$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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — IAD
Sep 4 — Sep 111
Round-trip
1 adult, Economy
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Find cheap flights from Cleveland to Annapolis with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Annapolis are usually found in October or April, booked 40 days in advance, depart on a Friday or Thursday and return on a Saturday
Cheap flight deals from Cleveland to Annapolis
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Cheapest flights from Cleveland to AnnapolisExplore 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 August 5, 2026.
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 August 5, 2026.
This Southwest deal was found by Cheapflights users on 7/31. 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.
Sat 9/55:40 am -
Nonstop1h 20m
Sun 9/69:30 pm -
Nonstop1h 15m
Deal found 7/31![Southwest logo]()
$117
This Southwest deal was found by Cheapflights users on 7/31. 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.
Sat 9/53:15 pm -
Nonstop1h 20m
Tue 9/83:40 pm -
Nonstop1h 20m
Deal found 7/31![Southwest logo]()
$134
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:25 am -
1 stop10h 11m
Mon 11/28:00 am -
1 stop5h 29m
Deal found 7/30![Frontier logo]()
$135
This Expedia deal was found by Cheapflights users on 8/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am -
1 stop15h 30m
Wed 9/26:24 am -
1 stop6h 08m
Deal found 8/1![Frontier logo]()
$142
This Frontier deal was found by Cheapflights users on 7/31. 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.
Mon 9/149:59 pm -
1 stop10h 32m
Mon 9/219:32 pm -
1 stop11h 35m
Deal found 7/31![Frontier logo]()
$143
This Southwest deal was found by Cheapflights users on 8/2. 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.
Thu 9/35:40 am -
Nonstop1h 20m
Sun 9/63:05 pm -
2 stops6h 25m
Deal found 8/2![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 8/4. 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 9/111:40 am -
Nonstop1h 15m
Tue 9/83:40 pm -
Nonstop1h 20m
Deal found 8/4![Southwest logo]()
$151
This Delta deal was found by Cheapflights users on 8/3. 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 10/178:10 am -
1 stop3h 24m
Tue 10/2010:57 am -
1 stop4h 09m
Deal found 8/3![Delta logo]()
$171
This Delta deal was found by Cheapflights users on 8/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:18 am -
1 stop3h 10m
Tue 9/89:40 am -
1 stop4h 00m
Deal found 8/1![Delta logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/213:45 pm -
1 stop8h 25m
Fri 9/259:04 pm -
1 stop15h 00m
Deal found 7/31![Frontier logo]()
$172
This Frontier deal was found by Cheapflights users on 8/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/19:27 pm -
1 stop10h 37m
Wed 9/211:05 am -
1 stop9h 37m
Deal found 8/1![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/213:45 pm -
1 stop8h 25m
Wed 9/237:50 am -
1 stop13h 02m
Deal found 7/31![Frontier logo]()
$175
Best flights from Cleveland to AnnapolisDiscover carefully curated flight deals from Cleveland to Annapolis that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 5, 2026.
Discover carefully curated flight deals from Cleveland to Annapolis that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 5, 2026.
This Southwest deal was found by Cheapflights users on 7/31. 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.
Sat 9/53:15 pm -
Nonstop1h 20m
Sun 9/63:05 pm -
2 stops6h 25m
Deal found 7/31![Southwest logo]()
$132
This Delta deal was found by Cheapflights users on 8/2. 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.
Wed 9/210:24 am -
1 stop6h 14m
Wed 9/306:10 am -
1 stop3h 16m
Deal found 8/2![Delta logo]()
$171
This Frontier deal was found by Cheapflights users on 8/4. 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.
Fri 8/286:45 am -
1 stop10h 58m
Sun 8/301:20 pm -
1 stop10h 09m
Deal found 8/4![Frontier logo]()
$172
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Fri 10/1610:41 am -
Nonstop1h 14m
Mon 10/1910:33 pm -
Nonstop1h 26m
Deal found 7/31![United Airlines logo]()
$202
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:20 am -
1 stop5h 26m
Fri 9/254:35 pm -
1 stop6h 57m
Deal found 7/31![JetBlue logo]()
$253
This Southwest deal was found by Cheapflights users on 8/4. 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.
Fri 9/115:25 pm -
1 stop5h 25m
Mon 9/148:35 pm -
Nonstop1h 25m
Deal found 8/4![Southwest logo]()
$144
This Southwest deal was found by Cheapflights users on 8/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
Nonstop1h 20m
Sat 10/2410:35 am -
Nonstop1h 20m
Deal found 8/1![Southwest logo]()
$151
This Delta deal was found by Cheapflights users on 8/3. 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 9/122:20 pm -
1 stop3h 09m
Mon 9/147:25 pm -
1 stop4h 29m
Deal found 8/3![Delta logo]()
$171
This Southwest deal was found by Cheapflights users on 7/31. 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.
Mon 9/146:05 pm -
1 stop4h 35m
Mon 9/218:35 pm -
Nonstop1h 25m
Deal found 7/31![Southwest logo]()
$161
This Expedia deal was found by Cheapflights users on 8/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:45 am -
1 stop10h 58m
Thu 8/2011:09 am -
1 stop9h 33m
Deal found 8/4![Frontier logo]()
$210
This United Airlines deal was found by Cheapflights users on 8/3. 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 1/136:00 am -
Nonstop1h 35m
Thu 1/218:15 am -
Nonstop1h 12m
Deal found 8/3![United Airlines logo]()
$221
This Southwest deal was found by Cheapflights users on 7/31. 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 8/268:45 am -
2 stops7h 40m
Mon 9/286:35 am -
1 stop6h 35m
Deal found 7/31![Southwest logo]()
$176
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Sat 10/177:57 pm -
Nonstop1h 30m
Tue 10/2010:33 pm -
Nonstop1h 26m
Deal found 8/4![United Airlines logo]()
$221
This Delta deal was found by Cheapflights users on 8/3. 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.
Fri 9/256:30 am -
1 stop3h 51m
Mon 9/286:10 am -
1 stop3h 16m
Deal found 8/3![Delta logo]()
$222
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:50 am -
1 stop6h 23m
Sun 9/63:20 pm -
1 stop8h 35m
Deal found 7/31![JetBlue logo]()
$255
This Delta deal was found by Cheapflights users on 8/4. 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.
Fri 10/167:55 pm -
1 stop3h 12m
Tue 10/209:32 am -
1 stop4h 07m
Deal found 8/4![Delta logo]()
$222
This JetBlue deal was found by Cheapflights users on 8/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:05 am -
1 stop4h 45m
Mon 10/263:55 pm -
1 stop5h 35m
Deal found 8/4![JetBlue logo]()
$263
This Delta deal was found by Cheapflights users on 8/2. 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.
Fri 10/27:40 pm -
1 stop3h 22m
Mon 10/55:35 pm -
1 stop6h 19m
Deal found 8/2![Delta logo]()
$222
This Southwest deal was found by Cheapflights users on 8/3. 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 9/1511:40 am -
Nonstop1h 15m
Thu 9/178:35 pm -
Nonstop1h 25m
Deal found 8/3![Southwest logo]()
$202
This JetBlue deal was found by Cheapflights users on 8/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2911:35 am -
1 stop6h 59m
Sat 10/32:00 pm -
1 stop6h 11m
Deal found 8/4![JetBlue logo]()
$263
This United Airlines deal was found by Cheapflights users on 8/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:41 am -
Nonstop1h 14m
Mon 10/268:15 am -
Nonstop1h 23m
Deal found 8/1![United Airlines logo]()
$272
This Delta deal was found by Cheapflights users on 8/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:55 pm -
1 stop3h 12m
Sun 10/259:32 am -
1 stop4h 07m
Deal found 8/1![Delta logo]()
$225
This United Airlines deal was found by Cheapflights users on 8/4. 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 11/510:34 am -
Nonstop1h 21m
Sun 11/88:15 am -
Nonstop1h 23m
Deal found 8/4![United Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 8/3. 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.
Sat 9/1210:35 am -
2 stops7h 50m
Mon 9/1410:25 am -
2 stops8h 15m
Deal found 8/3![Southwest logo]()
$232
This United Airlines deal was found by Cheapflights users on 8/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:57 pm -
Nonstop1h 19m
Sun 10/258:15 am -
Nonstop1h 23m
Deal found 8/1![United Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 8/4. 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.
Fri 8/282:20 pm -
1 stop4h 25m
Sun 8/306:10 am -
1 stop3h 25m
Deal found 8/4![Delta logo]()
$276
This Southwest deal was found by Cheapflights users on 7/31. 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.
Fri 10/94:50 pm -
1 stop7h 05m
Mon 10/1210:25 pm -
Nonstop1h 20m
Deal found 7/31![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 7/31. 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.
Fri 9/46:40 am -
2 stops7h 55m
Sun 9/63:05 pm -
2 stops6h 25m
Deal found 7/31![Southwest logo]()
$265
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Fri 11/610:34 am -
Nonstop1h 21m
Sun 11/88:15 am -
Nonstop1h 23m
Deal found 8/4![United Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 8/3. 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.
Fri 9/45:25 pm -
1 stop5h 25m
Mon 9/76:35 am -
2 stops8h 35m
Deal found 8/3![Southwest logo]()
$278
Last-minute flights from Cleveland to AnnapolisDiscover last-minute flight deals from Cleveland to Annapolis. Data last updated August 5, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Annapolis. Data last updated August 5, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 8/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:45 am -
1 stop5h 39m
Thu 8/277:52 pm -
1 stop24h 50m
Deal found 8/2![Frontier logo]()
$152
This Expedia deal was found by Cheapflights users on 8/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:45 am -
1 stop10h 58m
Tue 9/811:30 am -
1 stop8h 52m
Deal found 8/1![Frontier logo]()
$142
This Southwest deal was found by Cheapflights users on 8/4. 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 9/111:40 am -
Nonstop1h 15m
Tue 9/83:40 pm -
Nonstop1h 20m
Deal found 8/4![Southwest logo]()
$151
This Delta deal was found by Cheapflights users on 8/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:18 am -
1 stop3h 10m
Tue 9/89:40 am -
1 stop4h 00m
Deal found 8/1![Delta logo]()
$171
This Frontier deal was found by Cheapflights users on 8/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:45 am -
1 stop10h 29m
Thu 9/36:20 am -
1 stop5h 35m
Deal found 8/1![Frontier logo]()
$174
This Southwest deal was found by Cheapflights users on 8/2. 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.
Thu 9/35:40 am -
Nonstop1h 20m
Sun 9/63:05 pm -
2 stops6h 25m
Deal found 8/2![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 8/3. 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.
Sat 9/55:40 am -
Nonstop1h 20m
Sun 9/69:30 pm -
Nonstop1h 15m
Deal found 8/3![Southwest logo]()
$117
This Southwest deal was found by Cheapflights users on 7/31. 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.
Sat 9/53:15 pm -
Nonstop1h 20m
Tue 9/83:40 pm -
Nonstop1h 20m
Deal found 7/31![Southwest logo]()
$134
This Southwest deal was found by Cheapflights users on 7/31. 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.
Sat 9/51:55 pm -
1 stop5h 20m
Mon 9/710:55 am -
Nonstop1h 20m
Deal found 7/31![Southwest logo]()
$144
This Delta deal was found by Cheapflights users on 8/3. 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 9/510:24 am -
1 stop6h 14m
Mon 9/76:10 am -
1 stop3h 26m
Deal found 8/3![Delta logo]()
$171
This Frontier deal was found by Cheapflights users on 7/31. 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.
Mon 9/149:59 pm -
1 stop10h 32m
Mon 9/219:32 pm -
1 stop11h 35m
Deal found 7/31![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/213:45 pm -
1 stop8h 25m
Fri 9/259:04 pm -
1 stop15h 00m
Deal found 7/31![Frontier logo]()
$172
One-way flights from Cleveland to AnnapolisSearch for one-way flight options from Cleveland to Annapolis. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
Search for one-way flight options from Cleveland to Annapolis. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1611:40 am -
Nonstop1h 15m
Deal found 7/30![Southwest logo]()
$59
This Southwest deal was found by Cheapflights users on 7/31. 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.
Fri 10/301:35 pm -
1 stop4h 00m
Deal found 7/31![Southwest logo]()
$69
This Frontier deal was found by Cheapflights users on 8/3. 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.
Tue 9/19:27 pm -
1 stop10h 37m
Deal found 8/3![Frontier logo]()
$71
This Frontier deal was found by Cheapflights users on 7/31. 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.
Tue 9/16:45 am -
1 stop5h 39m
Deal found 7/31![Frontier logo]()
$71
This Southwest deal was found by Cheapflights users on 8/4. 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 9/111:40 am -
Nonstop1h 15m
Deal found 8/4![Southwest logo]()
$76
This Frontier deal was found by Cheapflights users on 8/4. 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.
Mon 9/79:47 pm -
1 stop12h 20m
Deal found 8/4![Frontier logo]()
$77
This Frontier deal was found by Cheapflights users on 7/31. 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.
Sat 10/37:00 am -
1 stop9h 46m
Deal found 7/31![Frontier logo]()
$77
This Delta deal was found by Cheapflights users on 8/4. 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.
Sun 9/66:43 am -
1 stop4h 49m
Deal found 8/4![Delta logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/295:15 pm -
1 stop29h 37m
Deal found 7/31![Frontier logo]()
$81
This American Airlines deal was found by Cheapflights users on 8/3. 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.
Tue 9/292:41 pm -
1 stop4h 52m
Deal found 8/3![American Airlines logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 8/185:15 pm -
1 stop23h 59m
Deal found 8/2![Frontier logo]()
$82
This Frontier deal was found by Cheapflights users on 7/31. 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.
Fri 10/23:45 pm -
1 stop7h 19m
Deal found 7/31![Frontier logo]()
$82
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 August 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (Southwest) |
One-way from | $59 (Southwest) |
Popular in | June |
Cheapest in | October |
Average price | $249 |
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 August 5, 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
Cheapest round-trip
ClevelandBaltimore
CLE - BWI
CLEBWI
Cleveland Hopkins Intl
Sat 9/5
3:15 pm-4:35 pm
Nonstop1h 20m
Baltimore/Washington
Sun 9/6
3:05 pm-9:30 pm
2 stops6h 25m
$132
ClevelandBaltimore
CLE - BWI
CLEBWI
Cleveland Hopkins Intl
Fri 9/11
5:25 pm-10:50 pm
1 stop5h 25m
Baltimore/Washington
Mon 9/14
8:35 pm-10:00 pm
Nonstop1h 25m
$144
ClevelandBaltimore
CLE - BWI
CLEBWI
Cleveland Hopkins Intl
Thu 10/22
6:00 am-7:20 am
Nonstop1h 20m
Baltimore/Washington
Sat 10/24
10:35 am-11:55 am
Nonstop1h 20m
$151
ClevelandBaltimore
CLE - BWI
CLEBWI
Cleveland Hopkins Intl
Mon 9/14
6:05 pm-10:40 pm
1 stop4h 35m
Baltimore/Washington
Mon 9/21
8:35 pm-10:00 pm
Nonstop1h 25m
$161
ClevelandWashington, D.C.
CLE - IAD
CLEIAD
Cleveland Hopkins Intl
Wed 9/2
10:24 am-4:38 pm
1 stop6h 14m
Washington, D.C. Dulles Intl
Wed 9/30
6:10 am-9:26 am
1 stop3h 16m
$171
ClevelandWashington, D.C.
CLE - DCA
CLEDCA
Cleveland Hopkins Intl
Sat 9/12
2:20 pm-5:29 pm
1 stop3h 09m
Washington, D.C. Reagan-National
Mon 9/14
7:25 pm-11:54 pm
1 stop4h 29m
$171
ClevelandBaltimore
CLE - BWI
CLEBWI
Cleveland Hopkins Intl
Fri 8/28
6:45 am-5:43 pm
1 stop10h 58m
Baltimore/Washington
Sun 8/30
1:20 pm-11:29 pm
1 stop10h 09m
$172
ClevelandBaltimore
CLE - BWI
CLEBWI
Cleveland Hopkins Intl
Wed 8/26
8:45 am-4:25 pm
2 stops7h 40m
Baltimore/Washington
Mon 9/28
6:35 am-1:10 pm
1 stop6h 35m
$176
ClevelandWashington, D.C.
CLE - IAD
CLEIAD
Cleveland Hopkins Intl
Fri 10/16
10:41 am-11:55 am
Nonstop1h 14m
Washington, D.C. Dulles Intl
Mon 10/19
10:33 pm-11:59 pm
Nonstop1h 26m
$202
ClevelandBaltimore
CLE - BWI
CLEBWI
Cleveland Hopkins Intl
Tue 9/15
11:40 am-12:55 pm
Nonstop1h 15m
Baltimore/Washington
Thu 9/17
8:35 pm-10:00 pm
Nonstop1h 25m
$202
Showing 1-10 of 60 resultsSorted by cheapest first
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.
CLE-BWI
CLE-IAD
CLE-DCA
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
CLE-AP9
CLE-BWI
CLE-IAD
CLE-DCA
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 August 5, 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.
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 August 5, 2026.
The most flights from CLE to AP9 are scheduled on a Monday (18 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?
Airfare is below average for this route at the moment.
Cleveland to Annapolis flights typically cost between $194 and $314 in September.The cheapest round-trip price found within the last 5 days was $117 on Southwest (Sep 5-Sep 6).
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 1, 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.
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 August 5, 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.
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
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.
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Cleveland and Annapolis flights
Browse other Cleveland and Annapolis flight options. Last updated on August 5, 2026.
Other flights from Cleveland
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Popular flight searches
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Cleveland to Annapolis flights
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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 August 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$113 | Average$293 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$117 | Average$308 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$123 | Average$191 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$377 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$159 | Average$307 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$166 | Average$312 | FlexibilityNo cancel fee | On-timeN/A |