$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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — IAD
Aug 28 — Sep 41
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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Best
Last-minute
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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 July 29, 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 July 29, 2026.
This Southwest deal was found by Cheapflights users on 7/27. 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 8/183:20 pm
CLE
- BWI
Nonstop1h 20m
Southwest
Wed 8/1910:50 am
BWI
- CLE
Nonstop1h 20m
Southwest
Deal found 7/27![Southwest logo]()
$117
This Southwest deal was found by Cheapflights users on 7/28. 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 9/113:50 pm
CLE
- BWI
Nonstop1h 20m
Southwest
Mon 9/148:35 pm
BWI
- CLE
Nonstop1h 25m
Southwest
Deal found 7/28![Southwest logo]()
$122
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/104:07 pm
CLE
- BWI
1 stop5h 28m
Delta
Wed 10/149:46 am
BWI
- CLE
1 stop3h 53m
Delta
Deal found 7/27![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 7/27. 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.
Thu 9/31:15 pm
CLE
- BWI
1 stop9h 25m
Southwest
Wed 9/910:55 am
BWI
- CLE
2 stops6h 50m
Southwest
Deal found 7/27![Southwest logo]()
$148
This Southwest deal was found by Cheapflights users on 7/28. 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 8/298:55 am
CLE
- BWI
2 stops7h 05m
Southwest
Sun 9/63:05 pm
BWI
- CLE
2 stops6h 25m
Southwest
Deal found 7/28![Southwest logo]()
$152
This Southwest deal was found by Cheapflights users on 7/27. 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.
Sat 12/128:35 am
CLE
- BWI
2 stops6h 10m
Southwest
Mon 12/148:15 am
BWI
- CLE
2 stops10h 05m
Southwest
Deal found 7/27![Southwest logo]()
$153
This Southwest deal was found by Cheapflights users on 7/25. 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 10/84:50 pm
CLE
- BWI
1 stop7h 05m
Southwest
Mon 10/126:35 am
BWI
- CLE
1 stop6h 20m
Southwest
Deal found 7/25![Southwest logo]()
$154
This American Airlines deal was found by Cheapflights users on 7/26. 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 9/84:54 pm
CLE
- BWI
1 stop4h 58m
American Airlines
Thu 9/107:09 pm
BWI
- CLE
1 stop4h 14m
American Airlines
Deal found 7/26![American Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/196:45 am
CLE
- IAD
1 stop10h 29m
Frontier
Sat 8/227:00 am
IAD
- CLE
1 stop15h 31m
Frontier
Deal found 7/28![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
Mon 9/143:45 pm
CLE
- IAD
1 stop8h 25m
Frontier
Wed 9/167:50 am
IAD
- CLE
1 stop13h 02m
Frontier
Deal found 7/27![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 9/36:45 am
CLE
- IAD
1 stop10h 29m
Frontier
Tue 9/86:09 pm
IAD
- CLE
1 stop25h 57m
Frontier
Deal found 7/26![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 10/83:40 pm
CLE
- IAD
1 stop8h 48m
Frontier
Thu 10/159:16 pm
IAD
- CLE
1 stop14h 04m
Frontier
Deal found 7/26![Frontier logo]()
$181
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 July 29, 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 July 29, 2026.
This Southwest deal was found by Cheapflights users on 7/28. 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 8/196:00 am
CLE
- BWI
Nonstop1h 20m
Southwest
Sat 8/227:35 pm
BWI
- CLE
Nonstop1h 20m
Southwest
Deal found 7/28![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 7/25. 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 10/176:10 am
CLE
- BWI
1 stop5h 42m
Delta
Tue 10/206:10 am
BWI
- CLE
1 stop3h 15m
Delta
Deal found 7/25![Delta logo]()
$147
This United Airlines deal was found by Cheapflights users on 7/25. 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
CLE
- IAD
Nonstop1h 30m
United Airlines
Tue 10/2010:33 pm
IAD
- CLE
Nonstop1h 26m
United Airlines
Deal found 7/25![United Airlines logo]()
$187
This Southwest deal was found by Cheapflights users on 7/24. 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 8/183:20 pm
CLE
- BWI
Nonstop1h 20m
Southwest
Wed 8/1910:50 am
BWI
- CLE
Nonstop1h 20m
Southwest
Deal found 7/24![Southwest logo]()
$117
This JetBlue deal was found by Cheapflights users on 7/28. 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.
Wed 9/169:20 am
CLE
- DCA
1 stop5h 26m
JetBlue
Sun 9/204:35 pm
DCA
- CLE
1 stop6h 57m
JetBlue
Deal found 7/28![JetBlue logo]()
$253
This American Airlines deal was found by Cheapflights users on 7/28. 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.
Fri 9/45:15 am
CLE
- DCA
1 stop5h 44m
American Airlines
Mon 9/712:27 pm
DCA
- CLE
Nonstop1h 33m
American Airlines
Deal found 7/28![American Airlines logo]()
$263
This Southwest deal was found by Cheapflights users on 7/26. 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 9/911:40 am
CLE
- BWI
Nonstop1h 15m
Southwest
Wed 9/1610:35 am
BWI
- CLE
1 stop4h 10m
Southwest
Deal found 7/26![Southwest logo]()
$127
This Southwest deal was found by Cheapflights users on 7/26. 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 9/173:50 pm
CLE
- BWI
Nonstop1h 20m
Southwest
Sat 9/198:15 am
BWI
- CLE
2 stops8h 30m
Southwest
Deal found 7/26![Southwest logo]()
$132
This United Airlines deal was found by Cheapflights users on 7/28. 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 10/2210:41 am
CLE
- IAD
Nonstop1h 14m
United Airlines
Mon 10/268:15 am
IAD
- CLE
Nonstop1h 23m
United Airlines
Deal found 7/28![United Airlines logo]()
$187
This Delta deal was found by Cheapflights users on 7/28. 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 10/110:27 am
CLE
- DCA
1 stop6h 11m
Delta
Mon 10/55:35 pm
DCA
- CLE
1 stop6h 19m
Delta
Deal found 7/28![Delta logo]()
$188
This Southwest deal was found by Cheapflights users on 7/25. 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 8/226:10 am
CLE
- BWI
2 stops8h 15m
Southwest
Sat 8/2910:45 am
BWI
- CLE
2 stops8h 05m
Southwest
Deal found 7/25![Southwest logo]()
$147
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:40 pm
CLE
- DCA
1 stop3h 22m
Delta
Sat 9/199:40 am
DCA
- CLE
1 stop4h 00m
Delta
Deal found 7/27![Delta logo]()
$188
This United Airlines deal was found by Cheapflights users on 7/25. 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 9/118:04 pm
CLE
- IAD
Nonstop1h 19m
United Airlines
Mon 9/1410:22 pm
IAD
- CLE
Nonstop1h 22m
United Airlines
Deal found 7/25![United Airlines logo]()
$192
This JetBlue deal was found by Cheapflights users on 7/24. 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 8/1810:07 am
CLE
- DCA
1 stop4h 18m
JetBlue
Wed 8/198:49 am
DCA
- CLE
1 stop6h 56m
JetBlue
Deal found 7/24![JetBlue logo]()
$253
This Delta deal was found by Cheapflights users on 7/28. 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 10/166:10 am
CLE
- IAD
1 stop4h 02m
Delta
Tue 10/206:05 am
IAD
- CLE
1 stop3h 20m
Delta
Deal found 7/28![Delta logo]()
$215
This JetBlue deal was found by Cheapflights users on 7/24. 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.
Fri 10/27:00 am
CLE
- DCA
1 stop7h 58m
JetBlue
Mon 10/512:25 pm
DCA
- CLE
1 stop7h 46m
JetBlue
Deal found 7/24![JetBlue logo]()
$253
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:55 pm
CLE
- DCA
1 stop3h 12m
Delta
Tue 10/2012:27 pm
DCA
- CLE
1 stop6h 09m
Delta
Deal found 7/27![Delta logo]()
$215
This JetBlue deal was found by Cheapflights users on 7/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:20 am
CLE
- DCA
1 stop8h 00m
JetBlue
Fri 9/254:35 pm
DCA
- CLE
1 stop6h 57m
JetBlue
Deal found 7/27![JetBlue logo]()
$253
This United Airlines deal was found by Cheapflights users on 7/28. 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 8/2210:37 am
CLE
- IAD
Nonstop1h 15m
United Airlines
Sun 8/2312:49 pm
IAD
- CLE
Nonstop1h 21m
United Airlines
Deal found 7/28![United Airlines logo]()
$258
This Delta deal was found by Cheapflights users on 7/26. 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 9/38:18 am
CLE
- DCA
1 stop3h 10m
Delta
Mon 9/76:10 am
DCA
- CLE
1 stop3h 26m
Delta
Deal found 7/26![Delta logo]()
$258
This United Airlines deal was found by Cheapflights users on 7/28. 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 11/276:00 am
CLE
- IAD
Nonstop1h 20m
United Airlines
Sun 11/298:15 am
IAD
- CLE
Nonstop1h 23m
United Airlines
Deal found 7/28![United Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 7/28. 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 9/36:43 am
CLE
- IAD
1 stop3h 40m
Delta
Mon 9/76:10 am
IAD
- CLE
1 stop3h 26m
Delta
Deal found 7/28![Delta logo]()
$259
This United Airlines deal was found by Cheapflights users on 7/25. 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
CLE
- IAD
Nonstop1h 21m
United Airlines
Sun 11/88:15 am
IAD
- CLE
Nonstop1h 23m
United Airlines
Deal found 7/25![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 7/26. 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 9/47:43 pm
CLE
- IAD
1 stop3h 43m
Delta
Mon 9/76:10 am
IAD
- CLE
1 stop3h 26m
Delta
Deal found 7/26![Delta logo]()
$273
This United Airlines deal was found by Cheapflights users on 7/24. 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
CLE
- IAD
Nonstop1h 21m
United Airlines
Sun 11/88:15 am
IAD
- CLE
Nonstop1h 23m
United Airlines
Deal found 7/24![United Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 7/24. 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 8/126:00 am
CLE
- IAD
Nonstop1h 14m
United Airlines
Wed 8/1912:49 pm
IAD
- CLE
Nonstop1h 21m
United Airlines
Deal found 7/24![United Airlines logo]()
$344
Last-minute flights from Cleveland to AnnapolisDiscover last-minute flight deals from Cleveland to Annapolis. Data last updated July 29, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Annapolis. Data last updated July 29, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 7/25. 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 8/1510:37 am
CLE
- IAD
Nonstop1h 15m
United Airlines
Mon 8/1712:49 pm
IAD
- CLE
Nonstop1h 21m
United Airlines
Deal found 7/25![United Airlines logo]()
$188
This Southwest deal was found by Cheapflights users on 7/27. 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 8/183:20 pm
CLE
- BWI
Nonstop1h 20m
Southwest
Wed 8/1910:50 am
BWI
- CLE
Nonstop1h 20m
Southwest
Deal found 7/27![Southwest logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/196:45 am
CLE
- IAD
1 stop10h 29m
Frontier
Sat 8/227:00 am
IAD
- CLE
1 stop15h 31m
Frontier
Deal found 7/28![Frontier logo]()
$176
This United Airlines deal was found by Cheapflights users on 7/27. 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.
Thu 8/207:54 pm
CLE
- IAD
Nonstop1h 19m
United Airlines
Sat 8/228:20 am
IAD
- CLE
Nonstop1h 21m
United Airlines
Deal found 7/27![United Airlines logo]()
$187
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Thu 8/206:00 am
CLE
- DCA
Nonstop1h 25m
American Airlines
Sun 8/2310:45 am
DCA
- CLE
Nonstop1h 29m
American Airlines
Deal found 7/26![American Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/216:45 am
CLE
- BWI
1 stop5h 39m
Frontier
Sun 8/238:45 am
BWI
- CLE
1 stop27h 10m
Frontier
Deal found 7/28![Frontier logo]()
$179
This American Airlines deal was found by Cheapflights users on 7/28. 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.
Fri 8/217:54 pm
CLE
- DCA
Nonstop1h 36m
American Airlines
Mon 8/3110:16 pm
DCA
- CLE
Nonstop1h 30m
American Airlines
Deal found 7/28![American Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 8/245:15 pm
CLE
- IAD
1 stop5h 37m
Frontier
Mon 8/316:20 am
IAD
- CLE
1 stop5h 35m
Frontier
Deal found 7/26![Frontier logo]()
$181
This United Airlines deal was found by Cheapflights users on 7/27. 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.
Mon 8/2410:37 am
CLE
- IAD
Nonstop1h 15m
United Airlines
Mon 8/315:31 pm
IAD
- CLE
Nonstop1h 27m
United Airlines
Deal found 7/27![United Airlines logo]()
$185
This Southwest deal was found by Cheapflights users on 7/26. 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 8/2811:00 am
CLE
- BWI
Nonstop1h 20m
Southwest
Mon 8/3110:55 am
BWI
- CLE
Nonstop1h 20m
Southwest
Deal found 7/26![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 7/28. 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 8/293:15 pm
CLE
- BWI
Nonstop1h 20m
Southwest
Sun 9/69:30 pm
BWI
- CLE
Nonstop1h 15m
Southwest
Deal found 7/28![Southwest logo]()
$122
This Southwest deal was found by Cheapflights users on 7/28. 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 8/313:50 pm
CLE
- BWI
Nonstop1h 20m
Southwest
Tue 9/17:40 pm
BWI
- CLE
Nonstop1h 20m
Southwest
Deal found 7/28![Southwest logo]()
$187
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 July 29, 2026.
Search for one-way flight options from Cleveland to Annapolis. Find affordable one-way fares based on user searches. Data last updated July 29, 2026.
This Southwest deal was found by Cheapflights users on 7/28. 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 8/253:20 pm
CLE
- BWI
Nonstop1h 20m
Southwest
Deal found 7/28![Southwest logo]()
$59
This Southwest deal was found by Cheapflights users on 7/24. 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.
Sun 9/66:35 am
CLE
- BWI
Nonstop1h 20m
Southwest
Deal found 7/24![Southwest logo]()
$64
This Delta deal was found by Cheapflights users on 7/28. 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 8/258:18 am
CLE
- BWI
1 stop3h 24m
Delta
Deal found 7/28![Delta logo]()
$74
This Delta deal was found by Cheapflights users on 7/28. 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 10/307:55 pm
CLE
- BWI
1 stop3h 09m
Delta
Deal found 7/28![Delta logo]()
$79
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Fri 9/116:09 am
CLE
- BWI
1 stop3h 35m
American Airlines
Deal found 7/26![American Airlines logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Sun 8/305:15 pm
CLE
- IAD
1 stop5h 37m
Frontier
Deal found 7/29![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 7/28. 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
CLE
- IAD
1 stop23h 59m
Frontier
Deal found 7/28![Frontier logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/255:15 pm
CLE
- IAD
1 stop23h 59m
Frontier
Deal found 7/28![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 9/113:45 pm
CLE
- IAD
1 stop25h 33m
Frontier
Deal found 7/26![Frontier logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/216:45 am
CLE
- BWI
1 stop5h 39m
Frontier
Deal found 7/28![Frontier logo]()
$91
This Trip.com deal was found by Cheapflights users on 7/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:45 am
CLE
- IAD
1 stop16h 07m
Frontier
Deal found 7/29![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/276:45 am
CLE
- BWI
1 stop5h 39m
Frontier
Deal found 7/28![Frontier logo]()
$93
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 July 29, 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 | $304 |
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 July 29, 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
Wed 8/19
6:00 am-7:20 am
Nonstop1h 20m
Baltimore/Washington
Sat 8/22
7:35 pm-8:55 pm
Nonstop1h 20m
$117
ClevelandBaltimore
CLE - BWI
CLEBWI
Cleveland Hopkins Intl
Tue 8/18
3:20 pm-4:40 pm
Nonstop1h 20m
Baltimore/Washington
Wed 8/19
10:50 am-12:10 pm
Nonstop1h 20m
$117
ClevelandBaltimore
CLE - BWI
CLEBWI
Cleveland Hopkins Intl
Wed 9/9
11:40 am-12:55 pm
Nonstop1h 15m
Baltimore/Washington
Wed 9/16
10:35 am-2:45 pm
1 stop4h 10m
$127
ClevelandBaltimore
CLE - BWI
CLEBWI
Cleveland Hopkins Intl
Thu 9/17
3:50 pm-5:10 pm
Nonstop1h 20m
Baltimore/Washington
Sat 9/19
8:15 am-4:45 pm
2 stops8h 30m
$132
ClevelandBaltimore
CLE - BWI
CLEBWI
Cleveland Hopkins Intl
Sat 10/17
6:10 am-11:52 am
1 stop5h 42m
Baltimore/Washington
Tue 10/20
6:10 am-9:25 am
1 stop3h 15m
$147
ClevelandBaltimore
CLE - BWI
CLEBWI
Cleveland Hopkins Intl
Sat 8/22
6:10 am-2:25 pm
2 stops8h 15m
Baltimore/Washington
Sat 8/29
10:45 am-6:50 pm
2 stops8h 05m
$147
ClevelandWashington, D.C.
CLE - IAD
CLEIAD
Cleveland Hopkins Intl
Sat 10/17
7:57 pm-9:27 pm
Nonstop1h 30m
Washington, D.C. Dulles Intl
Tue 10/20
10:33 pm-11:59 pm
Nonstop1h 26m
$187
ClevelandWashington, D.C.
CLE - IAD
CLEIAD
Cleveland Hopkins Intl
Thu 10/22
10:41 am-11:55 am
Nonstop1h 14m
Washington, D.C. Dulles Intl
Mon 10/26
8:15 am-9:38 am
Nonstop1h 23m
$187
ClevelandWashington, D.C.
CLE - DCA
CLEDCA
Cleveland Hopkins Intl
Thu 10/1
10:27 am-4:38 pm
1 stop6h 11m
Washington, D.C. Reagan-National
Mon 10/5
5:35 pm-11:54 pm
1 stop6h 19m
$188
ClevelandWashington, D.C.
CLE - DCA
CLEDCA
Cleveland Hopkins Intl
Wed 9/16
7:40 pm-11:02 pm
1 stop3h 22m
Washington, D.C. Reagan-National
Sat 9/19
9:40 am-1:40 pm
1 stop4h 00m
$188
Showing 1-10 of 56 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 July 29, 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 July 29, 2026.
The most flights from CLE to AP9 are scheduled on a Monday (17 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 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 $198 and $304 in August.The cheapest round-trip price found within the last 5 days was $117 on Southwest (Aug 18-Aug 19).
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 July 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.
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 July 29, 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.
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
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 July 29, 2026.
Other flights from Cleveland
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Popular flight searches
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Top 5 airlines flying from Cleveland to Annapolis
Discover the top 5 airlines that operate flights from Cleveland to Annapolis. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$113 | Average$293 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$117 | Average$305 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$123 | Average$191 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$159 | Average$308 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$185 | Average$379 | FlexibilityNo cancel fee | On-time69% |