$57+ Cheap flights from Cleveland (CLE) to Annapolis, MD
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — IAD
Oct 17 — Oct 241
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 49 days in advance, depart on a Friday or Thursday and return on a Thursday
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 September 17, 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 September 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/169:59 pm -
1 stop10h 21m
Mon 10/199:52 pm -
1 stop11h 05m
Deal found 9/13![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/157:00 am -
1 stop9h 47m
Mon 10/196:24 am -
1 stop5h 45m
Deal found 9/13![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/37:00 am -
1 stop9h 46m
Mon 10/56:00 am -
1 stop6h 04m
Deal found 9/12![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/136:00 am -
1 stop8h 20m
Tue 10/207:05 pm -
1 stop13h 52m
Deal found 9/13![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/99:59 pm -
1 stop10h 21m
Mon 10/129:52 pm -
1 stop11h 05m
Deal found 9/16![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/203:46 pm -
1 stop8h 48m
Thu 10/225:40 am -
1 stop6h 29m
Deal found 9/14![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/213:46 pm -
1 stop8h 48m
Sat 10/245:40 am -
1 stop15h 12m
Deal found 9/12![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/103:46 pm -
1 stop8h 36m
Sat 11/146:24 am -
1 stop7h 10m
Deal found 9/14![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/63:45 pm -
1 stop17h 40m
Tue 10/139:12 pm -
1 stop23h 40m
Deal found 9/13![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/129:59 pm -
1 stop10h 21m
Mon 10/199:52 pm -
1 stop11h 05m
Deal found 9/13![Frontier logo]()
$142
This Expedia deal was found by Cheapflights users on 9/15. 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 10/66:00 am -
1 stop8h 11m
Wed 10/79:27 am -
1 stop15h 03m
Deal found 9/15![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/239:59 pm -
1 stop10h 21m
Mon 10/269:52 pm -
1 stop11h 14m
Deal found 9/14![Frontier logo]()
$146
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 September 17, 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 September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/13. 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 10/1310:10 am -
Nonstop1h 15m
Tue 10/203:25 pm -
Nonstop1h 20m
Deal found 9/13![Southwest logo]()
$224
This United Airlines deal was found by Cheapflights users on 9/15. 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 11/53:10 pm -
Nonstop1h 21m
Mon 11/98:15 am -
Nonstop1h 23m
Deal found 9/15![United Airlines logo]()
$241
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/165:25 pm -
1 stop6h 34m
Sun 10/2510:04 pm -
Nonstop1h 35m
Deal found 9/16![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 9/14. 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 3/610:10 am -
1 stop6h 20m
Wed 3/1011:05 am -
1 stop4h 04m
Deal found 9/14![Delta logo]()
$319
This JetBlue deal was found by Cheapflights users on 9/16. 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 9/16![JetBlue logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/163:46 pm -
2 stops20h 18m
Sun 10/257:00 am -
1 stop9h 15m
Deal found 9/16![Frontier logo]()
$504
This Southwest deal was found by Cheapflights users on 9/16. 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 12/23:50 pm -
Nonstop1h 20m
Fri 12/46:15 am -
1 stop6h 50m
Deal found 9/16![Southwest logo]()
$274
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/910:41 am -
Nonstop1h 14m
Mon 10/128:15 am -
Nonstop1h 20m
Deal found 9/16![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 9/16. 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 1/115:35 am -
Nonstop1h 30m
Thu 1/1410:45 am -
Nonstop1h 25m
Deal found 9/16![Southwest logo]()
$285
This Delta deal was found by Cheapflights users on 9/13. 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 12/157:50 pm -
1 stop3h 40m
Sun 1/1010:00 am -
1 stop5h 09m
Deal found 9/13![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/16. 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 12/163:10 pm -
Nonstop1h 21m
Sun 1/1010:10 pm -
Nonstop1h 11m
Deal found 9/16![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 9/15. 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 10/305:50 pm -
Nonstop1h 20m
Mon 11/26:55 pm -
Nonstop1h 20m
Deal found 9/15![Southwest logo]()
$303
This United Airlines deal was found by Cheapflights users on 9/15. 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 12/27:50 pm -
Nonstop1h 21m
Wed 3/318:15 am -
1 stop4h 28m
Deal found 9/15![United Airlines logo]()
$328
This Southwest deal was found by Cheapflights users on 9/14. 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 12/46:05 am -
2 stops6h 40m
Mon 12/72:30 pm -
2 stops6h 40m
Deal found 9/14![Southwest logo]()
$318
This United Airlines deal was found by Cheapflights users on 9/16. 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 9/16![United Airlines logo]()
$340
This Southwest deal was found by Cheapflights users on 9/16. 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 11/73:30 pm -
Nonstop1h 20m
Sun 11/86:40 am -
1 stop6h 05m
Deal found 9/16![Southwest logo]()
$321
This Delta deal was found by Cheapflights users on 9/16. 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 12/1710:45 am -
1 stop5h 54m
Sun 1/103:05 pm -
2 stops7h 36m
Deal found 9/16![Delta logo]()
$464
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/176:00 am -
Nonstop1h 14m
Mon 10/198:15 am -
Nonstop1h 20m
Deal found 9/16![United Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 9/15. 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 10/2312:40 pm -
Nonstop1h 15m
Fri 10/233:55 pm -
1 stop6h 35m
Deal found 9/15![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 9/14. 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 10/154:50 pm -
2 stops8h 00m
Sat 10/176:30 am -
1 stop4h 10m
Deal found 9/14![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 9/14. 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 3/87:51 pm -
Nonstop1h 26m
Sat 3/135:15 pm -
Nonstop1h 21m
Deal found 9/14![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 9/14. 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 10/38:28 am -
2 stops6h 27m
Mon 10/56:10 am -
1 stop3h 16m
Deal found 9/14![Delta logo]()
$493
This United Airlines deal was found by Cheapflights users on 9/14. 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 3/56:00 am -
Nonstop1h 35m
Fri 3/1210:10 pm -
Nonstop1h 11m
Deal found 9/14![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 9/14. 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 3/64:00 pm -
2 stops7h 18m
Fri 3/128:15 pm -
1 stop3h 31m
Deal found 9/14![Delta logo]()
$493
This Southwest deal was found by Cheapflights users on 9/15. 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 10/67:10 am -
2 stops7h 20m
Wed 10/712:40 pm -
1 stop6h 10m
Deal found 9/15![Southwest logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/12. 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 10/176:00 am -
Nonstop1h 14m
Fri 10/308:15 am -
Nonstop1h 23m
Deal found 9/12![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 9/13. 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 10/24:00 pm -
2 stops6h 47m
Mon 10/57:25 pm -
1 stop4h 29m
Deal found 9/13![Delta logo]()
$493
This Southwest deal was found by Cheapflights users on 9/16. 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 11/810:45 am -
Nonstop1h 20m
Mon 11/910:25 pm -
Nonstop1h 25m
Deal found 9/16![Southwest logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/12. 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 10/176:00 am -
Nonstop1h 14m
Sat 10/3110:35 pm -
Nonstop1h 24m
Deal found 9/12![United Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 9/15. 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 10/96:00 am -
Nonstop1h 20m
Mon 10/126:20 am -
1 stop7h 40m
Deal found 9/15![Southwest logo]()
$357
Last-minute flights from Cleveland to AnnapolisDiscover last-minute flight deals from Cleveland to Annapolis. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Annapolis. Data last updated September 17, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/37:00 am -
1 stop9h 46m
Mon 10/56:00 am -
1 stop6h 04m
Deal found 9/12![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/63:45 pm -
1 stop17h 40m
Tue 10/139:12 pm -
1 stop23h 40m
Deal found 9/13![Frontier logo]()
$141
This Expedia deal was found by Cheapflights users on 9/15. 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 10/66:00 am -
1 stop8h 11m
Wed 10/79:27 am -
1 stop15h 03m
Deal found 9/15![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/99:59 pm -
1 stop10h 21m
Mon 10/129:52 pm -
1 stop11h 05m
Deal found 9/16![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/129:59 pm -
1 stop10h 21m
Mon 10/199:52 pm -
1 stop11h 05m
Deal found 9/13![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/136:00 am -
1 stop8h 20m
Tue 10/207:05 pm -
1 stop13h 52m
Deal found 9/13![Frontier logo]()
$131
This Expedia deal was found by Cheapflights users on 9/12. 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.
Wed 10/149:59 pm -
1 stop10h 21m
Mon 10/199:52 pm -
1 stop11h 05m
Deal found 9/12![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/157:00 am -
1 stop9h 47m
Mon 10/196:24 am -
1 stop5h 45m
Deal found 9/13![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/169:59 pm -
1 stop10h 21m
Mon 10/199:52 pm -
1 stop11h 05m
Deal found 9/13![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/203:46 pm -
1 stop8h 48m
Thu 10/225:40 am -
1 stop6h 29m
Deal found 9/14![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/213:46 pm -
1 stop8h 48m
Sat 10/245:40 am -
1 stop15h 12m
Deal found 9/12![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/239:59 pm -
1 stop10h 21m
Mon 10/269:52 pm -
1 stop11h 14m
Deal found 9/14![Frontier logo]()
$146
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 September 17, 2026.
Search for one-way flight options from Cleveland to Annapolis. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/169:59 pm -
1 stop10h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$57
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/139:59 pm -
1 stop16h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$59
This Expedia deal was found by Cheapflights users on 9/16. 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.
Wed 10/149:59 pm -
1 stop12h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$77
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:59 pm -
1 stop10h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$77
This CheapOair deal was found by Cheapflights users on 9/16. 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.
Mon 10/269:59 pm -
1 stop12h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/149:59 pm -
1 stop10h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$78
This Orbitz deal was found by Cheapflights users on 9/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/129:59 pm -
1 stop16h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Frontier logo]()
$79
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:30 am -
1 stop7h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 11/103:46 pm -
1 stop18h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/117:00 am -
1 stop17h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/163:46 pm -
1 stop18h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$84
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:46 pm -
1 stop8h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$85
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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $128 (Kiwi.com) |
One-way from | $57 (Kiwi.com) |
Popular in | June |
Cheapest in | October |
Average price | $253 |
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 7,457,451 searches. Data last updated September 17, 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 Cleveland Hopkins Intl - BWI Baltimore/Washington
CLEBWI
Cleveland Hopkins Intl
Wed 10/14
7:10 am-1:10 pm
2 stops6h 00m
Baltimore/Washington
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$122
ClevelandBaltimore
CLE Cleveland Hopkins Intl - BWI Baltimore/Washington
CLEBWI
Cleveland Hopkins Intl
Sat 11/14
3:30 pm-4:50 pm
Nonstop1h 20m
Baltimore/Washington
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$124
ClevelandBaltimore
CLE Cleveland Hopkins Intl - BWI Baltimore/Washington
CLEBWI
Cleveland Hopkins Intl
Tue 10/13
4:20 pm-5:35 pm
Nonstop1h 15m
Baltimore/Washington
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$124
ClevelandWashington, D.C.
CLE Cleveland Hopkins Intl - IAD Washington, D.C. Dulles Intl
CLEIAD
Cleveland Hopkins Intl
Fri 10/9
9:59 pm-10:17 am
1 stop12h 18m
Washington, D.C. Dulles Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$134
ClevelandWashington, D.C.
CLE Cleveland Hopkins Intl - IAD Washington, D.C. Dulles Intl
CLEIAD
Cleveland Hopkins Intl
Sun 10/18
6:47 pm-12:50 pm
1 stop18h 03m
Washington, D.C. Dulles Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$137
ClevelandBaltimore
CLE Cleveland Hopkins Intl - BWI Baltimore/Washington
CLEBWI
Cleveland Hopkins Intl
Mon 11/9
5:55 am-7:25 am
Nonstop1h 30m
Baltimore/Washington
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$143
ClevelandBaltimore
CLE Cleveland Hopkins Intl - BWI Baltimore/Washington
CLEBWI
Cleveland Hopkins Intl
Mon 12/14
5:30 am-7:00 am
Nonstop1h 30m
Baltimore/Washington
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$143
ClevelandWashington, D.C.
CLE Cleveland Hopkins Intl - DCA Washington, D.C. Reagan-National
CLEDCA
Cleveland Hopkins Intl
Fri 10/16
7:59 pm-9:10 am
1 stop13h 11m
Washington, D.C. Reagan-National
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$158
ClevelandWashington, D.C.
CLE Cleveland Hopkins Intl - DCA Washington, D.C. Reagan-National
CLEDCA
Cleveland Hopkins Intl
Sat 11/7
1:25 pm-6:10 pm
1 stop4h 45m
Washington, D.C. Reagan-National
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$161
ClevelandBaltimore
CLE Cleveland Hopkins Intl - BWI Baltimore/Washington
CLEBWI
Cleveland Hopkins Intl
Fri 10/9
12:40 pm-1:55 pm
Nonstop1h 15m
Baltimore/Washington
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$161
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 September 17, 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 September 17, 2026.
The most flights from CLE to AP9 are scheduled on a Monday (17 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (4 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 $199 and $304 in October.The cheapest round-trip price found within the last 5 days was $128 on Frontier (Oct 16-Oct 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 September 12, 2026.
Travelers seeking maximum savings on their Cleveland to Annapolis flight should consider departing on Saturday at noon 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 September 17, 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.
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Related info for your journey
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Cleveland and Annapolis flights
Browse other Cleveland and Annapolis flight options. Last updated on September 17, 2026.
Other flights from Cleveland
Browse through other flights departing from Cleveland. Flights are based on user searches made on Cheapflights and were last updated on September 17, 2026.
Popular flight searches
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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 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$117 | Average$317 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$126 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$388 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$159 | Average$339 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$166 | Average$313 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$225 | Average$293 | FlexibilityNo cancel fee | On-time62% |