$55+ Cheap flights from Orlando (ORL) 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — IAD
Sep 28 — Oct 51
Round-trip
1 adult, Economy
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Find cheap flights from Orlando 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 Orlando to Annapolis are usually found in February or September, booked 45 days in advance, depart on a Friday or Thursday and return on a Monday
Cheap flight deals from Orlando to Annapolis
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Cheapest flights from Orlando to AnnapolisExplore the most affordable flight options available from Orlando to Annapolis. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 29, 2026.
Explore the most affordable flight options available from Orlando to Annapolis. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 29, 2026.
This Breeze Airways deal was found by Cheapflights users on 8/27. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/141:57 pm -
1 stop3h 59m
Mon 9/216:36 pm -
1 stop3h 58m
Deal found 8/27![Breeze Airways logo]()
$115
This Breeze Airways deal was found by Cheapflights users on 8/28. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:07 pm -
1 stop3h 59m
Mon 9/216:36 pm -
1 stop3h 58m
Deal found 8/28![Breeze Airways logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:06 am -
Nonstop2h 11m
Mon 9/286:36 pm -
1 stop3h 58m
Deal found 8/24![Multiple Airlines logo]()
$117
This Cheapflightsfares deal was found by Cheapflights users on 8/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:06 am -
Nonstop2h 11m
Wed 9/3011:12 am -
Nonstop2h 22m
Deal found 8/25![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:16 am -
Nonstop2h 11m
Mon 9/286:36 pm -
1 stop3h 58m
Deal found 8/25![Multiple Airlines logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1612:50 pm -
1 stop8h 40m
Tue 9/2210:22 am -
1 stop6h 47m
Deal found 8/24![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/226:12 am -
Nonstop2h 19m
Tue 9/299:25 pm -
1 stop10h 44m
Deal found 8/23![Frontier logo]()
$123
This Priceline deal was found by Cheapflights users on 8/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:06 am -
Nonstop2h 11m
Mon 9/216:36 pm -
1 stop3h 58m
Deal found 8/24![Multiple Airlines logo]()
$124
This Frontier deal was found by Cheapflights users on 8/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:21 pm -
Nonstop2h 23m
Sat 9/1910:22 am -
1 stop11h 37m
Deal found 8/24![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 10/312:50 pm -
1 stop11h 20m
Sat 10/1011:12 am -
Nonstop2h 26m
Deal found 8/23![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/1912:50 pm -
1 stop9h 05m
Tue 9/223:10 pm -
Nonstop2h 36m
Deal found 8/23![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Sat 9/51:50 pm -
Nonstop2h 26m
Mon 9/76:24 am -
Nonstop2h 27m
Deal found 8/26![Frontier logo]()
$128
Best flights from Orlando to AnnapolisDiscover carefully curated flight deals from Orlando to Annapolis that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 29, 2026.
Discover carefully curated flight deals from Orlando to Annapolis that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 29, 2026.
This Breeze Airways deal was found by Cheapflights users on 8/25. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:07 pm -
1 stop3h 59m
Mon 9/216:36 pm -
1 stop3h 58m
Deal found 8/25![Breeze Airways logo]()
$125
This Super.com deal was found by Cheapflights users on 8/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:00 am -
Nonstop2h 21m
Fri 11/277:41 pm -
Nonstop2h 30m
Deal found 8/23![Frontier logo]()
$215
This Delta deal was found by Cheapflights users on 8/23. 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 9/235:30 am -
1 stop6h 00m
Wed 9/306:10 am -
1 stop5h 08m
Deal found 8/23![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 8/23. 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 9/2311:10 am -
1 stop7h 25m
Wed 9/3012:00 pm -
1 stop6h 45m
Deal found 8/23![Southwest logo]()
$229
This United Airlines deal was found by Cheapflights users on 8/23. 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.
Tue 9/159:37 am -
Nonstop2h 13m
Wed 10/2110:33 pm -
Nonstop2h 26m
Deal found 8/23![United Airlines logo]()
$237
This JetBlue deal was found by Cheapflights users on 8/23. 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 11/196:35 pm -
1 stop4h 49m
Fri 11/273:10 pm -
Nonstop2h 34m
Deal found 8/23![JetBlue logo]()
$286
This Breeze Airways deal was found by Cheapflights users on 8/26. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/231:57 pm -
1 stop3h 59m
Mon 11/306:36 pm -
1 stop3h 58m
Deal found 8/26![Breeze Airways logo]()
$167
This Southwest deal was found by Cheapflights users on 8/27. 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 9/248:55 pm -
Nonstop2h 25m
Thu 10/16:10 pm -
Nonstop2h 25m
Deal found 8/27![Southwest logo]()
$237
This Breeze Airways deal was found by Cheapflights users on 8/28. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/281:57 pm -
1 stop3h 59m
Fri 10/26:36 pm -
1 stop3h 58m
Deal found 8/28![Breeze Airways logo]()
$219
This Delta deal was found by Cheapflights users on 8/26. 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 9/246:00 am -
1 stop5h 45m
Tue 9/296:10 am -
1 stop5h 08m
Deal found 8/26![Delta logo]()
$253
This Southwest deal was found by Cheapflights users on 8/25. 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 9/2410:15 am -
1 stop4h 30m
Mon 9/286:00 am -
Nonstop2h 25m
Deal found 8/25![Southwest logo]()
$243
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Mon 11/164:30 pm -
Nonstop2h 14m
Thu 11/199:52 am -
Nonstop2h 31m
Deal found 8/25![United Airlines logo]()
$271
This Cheapflightsfares deal was found by Cheapflights users on 8/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2012:50 pm -
1 stop11h 20m
Sun 9/2712:30 pm -
1 stop13h 15m
Deal found 8/23![Frontier logo]()
$277
This Southwest deal was found by Cheapflights users on 8/27. 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 9/221:50 pm -
Nonstop2h 15m
Thu 11/197:25 am -
1 stop6h 35m
Deal found 8/27![Southwest logo]()
$247
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Tue 11/1711:50 am -
Nonstop2h 13m
Thu 11/198:15 am -
1 stop6h 28m
Deal found 8/25![United Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 8/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/84:40 pm -
1 stop7h 04m
Tue 9/152:00 pm -
1 stop5h 32m
Deal found 8/24![Delta logo]()
$281
This Southwest deal was found by Cheapflights users on 8/24. 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 9/151:00 pm -
1 stop6h 10m
Wed 9/166:05 am -
2 stops8h 10m
Deal found 8/24![Southwest logo]()
$262
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Tue 9/229:37 am -
Nonstop2h 13m
Sat 9/2610:33 pm -
Nonstop2h 26m
Deal found 8/25![United Airlines logo]()
$298
This Southwest deal was found by Cheapflights users on 8/28. 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 10/31:45 pm -
Nonstop2h 10m
Mon 10/56:10 am -
Nonstop2h 20m
Deal found 8/28![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Sat 11/217:17 pm -
Nonstop2h 11m
Wed 11/2510:32 pm -
Nonstop2h 27m
Deal found 8/27![United Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 8/23. 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 9/2510:45 am -
1 stop5h 25m
Tue 9/292:40 pm -
1 stop7h 30m
Deal found 8/23![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 8/28. 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.
Sun 9/2710:20 am -
1 stop4h 30m
Tue 9/296:00 pm -
Nonstop2h 40m
Deal found 8/28![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 8/27. 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 11/216:35 pm -
Nonstop2h 15m
Wed 11/256:40 pm -
Nonstop2h 30m
Deal found 8/27![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 8/27. 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.
Fri 11/209:00 am -
Nonstop2h 20m
Mon 11/231:10 pm -
1 stop7h 10m
Deal found 8/27![Southwest logo]()
$281
This KAYAK deal was found by Cheapflights users on 8/25. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/19:55 am -
1 stop4h 58m
Wed 9/23:49 pm -
1 stop6h 27m
Deal found 8/25![JetBlue logo]()
$627
This Southwest deal was found by Cheapflights users on 8/23. 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 10/27:10 am -
1 stop5h 15m
Mon 10/511:40 am -
2 stops7h 30m
Deal found 8/23![Southwest logo]()
$286
This United Airlines deal was found by Cheapflights users on 8/25. 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 9/197:22 am -
2 stops14h 07m
Sun 9/206:05 am -
1 stop8h 53m
Deal found 8/25![United Airlines logo]()
$656
This Southwest deal was found by Cheapflights users on 8/26. 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.
Sat 9/198:15 am -
2 stops6h 35m
Sun 9/203:45 pm -
1 stop4h 15m
Deal found 8/26![Southwest logo]()
$401
This United Airlines deal was found by Cheapflights users on 8/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:20 pm -
1 stop7h 22m
Wed 12/26:15 am -
2 stops8h 57m
Deal found 8/26![United Airlines logo]()
$715
This Southwest deal was found by Cheapflights users on 8/24. 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.
Thu 11/267:30 am -
2 stops6h 50m
Mon 11/301:10 pm -
1 stop5h 45m
Deal found 8/24![Southwest logo]()
$432
Last-minute flights from Orlando to AnnapolisDiscover last-minute flight deals from Orlando to Annapolis. Data last updated August 29, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Annapolis. Data last updated August 29, 2026 and is based on user searches.
This deal was found by Cheapflights users on 8/25. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:50 am -
Nonstop2h 17m
Sun 9/64:52 pm -
Nonstop2h 29m
Deal found 8/25![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Sat 9/51:50 pm -
Nonstop2h 26m
Mon 9/76:24 am -
Nonstop2h 27m
Deal found 8/26![Frontier logo]()
$128
This CheapOair deal was found by Cheapflights users on 8/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/61:50 pm -
Nonstop2h 17m
Tue 9/2211:12 am -
Nonstop2h 22m
Deal found 8/25![Frontier logo]()
$152
This Expedia deal was found by Cheapflights users on 8/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/61:50 pm -
Nonstop2h 17m
Fri 9/186:46 pm -
1 stop3h 58m
Deal found 8/25![Multiple Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1612:50 pm -
1 stop8h 40m
Tue 9/2210:22 am -
1 stop6h 47m
Deal found 8/24![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 8/27. 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.
Thu 9/175:19 pm -
1 stop5h 24m
Mon 9/219:25 pm -
1 stop10h 44m
Deal found 8/27![Frontier logo]()
$131
This Frontier deal was found by Cheapflights users on 8/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:21 pm -
Nonstop2h 23m
Sat 9/1910:22 am -
1 stop11h 37m
Deal found 8/24![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/1912:50 pm -
1 stop9h 05m
Tue 9/223:10 pm -
Nonstop2h 36m
Deal found 8/23![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Sat 9/199:30 am -
1 stop7h 16m
Mon 9/289:25 pm -
1 stop10h 44m
Deal found 8/26![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/226:12 am -
Nonstop2h 19m
Tue 9/299:25 pm -
1 stop10h 44m
Deal found 8/23![Frontier logo]()
$123
This CheapOair deal was found by Cheapflights users on 8/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2211:49 am -
Nonstop2h 22m
Tue 10/69:27 am -
Nonstop2h 33m
Deal found 8/26![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:19 pm -
1 stop5h 24m
Sat 9/263:10 pm -
Nonstop2h 36m
Deal found 8/25![Frontier logo]()
$132
One-way flights from Orlando to AnnapolisSearch for one-way flight options from Orlando to Annapolis. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
Search for one-way flight options from Orlando to Annapolis. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
This Trip.com deal was found by Cheapflights users on 8/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:30 am -
1 stop12h 27m
Deal found 8/24![Frontier logo]()
$55
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:19 pm -
1 stop16h 06m
Deal found 8/24![Frontier logo]()
$56
This Super.com deal was found by Cheapflights users on 8/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:50 pm -
Nonstop2h 26m
Deal found 8/26![Frontier logo]()
$59
This CheapOair deal was found by Cheapflights users on 8/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:49 am -
Nonstop2h 22m
Deal found 8/25![Frontier logo]()
$60
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 10/194:53 pm -
1 stop23h 54m
Deal found 8/26![Frontier logo]()
$61
This Trip.com deal was found by Cheapflights users on 8/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:50 pm -
1 stop11h 20m
Deal found 8/28![Frontier logo]()
$62
This Jetabroad deal was found by Cheapflights users on 8/26. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/310:00 am -
1 stop8h 34m
Deal found 8/26![JetBlue logo]()
$62
This Trip.com deal was found by Cheapflights users on 8/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/712:50 pm -
1 stop11h 20m
Deal found 8/24![Frontier logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:19 pm -
1 stop23h 27m
Deal found 8/25![Frontier logo]()
$63
This Trip.com deal was found by Cheapflights users on 8/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:03 pm -
1 stop6h 40m
Deal found 8/28![Frontier logo]()
$64
This Trip.com deal was found by Cheapflights users on 8/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:50 pm -
1 stop20h 35m
Deal found 8/24![Frontier logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Sat 9/199:30 am -
1 stop7h 16m
Deal found 8/28![Frontier logo]()
$65
Find flight deals from Orlando to Annapolis
Keep the following information in mind while searching for Orlando to Annapolis flight deals. Data was last updated August 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $115 (Breeze Airways) |
One-way from | $55 (Trip.com) |
Popular in | June |
Cheapest in | February |
Average price | $175 |
Cheapflights Fare Finder
Customize your flight search to find flights from Orlando 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 August 29, 2026.
Use the filters below to find and compare flights from Orlando to Annapolis that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OrlandoWashington, D.C.
MCO Orlando - IAD Washington, D.C. Dulles Intl
MCOIAD
Orlando
Fri 9/18
2:07 pm-6:06 pm
1 stop3h 59m
Washington, D.C. Dulles Intl
Mon 9/21
6:36 pm-10:34 pm
1 stop3h 58m
$125
OrlandoWashington, D.C.
MCO Orlando - IAD Washington, D.C. Dulles Intl
MCOIAD
Orlando
Mon 11/23
1:57 pm-5:56 pm
1 stop3h 59m
Washington, D.C. Dulles Intl
Mon 11/30
6:36 pm-10:34 pm
1 stop3h 58m
$167
OrlandoWashington, D.C.
MCO Orlando - IAD Washington, D.C. Dulles Intl
MCOIAD
Orlando
Thu 11/19
8:00 am-10:21 am
Nonstop2h 21m
Washington, D.C. Dulles Intl
Fri 11/27
7:41 pm-10:11 pm
Nonstop2h 30m
$215
OrlandoWashington, D.C.
MCO Orlando - IAD Washington, D.C. Dulles Intl
MCOIAD
Orlando
Mon 9/28
1:57 pm-5:56 pm
1 stop3h 59m
Washington, D.C. Dulles Intl
Fri 10/2
6:36 pm-10:34 pm
1 stop3h 58m
$219
OrlandoWashington, D.C.
MCO Orlando - IAD Washington, D.C. Dulles Intl
MCOIAD
Orlando
Wed 9/23
5:30 am-11:30 am
1 stop6h 00m
Washington, D.C. Dulles Intl
Wed 9/30
6:10 am-11:18 am
1 stop5h 08m
$229
OrlandoWashington, D.C.
MCO Orlando - DCA Washington, D.C. Reagan-National
MCODCA
Orlando
Wed 9/23
11:10 am-6:35 pm
1 stop7h 25m
Washington, D.C. Reagan-National
Wed 9/30
12:00 pm-6:45 pm
1 stop6h 45m
$229
OrlandoWashington, D.C.
MCO Orlando - IAD Washington, D.C. Dulles Intl
MCOIAD
Orlando
Tue 9/15
9:37 am-11:50 am
Nonstop2h 13m
Washington, D.C. Dulles Intl
Wed 10/21
10:33 pm-12:59 am
Nonstop2h 26m
$237
OrlandoBaltimore
MCO Orlando - BWI Baltimore/Washington
MCOBWI
Orlando
Thu 9/24
8:55 pm-11:20 pm
Nonstop2h 25m
Baltimore/Washington
Thu 10/1
6:10 pm-8:35 pm
Nonstop2h 25m
$237
OrlandoWashington, D.C.
MCO Orlando - DCA Washington, D.C. Reagan-National
MCODCA
Orlando
Thu 9/24
10:15 am-2:45 pm
1 stop4h 30m
Washington, D.C. Reagan-National
Mon 9/28
6:00 am-8:25 am
Nonstop2h 25m
$243
OrlandoWashington, D.C.
MCO Orlando - DCA Washington, D.C. Reagan-National
MCODCA
Orlando
Tue 9/22
1:50 pm-4:05 pm
Nonstop2h 15m
Washington, D.C. Reagan-National
Thu 11/19
7:25 am-2:00 pm
1 stop6h 35m
$247
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Orlando to Annapolis
Have a flexible travel schedule? Discover the best time to fly to Annapolis from Orlando with our price prediction graph.
MCO-BWI
MCO-IAD
MCO-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 Orlando to Annapolis
ORL-AP9
MCO-BWI
MCO-IAD
MCO-DCA
What is the cheapest time of day to fly from ORL to AP9?
Find hourly flight availability from Orlando 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 29, 2026.
It’s optimal to fly from Orlando to Annapolis in the afternoon. By choosing this option you can save up to 54% on the cost of your flight, compared to a flight at noon.
Weekly flight availability from Orlando to Annapolis
Explore weekly flight availability from Orlando 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 29, 2026.
The most flights from ORL to AP9 are scheduled on a Thursday (21 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Orlando to Annapolis?
Airfare is typical for this route at the moment.
Orlando to Annapolis flights typically cost between $84 and $183 in September.The cheapest round-trip price found within the last 5 days was $115 on Breeze Airways (Sep 14-Sep 21).
What is the cheapest day to fly from Orlando to Annapolis?
Use this chart to determine the cheapest time to fly round-trip from Orlando to Annapolis. Price data was last updated on August 22, 2026.
Travelers seeking maximum savings on their Orlando to Annapolis flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday at noon 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 29, 2026.
Read through reviews of airlines operating flights from Orlando to Annapolis, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Orlando 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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Orlando and Annapolis flights
Browse other Orlando and Annapolis flight options. Last updated on August 29, 2026.
Other flights from Orlando
Browse through other flights departing from Orlando. Flights are based on user searches made on Cheapflights and were last updated on August 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from Orlando to Annapolis
Discover the top 7 airlines that operate flights from Orlando 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 August 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$47 | Average$167 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$76 | Average$153 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$79 | Average$301 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$98 | Average$220 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$369 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$257 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$137 | Average$287 | FlexibilityNo cancel fee | On-time69% |