$85 Find Cheap Flights from Cleveland to Annapolis

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 11/16. 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.
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Cheap Flights from Cleveland to Annapolis (CLE-WAS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Cleveland to Annapolis that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Cleveland to Annapolis

Mon, Aug 25 - Thu, Aug 28
United Airlines Logo
8:00 pm - 9:17 pmCLE-IAD
1h 17mnonstop
United Airlines Logo
8:20 am - 9:39 amIAD-CLE
1h 19mnonstop
$177United Airlines
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Thu, Aug 21 - Mon, Aug 25
American Airlines Logo
8:04 pm - 9:29 pmCLE-DCA
1h 25mnonstop
American Airlines Logo
6:58 am - 8:36 amDCA-CLE
1h 38mnonstop
$177American Airlines
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Thu, Aug 21 - Mon, Aug 25
Southwest Logo
5:50 am - 7:10 amCLE-BWI
1h 20mnonstop
Southwest Logo
9:50 pm - 11:10 pmBWI-CLE
1h 20mnonstop
$177Southwest
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Sat, Aug 16 - Wed, Aug 20
Frontier Logo
5:30 am - 3:12 pmCLE-IAD
9h 42m1 stop
Frontier Logo
9:30 am - 3:02 pmIAD-CLE
5h 32m1 stop
$178Frontier
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Sat, Aug 16 - Tue, Aug 19
Frontier Logo
8:20 am - 3:12 pmCLE-BWI
6h 52m1 stop
Frontier Logo
9:30 am - 3:02 pmBWI-CLE
5h 32m1 stop
$178Frontier
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Thu, Sep 4 - Sun, Sep 7
American Airlines Logo
6:00 am - 7:28 amCLE-DCA
1h 28mnonstop
American Airlines Logo
11:00 am - 12:27 pmDCA-CLE
1h 27mnonstop
$183American Airlines
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Wed, Sep 3 - Sun, Sep 7
United Airlines Logo
10:35 am - 11:52 amCLE-IAD
1h 17mnonstop
United Airlines Logo
12:46 pm - 2:04 pmIAD-CLE
1h 18mnonstop
$183United Airlines
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Mon, Aug 25 - Tue, Aug 26
Southwest Logo
5:50 am - 7:10 amCLE-BWI
1h 20mnonstop
Southwest Logo
9:40 am - 11:00 amBWI-CLE
1h 20mnonstop
$186Southwest
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Thu, Aug 21 - Mon, Aug 25
Delta Logo
5:30 am - 9:00 amCLE-BWI
3h 30m1 stop
Delta Logo
12:17 pm - 5:23 pmBWI-CLE
5h 06m1 stop
$187Delta
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Thu, Aug 21 - Mon, Aug 25
Delta Logo
5:30 am - 9:00 amCLE-BWI
3h 30m1 stop
Delta Logo
5:40 am - 1:32 pmBWI-CLE
7h 52m2 stops
$192Delta
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Good to know

Low seasonJanuary
Cheapest flight$85
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 21% 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 14m.

  • How many flights are there between Cleveland and Annapolis?

    34 direct flights run between Cleveland and Annapolis on a daily basis. On average, there are about 239 departures each week.

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

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

  • 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 Spirit Airlines for $85. American Airlines offered a round-trip connection from $177 and Southwest from $177.

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 88 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be March, April and May. The cheapest month to fly is August.

Reviews of the 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.
8.0
SouthwestOverall score based on 4246 reviews
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

Terrible. Delayed 7 hours, and cancelled the flight, leaving me stranded and out of pocket $500 for an alternative last minute flight

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Our flight was understandably diverted to a small regional airport in Laramie, Wyoming due to weather conditions, which I fully recognize and appreciate. However, the low rating stems from the experience that followed: passengers remained on board for over an hour without the option to deplane and stretch, despite the aircraft being stationary. Although the pilot opened the cabin door, only he was permitted to exit. Meanwhile, passengers grew increasingly uncomfortable as warm summer air entered the cabin through the open door, and being in the second row meant we were impacted immediately. While the flight attendants made efforts to keep everyone at ease, I believe allowing passengers to deplane briefly, given the extended delay, would have significantly improved the overall experience.

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

Not a great experience. We paid for the upgrade for premium economy seats and seated ourselves in very comfortable seats. Someone came along with the same seat on their boarding pass. The aircraft had been changed and as a result we were booted out and sent further back to small uncomfortable seats. After complaining we were moved to emergency row seats, which gave us more leg room but the seats don’t recline. For people in our 70’s we found having to sit upright from California to NJ very uncomfortable. Not sure why they chose to move senior citizens instead of the two people that were allowed to take the more comfortable seats. Not happy.

I liked the choice of lemon ginger tea. I think stewardesses can be more considerate of older people needs.

We had to turn around and head back to Manchester. Problem with a plane engine.

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

The ticketing agents were rude but then we had a great gate agent very nice we had to ride a buss out to where the plane was parked but it was in some back corner of the airport when we got to the plane the captain who was great btw was cleaning the plane because the same rude ticketing agent told them they we not contracted to vacuum the plane. The ride to las Vegas was fine We had a connecting flight to Dallas. The flight was fine but when we arrived in Dallas everyone who flew on any frontier airlines the picked up bags from baggage claim D15 had to wait over a hour for their bags to start we arrived at 11:30pm ish to the gate we didn't leave the baggage clamed till 12:50 am very not happy and i used to fly frontier 4 times a week for work in Denver i will not be using them again

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

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