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$78+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — BWI
ago. 18 — ago. 251
lun. 8/18
lun. 8/25
1 adult, Economy
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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Annapolis are usually found in May or August, 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 agosto 13, 2025.

Round-trip from

$155
(Southwest)

One-way from

$78
(United Airlines)

Popular in

April

Cheapest in

May

Average price

$227
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. 9% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 13, 2025.

This Southwest deal was found by Cheapflights users on 8/11. 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.
mar. 9/95:35 amCLE - BWI
Nonstop1h 20mSouthwest
jue. 9/119:50 pmBWI - CLE
Nonstop1h 20mSouthwest
Deal found 8/11$166
This Southwest deal was found by Cheapflights users on 8/12. 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.
mié. 9/245:35 amCLE - BWI
Nonstop1h 20mSouthwest
dom. 9/2810:55 pmBWI - CLE
Nonstop1h 20mSouthwest
Deal found 8/12$175
This Southwest deal was found by Cheapflights users on 8/12. 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.
lun. 9/87:35 pmCLE - BWI
1 stop3h 50mSouthwest
mié. 9/109:40 amBWI - CLE
Nonstop1h 20mSouthwest
Deal found 8/12$176
This Southwest deal was found by Cheapflights users on 8/12. 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.
jue. 9/45:50 amCLE - BWI
Nonstop1h 20mSouthwest
lun. 9/83:30 pmBWI - CLE
Nonstop1h 20mSouthwest
Deal found 8/12$177
This American Airlines deal was found by Cheapflights users on 8/10. 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.
mar. 9/96:00 amCLE - BWI
1 stop4h 13mAmerican Airlines
jue. 9/116:52 pmBWI - CLE
1 stop5h 26mAmerican Airlines
Deal found 8/10$181
This Delta deal was found by Cheapflights users on 8/10. 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.
mié. 12/1712:00 pmCLE - BWI
1 stop5h 04mDelta
mié. 1/78:10 amBWI - CLE
1 stop5h 16mDelta
Deal found 8/10$182
This Southwest deal was found by Cheapflights users on 8/11. 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.
jue. 9/115:50 amCLE - BWI
Nonstop1h 20mSouthwest
dom. 9/1410:55 amBWI - CLE
Nonstop1h 20mSouthwest
Deal found 8/11$186
This Delta deal was found by Cheapflights users on 8/12. 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.
jue. 9/44:33 pmCLE - BWI
1 stop4h 42mDelta
lun. 9/87:29 pmBWI - CLE
1 stop5h 11mDelta
Deal found 8/12$187
This American Airlines deal was found by Cheapflights users on 8/10. 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.
vie. 8/298:04 pmCLE - DCA
Nonstop1h 25mAmerican Airlines
lun. 9/16:58 amDCA - CLE
Nonstop1h 38mAmerican Airlines
Deal found 8/10$188
This United Airlines deal was found by Cheapflights users on 8/12. 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.
vie. 9/128:00 pmCLE - IAD
Nonstop1h 17mUnited Airlines
dom. 9/1412:46 pmIAD - CLE
Nonstop1h 18mUnited Airlines
Deal found 8/12$189
This American Airlines deal was found by Cheapflights users on 8/10. 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.
vie. 9/2612:57 pmCLE - DCA
Nonstop1h 27mAmerican Airlines
dom. 9/289:59 pmDCA - CLE
Nonstop1h 39mAmerican Airlines
Deal found 8/10$189
This American Airlines deal was found by Cheapflights users on 8/11. 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.
jue. 9/46:00 amCLE - DCA
Nonstop1h 28mAmerican Airlines
lun. 9/82:59 pmDCA - CLE
Nonstop1h 35mAmerican Airlines
Deal found 8/11$190

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 agosto 13, 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

mar. 9/9

5:35 am-6:55 am

Nonstop1h 20m

Baltimore/Washington

mar. 9/16

8:45 pm-10:10 pm

Nonstop1h 25m

$155

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

mar. 9/9

5:35 am-6:55 am

Nonstop1h 20m

Baltimore/Washington

jue. 9/11

9:50 pm-11:10 pm

Nonstop1h 20m

$166

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

lun. 10/20

5:45 am-7:00 am

Nonstop1h 15m

Baltimore/Washington

mié. 10/22

9:05 am-10:25 am

Nonstop1h 20m

$166

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

mar. 9/9

6:00 am-10:13 am

1 stop4h 13m

Baltimore/Washington

mar. 9/16

11:04 am-3:41 pm

1 stop4h 37m

$175

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

mar. 9/9

1:24 pm-5:41 pm

1 stop4h 17m

Baltimore/Washington

mié. 9/10

6:16 am-12:31 pm

1 stop6h 15m

$175

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

mié. 9/24

5:35 am-6:55 am

Nonstop1h 20m

Baltimore/Washington

dom. 9/28

10:55 pm-12:15 am

Nonstop1h 20m

$175

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

lun. 9/8

4:25 pm-5:45 pm

Nonstop1h 20m

Baltimore/Washington

mié. 9/10

9:40 am-11:00 am

Nonstop1h 20m

$175

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

mié. 9/3

5:35 am-6:55 am

Nonstop1h 20m

Baltimore/Washington

vie. 9/5

9:50 pm-11:10 pm

Nonstop1h 20m

$175

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

dom. 9/14

5:30 am-6:50 am

Nonstop1h 20m

Baltimore/Washington

mié. 9/17

5:00 pm-6:20 pm

Nonstop1h 20m

$175

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

mar. 10/21

10:35 am-11:53 am

Nonstop1h 18m

Washington, D.C. Dulles Intl

dom. 10/26

8:20 am-9:41 am

Nonstop1h 21m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

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 August 8, 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 agosto 13, 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 August 10, 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 agosto 13, 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
4,246 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
8,920 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
4,246 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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.
Frontier
5.8
Fair
3,221 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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 19 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 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 cheapest flights from Cleveland to Annapolis?

    Looking for the cheapest flight from Cleveland to Annapolis? While on average our users pay $253, our data indicates the cheapest price to be $75. The most popular route (Cleveland Hopkins Intl - Washington, D.C. Dulles Intl), is priced around $184.

  • 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.

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 agosto 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$218FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$188Average$279FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$193Average$309FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$196Average$304FlexibilityNo cancel feeOn-time63%
DeltaCheapest$198Average$243FlexibilityNo cancel feeOn-timeN/A

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