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$85+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — BWI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Annapolis are usually found in August or May, booked 88 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 July 30, 2025.

Round-trip from

$177
(Southwest)

One-way from

$85
(Mytrip)

Popular in

April

Cheapest in

August

Average price

$249
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. 10% potential increase in price ($29 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 July 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 July 30, 2025.

This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/265:35 amCLE - BWI
Nonstop1h 20mSouthwest
Tue 9/28:45 pmBWI - CLE
Nonstop1h 25mSouthwest
Deal found 7/28$177
This Frontier deal was found by Cheapflights users on 7/28. 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.
Wed 7/306:56 pmCLE - BWI
1 stop5h 29mFrontier
Sat 8/26:45 amBWI - CLE
1 stop11h 29mFrontier
Deal found 7/28$178
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 8/2110:35 amCLE - IAD
Nonstop1h 17mUnited Airlines
Mon 8/258:20 amIAD - CLE
Nonstop1h 19mUnited Airlines
Deal found 7/30$189
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/298:04 pmCLE - DCA
Nonstop1h 25mAmerican Airlines
Sun 8/3111:34 amDCA - CLE
Nonstop1h 26mAmerican Airlines
Deal found 7/28$189
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/283:00 pmCLE - BWI
1 stop8h 59mSpirit Airlines
Thu 9/49:38 amBWI - CLE
2 stops23h 13mSpirit Airlines
Deal found 7/28$190
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/131:47 pmCLE - BWI
2 stops9h 50mDelta
Tue 9/1612:17 pmBWI - CLE
1 stop4h 46mDelta
Deal found 7/28$192
This FlightHub deal was found by Cheapflights users on 7/30. 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.
Sat 8/168:20 amCLE - IAD
1 stop10h 10mFrontier
Sun 8/175:59 pmIAD - CLE
1 stop6h 15mFrontier
Deal found 7/30$195
This Delta deal was found by Cheapflights users on 7/30. 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.
Sat 8/306:55 pmCLE - IAD
1 stop4h 31mDelta
Tue 9/26:00 amIAD - CLE
1 stop3h 16mDelta
Deal found 7/30$197
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/209:00 amCLE - DCA
1 stop7h 00mSouthwest
Sat 8/232:45 pmDCA - CLE
1 stop7h 00mSouthwest
Deal found 7/28$197
This Delta deal was found by Cheapflights users on 7/29. 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.
Sat 8/306:40 pmCLE - DCA
1 stop5h 01mDelta
Sun 8/319:40 amDCA - CLE
1 stop3h 52mDelta
Deal found 7/29$198
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 8/2112:23 pmCLE - DCA
1 stop3h 58mUnited Airlines
Mon 8/2511:10 amDCA - CLE
1 stop4h 54mUnited Airlines
Deal found 7/30$209
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Fri 9/266:00 amCLE - BWI
1 stop4h 13mAmerican Airlines
Tue 9/3010:05 amBWI - CLE
1 stop5h 36mAmerican Airlines
Deal found 7/30$213

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 July 30, 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

Tue 8/26

5:35 am-6:55 am

Nonstop1h 20m

Baltimore/Washington

Wed 8/27

9:40 am-11:00 am

Nonstop1h 20m

$177

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

Sat 8/2

5:30 am-4:54 pm

1 stop11h 24m

Baltimore/Washington

Tue 8/5

7:15 am-6:03 pm

1 stop10h 48m

$178

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Thu 8/21

10:35 am-11:52 am

Nonstop1h 17m

Washington, D.C. Dulles Intl

Mon 8/25

8:20 am-9:39 am

Nonstop1h 19m

$189

ClevelandWashington, D.C.

CLE - DCA

CLEDCA

Cleveland Hopkins Intl

Fri 8/29

8:04 pm-9:29 pm

Nonstop1h 25m

Washington, D.C. Reagan-National

Sun 8/31

11:34 am-1:00 pm

Nonstop1h 26m

$189

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

Thu 8/28

3:00 pm-11:59 pm

1 stop8h 59m

Baltimore/Washington

Thu 9/4

9:38 am-8:51 am

2 stops23h 13m

$190

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

Sat 9/13

1:47 pm-11:37 pm

2 stops9h 50m

Baltimore/Washington

Tue 9/16

12:17 pm-5:03 pm

1 stop4h 46m

$192

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Sat 8/16

8:20 am-6:30 pm

1 stop10h 10m

Washington, D.C. Dulles Intl

Sun 8/17

5:59 pm-12:14 am

1 stop6h 15m

$195

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Sat 8/30

6:55 pm-11:26 pm

1 stop4h 31m

Washington, D.C. Dulles Intl

Tue 9/2

6:00 am-9:16 am

1 stop3h 16m

$197

ClevelandWashington, D.C.

CLE - DCA

CLEDCA

Cleveland Hopkins Intl

Wed 8/20

9:00 am-4:00 pm

1 stop7h 00m

Washington, D.C. Reagan-National

Sat 8/23

2:45 pm-9:45 pm

1 stop7h 00m

$197

ClevelandWashington, D.C.

CLE - DCA

CLEDCA

Cleveland Hopkins Intl

Sat 8/30

6:40 pm-11:41 pm

1 stop5h 01m

Washington, D.C. Reagan-National

Sun 8/31

9:40 am-1:32 pm

1 stop3h 52m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 28 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 July 25, 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 88 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 $241). Flying from Cleveland 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 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 July 30, 2025.

When flying from Cleveland to Annapolis, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 July 27, 2025.

Travelers seeking maximum savings on their Cleveland to Annapolis flight should consider departing on Friday mornings when fares are most often at their lowest. Monday at noon 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 July 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United 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
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 16 outbound flights to Annapolis per day.

  • How popular is this Cleveland to Annapolis flight route?

    The Cleveland Hopkins Intl to Annapolis flight path was viewed by 81 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 Cleveland to Annapolis one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $85. However, be on the lookout for offers from Frontier and Southwest, 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. Reagan-National, Cleveland Hopkins Intl - Baltimore/Washington and Cleveland Hopkins Intl - Washington, D.C. Dulles Intl.

  • What are the cheapest flights from Cleveland to Annapolis?

    Looking for the cheapest flight from Cleveland to Annapolis? While on average our users pay $249, our data indicates the cheapest price to be $75. The most popular route (Cleveland Hopkins Intl - Washington, D.C. Reagan-National), is priced around $197.

  • 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 $241). Flying from Cleveland 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.

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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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$103Average$218FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$188Average$279FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$196Average$310FlexibilityNo cancel feeOn-time69%
DeltaCheapest$198Average$243FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$201Average$305FlexibilityNo cancel feeOn-time63%

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