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Find cheap flights from Cleveland to Annapolis from $39

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Cleveland to Annapolis departing on 6/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Tue 7/9
Tue 7/16

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Good to know

Low season

December

High season

May

Cheapest flight

$39
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Cleveland to Baltimore

When to book flights from Cleveland to Annapolis

Are your dates flexible? Find out the best times to travel from Cleveland to Annapolis based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Cleveland to Annapolis

  • Which airports will I be using when flying from Cleveland to Annapolis?

    When flying out of Cleveland you’ll be using Cleveland Hopkins Intl. Annapolis does not have its own airport so you’ll be flying into nearby Washington, D.C. All airports airport, which is 29.8 mi away.

  • How long does a flight from Cleveland to Annapolis take?

    Direct flights cover the 307 miles separating Cleveland and Annapolis in about 1h 16m.

  • How many flights are there between Cleveland and Annapolis?

    32 direct flights run between Cleveland and Annapolis on a daily basis. On average, there are about 226 departures each week.

  • What’s the cheapest day of the week to fly between Cleveland and Annapolis?

    Consider leaving on a Tuesday and avoid Thursdays if you are looking for the best rates. For your return to Cleveland, you’ll find the best rates on Tuesdays and the most expensive ones on Thursdays.

  • How does KAYAK find such low prices on flights from Cleveland to Annapolis?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Cleveland to Annapolis.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Cleveland to Annapolis?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Annapolis from Cleveland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Cleveland to Annapolis?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Annapolis with an airline and back to Cleveland with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Cleveland to Annapolis?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Annapolis from Cleveland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Cleveland to Annapolis?

    In the last 72 hours, the cheapest one-way ticket between Cleveland and Annapolis found on KAYAK was with Frontier for $39. Frontier offered a round-trip connection from $78 and American Airlines from $117.

See more FAQs

Top tips for finding cheap flights from Cleveland to Annapolis

  • There is no airport in Annapolis. Instead, you’ll be flying into Washington, D.C. All airports when flying between Cleveland and Annapolis.
  • The cheapest flight from Cleveland to Annapolis was found 68 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be May, June and July. The cheapest month to fly is January.
See more tips

Top 4 airlines serving Cleveland to Annapolis

Need help choosing which airline to fly with from Cleveland to Annapolis? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 10661 reviews
8.1Crew
6.7Food
7.7Boarding
7.2Comfort
7.1Entertainment
Airline reviews

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

4.0 OkayJames, Jun 2024RIC - ORD
Read more about United Airlines reviews

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

Original plane sidelined. Had to wait an hour for replacement.

Crew was very cooperative and professional. Passenger's first checked in bag should be free.

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

Horrible, the flights kept delaying, so it is obvious that we won't be able to make it to the next connection. No easier/real agent on site to help you figure this out. UA agent on other counters refuse to assist you and direct us to use the QR code/call customer service. So inefficient and poor. While technology seems convenient, but it's not the best interest/experience for customers need help while there is active issue need assistance.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

My window shade didn’t work. So I missed coming into my city. ☹️

Flight was delayed in the gate by 5 hours and ultimately cancelled- rebooking service by United agents was terrible

Flight was delayed due to the late arrival of the catering truck, which is quite unacceptable. There was a beverage service, but no pretzel, or cookie, or nuts were served in coach.

Not worth the price of premium class ticket paid, felt more like steerage.

This is by far the worst experience I have had with American Airlines. The start of this trip was a complete disaster. I purposely planned my trip so that I would weather any delays so that I could make very important meeting at the Pentagon. My flight was cancelled because of maintenance and I was put on the first flight the next day but I was late to the meeting. After a long week at the Pentagon I just wanted to go home and my flight home which was early in the day was delayed. Eventually the flight was delayed until the next day. I was not authorized a hotel room because DCA was my point of origin. So I paid for a hotel out of pocket. The flight this morning was boarded then deplaned because the aircraft was hot. The flow of information was not happening in DCA and made it worse when the news was bad. I am going to take a break from American for my next few military flights. Hopefully whatever has been going on with American Airlines will be resolved.

We had a 2 hour delay. The seats were smaller than most other airlines. The person in front of us wanted to lay back and we had to stop her because she was pressing against my girlfriend’s legs. We had to ask her to sit up and not lay back due to the lack of room.

Everything was fine once we actually got on our flight. It was more then annoying they canceled (delayed) our flight. We lost out on a day of our trip along with money on our stay. Plus we had to book another hotel. So expensive.

This flight was canceled and delayed several times without explanation. The plane was freezing cold and no wifi for messaging. Getting off the plane was terribly unorganized and felt like it took forever….

The flight was delayed several times without explanation. The seats were terribly uncomfortable and wifi isn’t included. All these make for a less than ideal flight.

The flights was delayed by hours and it was the firmest landing I have experienced in my life. My back is still sore.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Terrible. I didn’t fly and I had an important meeting the next day.

Equipment swap led to 2+ hour delay on international flight. And to top it off, boarding took forever.

Wretched scheduling - they got themselves into a critical crew situation and didn’t try to address it until 15 minutes before they had to cancel my flight

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

The weight limit per bag was really low - 40 lbs - so we had to pay extra. Then, they said their carry on size was 14x18x8, and we measured our bag very carefully. It was within the limit, yet they said it was too big, so we ended up paying an extra $100 for that too!! So it wasn’t the cheap flight we thought it would be. Then, they moved up our initial flight to depart 3 hours earlier which meant we had to be out on the road by 7 am and then have a 6 hour layover and we got home at 2am. It was a grueling day. I won’t be flying with them again.

They seemingly have no respect for their customers, on any level. Avoid flying spirit, they will bump you to another flight without thinking twice so they can sell your seat, no joke.

One hour late taking off. Concerning, very hard landing. Uncomfortable seats with no recline. Extremely slow baggage claim. Very professional, knowledgeable flight attendants. Brand new, very clean plane.

Early departure and arrival. Cabin very cold. Waited a while for luggage to come out

The price was good, but the seats was too little too cramped. You guys nickel and dime the person who’s flying all food even water that’s ridiculous. I’ll be flying with somebody else unless this changes.

I liked that bag check was rather quick and efficient. The airplane chairs on the first leg of the trip were hard and uncomfortable. Also, the cabin temperature was too cold. The lady giving seat assignments took entirely too long. She said she would call me back to the desk in 5 minutes, and she never called me back.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

Book cheap flights from Cleveland to Annapolis

Recent round-trip flight deals

7/9Tue
nonstopFrontier
1h 17mCLE-BWI
7/16Tue
nonstopFrontier
1h 17mBWI-CLE
$78
9/12Thu
nonstopFrontier
1h 18mCLE-BWI
9/15Sun
nonstopFrontier
1h 18mBWI-CLE
$88
7/9Tue
nonstop
1h 17mCLE-BWI
7/16Tue
1 stop
6h 28mBWI-CLE
$114
8/6Tue
nonstopAmerican Airlines
1h 27mCLE-DCA
8/13Tue
nonstopAmerican Airlines
1h 24mDCA-CLE
$117
7/9Tue
nonstopUnited Airlines
1h 18mCLE-IAD
7/10Wed
nonstopUnited Airlines
1h 19mIAD-CLE
$117
8/20Tue
nonstopAmerican Airlines
1h 26mCLE-DCA
8/23Fri
nonstopAmerican Airlines
1h 28mDCA-CLE
$127
9/9Mon
1 stopSpirit Airlines
13h 10mCLE-BWI
9/24Tue
1 stopSpirit Airlines
12h 04mBWI-CLE
$133
8/22Thu
nonstopUnited Airlines
1h 19mCLE-IAD
8/22Thu
nonstopUnited Airlines
1h 18mIAD-CLE
$137
8/6Tue
1 stop
12h 11mCLE-BWI
8/13Tue
nonstop
1h 18mBWI-CLE
$142
7/10Wed
1 stopSpirit Airlines
16h 19mCLE-BWI
7/11Thu
1 stopSpirit Airlines
6h 40mBWI-CLE
$150

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Recent one-way flight deals

6/18Tue
nonstopFrontier
1h 16mCLE-BWI
$39
6/25Tue
nonstopFrontier
1h 16mCLE-BWI
$42
6/18Tue
2 stopsSpirit Airlines
19h 09mCLE-BWI
$58
6/27Thu
1 stopSpirit Airlines
5h 34mCLE-BWI
$64
7/10Wed
1 stopDelta
6h 28mCLE-IAD
$78
7/10Wed
1 stopDelta
4h 57mCLE-DCA
$78
7/10Wed
nonstopUnited Airlines
1h 18mCLE-IAD
$89
7/4Thu
nonstopAmerican Airlines
1h 25mCLE-DCA
$90
7/2Tue
nonstopUnited Airlines
1h 23mCLE-IAD
$90
7/27Sat
nonstopAmerican Airlines
1h 27mCLE-DCA
$95

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Last minute flights from Cleveland to Annapolis

Last minute flight, train and bus deals

6/11Tue
nonstopFrontier
1h 16mCLE-BWI
6/18Tue
nonstopFrontier
1h 16mBWI-CLE
$118
6/11Tue
nonstop
1h 16mCLE-BWI
6/18Tue
multi-stop
8h 29mBWI-CLE
$131
6/13Thu
multi-stopSpirit Airlines
5h 34mCLE-BWI
6/17Mon
multi-stopSpirit Airlines
17h 45mBWI-CLE
$297
6/13Thu
multi-stopSpirit Airlines
5h 34mCLE-BWI
6/17Mon
multi-stopSpirit Airlines
17h 45mBWI-CLE
$319
6/13Thu
nonstopAmerican Airlines
1h 28mCLE-DCA
7/1Mon
nonstopAmerican Airlines
1h 25mDCA-CLE
$394
6/13Thu
nonstopUnited Airlines
1h 18mCLE-IAD
7/1Mon
nonstopUnited Airlines
1h 19mIAD-CLE
$394
6/13Thu
multi-stopAmerican Airlines
3h 37mCLE-DCA
7/1Mon
nonstopAmerican Airlines
1h 26mDCA-CLE
$404
6/13Thu
multi-stopUnited Airlines
4h 09mCLE-IAD
7/1Mon
nonstopUnited Airlines
1h 19mIAD-CLE
$404
6/14Fri
multi-stopDelta
5h 09mCLE-IAD
6/17Mon
multi-stopDelta
3h 28mIAD-CLE
$518
6/13Thu
multi-stopDelta
7h 00mCLE-DCA
6/20Thu
multi-stopDelta
6h 46mDCA-CLE
$518

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Flights to Annapolis