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$59+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — IAD
May 31 — Jun 71
Sun 5/31
Sun 6/7
1 adult, Economy
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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Annapolis are usually found in October or May, booked 40 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 May 1, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Thu 6/253:46 pm
CLE
-
BWI
1 stop7h 14m
Frontier
Sat 6/279:32 pm
BWI
-
CLE
1 stop11h 21m
Frontier
Deal found 4/27$121
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:24 pm
CLE
-
BWI
1 stop12h 19m
Frontier
Wed 6/39:23 pm
BWI
-
CLE
1 stop11h 30m
Frontier
Deal found 4/29$123
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 5/268:49 pm
CLE
-
BWI
1 stop10h 54m
Frontier
Sun 5/319:43 pm
BWI
-
CLE
1 stop14h 07m
Frontier
Deal found 4/27$124
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 5/273:36 pm
CLE
-
BWI
1 stop7h 21m
Frontier
Wed 6/38:52 am
BWI
-
CLE
1 stop9h 35m
Frontier
Deal found 4/27$126
This Southwest deal was found by Cheapflights users on 4/27. 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 5/195:50 am
CLE
-
BWI
Nonstop1h 20m
Southwest
Wed 5/208:55 pm
BWI
-
CLE
Nonstop1h 20m
Southwest
Deal found 4/27$137
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 6/305:51 pm
CLE
-
BWI
1 stop22h 31m
Frontier
Wed 7/81:10 pm
BWI
-
CLE
1 stop25h 28m
Frontier
Deal found 4/27$138
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/107:24 pm
CLE
-
BWI
1 stop12h 11m
Frontier
Fri 6/129:32 pm
BWI
-
CLE
1 stop14h 20m
Frontier
Deal found 4/29$140
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 6/63:46 pm
CLE
-
BWI
1 stop7h 11m
Frontier
Tue 6/97:44 pm
BWI
-
CLE
2 stops22h 45m
Frontier
Deal found 5/1$153
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 5/196:01 pm
CLE
-
BWI
1 stop13h 42m
Frontier
Wed 5/209:13 pm
BWI
-
CLE
1 stop14h 37m
Frontier
Deal found 4/27$155
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 8/157:24 pm
CLE
-
BWI
1 stop12h 12m
Frontier
Thu 8/209:32 pm
BWI
-
CLE
1 stop14h 20m
Frontier
Deal found 5/1$157
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/123:46 pm
CLE
-
BWI
1 stop15h 59m
Frontier
Wed 6/171:29 pm
BWI
-
CLE
1 stop7h 26m
Frontier
Deal found 4/30$158
This United Airlines deal was found by Cheapflights users on 4/27. 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 5/276:00 am
CLE
-
IAD
Nonstop1h 15m
United Airlines
Wed 6/312:45 pm
IAD
-
CLE
Nonstop1h 21m
United Airlines
Deal found 4/27$207

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 May 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$121
(Kiwi.com)

One-way from

$59
(Trip.com)

Popular in

April

Cheapest in

October

Average price

$228
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. 1% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 1, 2026.
Use the filters below to find and compare flights from Cleveland to Annapolis that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

Sat 6/6

3:35 pm-4:55 pm

Nonstop1h 20m

Baltimore/Washington

Tue 6/9

6:15 pm-7:40 pm

Nonstop1h 25m

$164

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

Thu 5/21

5:40 am-7:00 am

Nonstop1h 20m

Baltimore/Washington

Mon 5/25

10:40 am-12:00 pm

Nonstop1h 20m

$191

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

Thu 6/4

12:45 pm-11:17 pm

2 stops10h 32m

Baltimore/Washington

Mon 6/8

2:10 pm-11:59 pm

2 stops9h 49m

$212

ClevelandWashington, D.C.

CLE - IAD

CLEIAD

Cleveland Hopkins Intl

Sun 5/17

6:35 am-10:22 am

1 stop3h 47m

Washington, D.C. Dulles Intl

Wed 5/27

6:00 am-9:20 am

1 stop3h 20m

$228

ClevelandWashington, D.C.

CLE - DCA

CLEDCA

Cleveland Hopkins Intl

Thu 5/21

6:05 am-10:17 am

1 stop4h 12m

Washington, D.C. Reagan-National

Mon 5/25

6:05 am-9:20 am

1 stop3h 15m

$240

ClevelandWashington, D.C.

CLE - DCA

CLEDCA

Cleveland Hopkins Intl

Thu 6/4

7:46 pm-10:59 pm

1 stop3h 13m

Washington, D.C. Reagan-National

Sun 6/7

7:59 pm-11:59 pm

1 stop4h 00m

$240

ClevelandWashington, D.C.

CLE - DCA

CLEDCA

Cleveland Hopkins Intl

Tue 6/16

6:00 am-12:46 pm

1 stop6h 46m

Washington, D.C. Reagan-National

Sat 6/20

12:29 pm-7:03 pm

1 stop6h 34m

$241

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

Wed 6/17

10:40 am-12:00 pm

Nonstop1h 20m

Baltimore/Washington

Sun 6/21

7:10 am-12:50 pm

1 stop5h 40m

$250

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

Sun 5/31

5:30 am-6:50 am

Nonstop1h 20m

Baltimore/Washington

Wed 6/3

8:55 pm-10:15 pm

Nonstop1h 20m

$250

ClevelandBaltimore

CLE - BWI

CLEBWI

Cleveland Hopkins Intl

Mon 9/7

3:50 pm-5:10 pm

Nonstop1h 20m

Baltimore/Washington

Tue 9/8

3:40 pm-5:00 pm

Nonstop1h 20m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 60 resultsSorted by cheapest first
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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

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 May 1, 2026.

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?

Use this chart to determine the cheapest time to fly round-trip from Cleveland to Annapolis. Price data was last updated on April 25, 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.

Weekly flight availability from Cleveland to Annapolis

Explore weekly flight availability from Cleveland to Annapolis. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 1, 2026.

The most flights from CLE to AP9 are scheduled on a Friday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

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 May 1, 2026.
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
4,314 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,314 reviews
Southwest
8.0
Very good
4,314 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,679 reviews
Southwest
8.0
Very good
4,314 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,679 reviews
Southwest
8.0
Very good
4,314 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,972 reviews
Southwest
8.0
Very good
4,314 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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. 6 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 20 outbound flights to Annapolis per day.

  • How long is the flight from Cleveland to Annapolis?

    Southwest, Delta, and United Airlines can get you from Cleveland to Annapolis in just under 1h 15m. Your travel time can differ by up to 9h 17m. 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 American Airlines, with whom users have recently found tickets for as low as $78. 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 - 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: CommutAir (100%), ITA Airways (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 $724, our data indicates the cheapest price to be $129. The most popular route (Cleveland Hopkins Intl - Washington, D.C. Dulles Intl), is priced around $155.

  • 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

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Top 6 airlines flying from Cleveland to Annapolis

Discover the top 6 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 May 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$82Average$181FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$113Average$245FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$159Average$309FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$171Average$304FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$189Average$340FlexibilityNo cancel feeOn-time69%
DeltaCheapest$208Average$585FlexibilityNo cancel feeOn-timeN/A

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