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$49+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — IAD
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Annapolis are usually found in May or October, booked 57 days in advance, depart on a Friday or Thursday and return on a Saturday

Cheap 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 January 28, 2026.

This Southwest deal was found by Cheapflights users on 1/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/174:35 pm
CLE
-
BWI
Nonstop1h 20m
Southwest
Tue 3/179:40 pm
BWI
-
CLE
Nonstop1h 20m
Southwest
Deal found 1/27$97
This Frontier deal was found by Cheapflights users on 1/27. 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.
Tue 2/249:30 am
CLE
-
BWI
1 stop7h 43m
Frontier
Wed 2/258:25 pm
BWI
-
CLE
1 stop11h 31m
Frontier
Deal found 1/27$128
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Mon 2/232:40 pm
CLE
-
BWI
1 stop26h 33m
Frontier
Mon 3/26:08 pm
BWI
-
CLE
1 stop13h 26m
Frontier
Deal found 1/25$131
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sat 2/218:50 am
CLE
-
BWI
1 stop15h 41m
Frontier
Mon 2/236:08 pm
BWI
-
CLE
1 stop13h 26m
Frontier
Deal found 1/27$133
This Expedia deal was found by Cheapflights users on 1/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/199:23 am
CLE
-
BWI
1 stop22h 26m
Frontier
Sat 2/215:57 pm
BWI
-
CLE
1 stop15h 14m
Frontier
Deal found 1/26$138
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Fri 2/272:40 pm
CLE
-
BWI
1 stop9h 51m
Multiple Airlines
Sat 2/2812:30 pm
BWI
-
CLE
2 stops10h 51m
Multiple Airlines
Deal found 1/27$144
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Sun 3/18:45 pm
CLE
-
BWI
1 stop27h 46m
Multiple Airlines
Wed 3/410:06 am
BWI
-
CLE
1 stop8h 03m
Multiple Airlines
Deal found 1/25$148
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Wed 2/257:00 am
CLE
-
BWI
1 stop10h 47m
Multiple Airlines
Wed 3/46:20 am
BWI
-
CLE
2 stops12h 54m
Multiple Airlines
Deal found 1/26$150
This Frontier deal was found by Cheapflights users on 1/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/127:15 am
CLE
-
BWI
1 stop9h 58m
Frontier
Thu 2/195:45 am
BWI
-
CLE
1 stop12h 07m
Frontier
Deal found 1/25$154
This United Airlines deal was found by Cheapflights users on 1/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:00 am
CLE
-
IAD
Nonstop1h 20m
United Airlines
Sun 3/1510:20 pm
IAD
-
CLE
Nonstop1h 23m
United Airlines
Deal found 1/26$189
This American Airlines deal was found by Cheapflights users on 1/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:52 am
CLE
-
DCA
Nonstop1h 23m
American Airlines
Wed 10/1411:00 am
DCA
-
CLE
Nonstop1h 21m
American Airlines
Deal found 1/25$189
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:36 pm
CLE
-
IAD
1 stop3h 33m
Delta
Mon 2/236:00 am
IAD
-
CLE
1 stop3h 48m
Delta
Deal found 1/27$191

Find flight deals from Cleveland to Annapolis

Keep the following information in mind while searching for Cleveland to Annapolis flight deals. Data was last updated January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

March

Cheapest in

May

Average price

$259
Provider with most accurate pricing for Cleveland Hopkins Intl-Washington, D.C. (WAS) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-Washington, D.C. (WAS) flights.
Search Deals
From Cleveland Hopkins Intl to Annapolis
Search Deals
One-way flight from Cleveland Hopkins Intl to Annapolis
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 28, 2026.
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

Tue 3/17

4:35 pm-5:55 pm

Nonstop1h 20m

Baltimore/Washington

Tue 3/17

9:40 pm-11:00 pm

Nonstop1h 20m

$97

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

Thu 2/19

5:45 am-7:15 am

Nonstop1h 30m

Baltimore/Washington

Sat 2/21

10:40 am-12:05 pm

Nonstop1h 25m

$171

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

Thu 2/26

5:30 am-7:10 am

Nonstop1h 40m

Baltimore/Washington

Thu 3/5

6:40 am-1:55 pm

1 stop7h 15m

$181

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

Sat 2/21

6:05 am-11:20 am

1 stop5h 15m

Baltimore/Washington

Mon 2/23

10:45 am-12:10 pm

Nonstop1h 25m

$181

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Fri 3/6

6:00 am-7:20 am

Nonstop1h 20m

Washington, D.C. Dulles Intl

Sun 3/15

10:20 pm-11:43 pm

Nonstop1h 23m

$189

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Fri 5/1

3:06 pm-4:26 pm

Nonstop1h 20m

Washington, D.C. Dulles Intl

Sun 5/3

12:40 pm-2:04 pm

Nonstop1h 24m

$189

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Wed 7/1

6:00 am-7:35 am

Nonstop1h 35m

Washington, D.C. Dulles Intl

Sun 7/5

12:35 pm-1:56 pm

Nonstop1h 21m

$189

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Fri 4/24

6:00 am-7:20 am

Nonstop1h 20m

Washington, D.C. Dulles Intl

Sun 4/26

10:33 pm-11:59 pm

Nonstop1h 26m

$189

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Sat 6/13

10:36 am-11:52 am

Nonstop1h 16m

Washington, D.C. Dulles Intl

Sun 6/21

8:15 am-9:36 am

Nonstop1h 21m

$189

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Mon 6/22

6:00 am-7:35 am

Nonstop1h 35m

Washington, D.C. Dulles Intl

Tue 6/30

8:15 am-9:27 am

Nonstop1h 12m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 56 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 January 23, 2026.

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, January is the cheapest month in which you can book a flight from Cleveland to Annapolis (average of $41). Flying from Cleveland to Annapolis in April is currently the most expensive (average of $81). 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 January 28, 2026.

It’s optimal to fly from Cleveland to Annapolis in the morning. By choosing this option you can save up to 32% 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 January 24, 2026.

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.

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

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 January 28, 2026.
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
4,268 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,208 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,201 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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. 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 13 outbound flights to Annapolis per day.

  • How long is the flight from Cleveland to Annapolis?

    Southwest, United Airlines, and Delta can get you from Cleveland to Annapolis in just under 1h 20m. Your travel time can differ by up to 4h 35m. Cleveland and Annapolis are separated by a distance of 313 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 American Airlines, with whom users have recently found tickets for as low as $84. However, be on the lookout for offers from Frontier and United 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 - 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: CommutAir (100%), Ethiopian Air (92%), Republic Airways (88%).

  • What are the cheapest flights from Cleveland to Annapolis?

    Looking for the cheapest flight from Cleveland to Annapolis? While on average our users pay $1,078, our data indicates the cheapest price to be $158. The most popular route (Cleveland Hopkins Intl - Washington, D.C. Dulles Intl), is priced around $134.

  • 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, January is the cheapest month in which you can book a flight from Cleveland to Annapolis (average of $41). Flying from Cleveland to Annapolis in April is currently the most expensive (average of $81). 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 5 airlines flying from Cleveland to Annapolis

Discover the top 5 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$82Average$189FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$159Average$391FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$341FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$191Average$299FlexibilityNo cancel feeOn-time63%
DeltaCheapest$208Average$585FlexibilityNo cancel feeOn-timeN/A

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