$172
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/79:00 pmCLE - BWI
1 stop12h 21mFrontier
Sun 11/99:59 pmBWI - CLE
1 stop13h 18mFrontier
Deal found 10/28$176
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:55 pmCLE - IAD
Nonstop1h 20mUnited Airlines
Wed 3/1810:05 pmIAD - CLE
Nonstop1h 23mUnited Airlines
Deal found 10/27$189

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cleveland 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 October 28, 2025.
Use the filters below to find and compare flights from Cleveland to Annapolis that are best for you.

Fly from

Cleveland

Fly to

Annapolis

Route

Depart

Return

Price

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

Mon 11/10

7:20 am-3:35 pm

1 stop8h 15m

Baltimore/Washington

Fri 11/14

4:30 pm-12:54 am

1 stop8h 24m

$143

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

Wed 11/12

3:40 pm-8:18 am

1 stop16h 38m

Baltimore/Washington

Wed 11/19

10:00 am-8:17 am

2 stops22h 17m

$180

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Fri 12/5

7:55 pm-9:15 pm

Nonstop1h 20m

Washington, D.C. Dulles Intl

Sun 12/7

8:20 am-9:46 am

Nonstop1h 26m

$189

ClevelandWashington, D.C.

CLE - DCA

CLEDCA

Cleveland Hopkins Intl

Wed 11/19

12:20 pm-1:45 pm

Nonstop1h 25m

Washington, D.C. Reagan-National

Sun 11/23

10:23 pm-11:59 pm

Nonstop1h 36m

$189

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Wed 12/3

7:55 pm-9:15 pm

Nonstop1h 20m

Washington, D.C. Dulles Intl

Wed 3/18

12:35 pm-2:06 pm

Nonstop1h 31m

$189

ClevelandWashington, D.C.

CLE - DCA

CLEDCA

Cleveland Hopkins Intl

Wed 12/17

7:36 pm-9:07 pm

Nonstop1h 31m

Washington, D.C. Reagan-National

Sun 1/11

10:20 pm-11:57 pm

Nonstop1h 37m

$189

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Fri 11/28

6:00 am-7:19 am

Nonstop1h 19m

Washington, D.C. Dulles Intl

Mon 12/1

8:20 am-9:35 am

Nonstop1h 15m

$189

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Tue 12/23

6:00 am-7:29 am

Nonstop1h 29m

Washington, D.C. Dulles Intl

Tue 12/30

12:50 pm-2:20 pm

Nonstop1h 30m

$189

ClevelandWashington, D.C.

CLE - DCA

CLEDCA

Cleveland Hopkins Intl

Fri 11/14

7:36 pm-9:07 pm

Nonstop1h 31m

Washington, D.C. Reagan-National

Sun 11/16

10:10 pm-11:45 pm

Nonstop1h 35m

$194

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Fri 11/14

10:37 am-11:55 am

Nonstop1h 18m

Washington, D.C. Dulles Intl

Wed 11/19

8:15 am-9:35 am

Nonstop1h 20m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 60 results
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Best time to book a flight from Cleveland to Annapolis

Have a flexible travel schedule? Discover the best time to fly to Annapolis from Cleveland 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 Cleveland to Annapolis

How far ahead should I book a flight from Cleveland to Annapolis?

Use this chart to determine the optimal time to book a round-trip flight from Cleveland to Annapolis. Price data was last updated on October 24, 2025.

The price you pay for your flight from Cleveland to Annapolis may vary depending on when you book. For the best chance of a lower fare, look to book 57 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Cleveland to Annapolis?

Currently, August is the cheapest month in which you can book a flight from Cleveland to Annapolis (average of $42). Flying from Cleveland to Annapolis in April is currently the most expensive (average of $78). 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 CLE to AP9?

Find hourly flight availability from Cleveland 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 October 28, 2025.

It’s optimal to fly from Cleveland to Annapolis in the morning. By choosing this option you can save up to 30% on the cost of your flight, compared to a flight in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Cleveland to Annapolis. Price data was last updated on October 26, 2025.

Travelers seeking maximum savings on their Cleveland to Annapolis flight should consider departing on Friday evenings 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 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 October 28, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American 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
4,235 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,996 reviews
Southwest
8.0
Very good
4,235 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,033 reviews
Southwest
8.0
Very good
4,235 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,122 reviews
Southwest
8.0
Very good
4,235 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Cleveland 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 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. 4 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.

  • How long is the flight from Cleveland to Annapolis?

    Frontier, United Airlines, and American Airlines can get you from Cleveland to Annapolis in just under 1h 20m. Your travel time can differ by up to 6h 55m. Cleveland and Annapolis are separated by a distance of 288 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 Cleveland to Annapolis one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $68. However, be on the lookout for offers from United Airlines and Delta, 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 - Baltimore/Washington and Cleveland Hopkins Intl - Washington, D.C. Reagan-National.

  • 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%), Mesa Airlines (100%), Avianca (98%).

  • What are the cheapest flights from Cleveland to Annapolis?

    Looking for the cheapest flight from Cleveland to Annapolis? While on average our users pay $1,120, our data indicates the cheapest price to be $128. The most popular route (Cleveland Hopkins Intl - Washington, D.C. Dulles Intl), is priced around $189.

  • 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.

  • What is the cheapest month to book a flight from Cleveland to Annapolis?

    Currently, August is the cheapest month in which you can book a flight from Cleveland to Annapolis (average of $42). Flying from Cleveland to Annapolis in April is currently the most expensive (average of $78). 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 Cleveland to Annapolis

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Cleveland to Annapolis

Discover the top 4 airlines that operate flights from Cleveland 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$189FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$188Average$268FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$284FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$191Average$297FlexibilityNo cancel feeOn-time63%

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