$68+ Cheap flights from Boston (BOS) 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — IAD
Oct 17 — Oct 241
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Boston 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 Boston Logan Intl to Annapolis are usually found in December or January, booked 79 days in advance, depart on a Friday or Thursday and return on a Friday
Cheap flight deals from Boston to Annapolis
Cheapest
Best
Last-minute
One-way
Cheapest flights from Boston to AnnapolisExplore the most affordable flight options available from Boston 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 Boston to Annapolis. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
This Jetabroad 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:39 pm -
1 stop3h 36m
Tue 11/36:15 am -
1 stop4h 26m
Deal found 9/12![JetBlue logo]()
$119
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:10 pm -
1 stop4h 49m
Thu 10/156:20 am -
1 stop4h 41m
Deal found 9/12![JetBlue logo]()
$124
This JetBlue deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/236:40 pm -
1 stop4h 19m
Mon 10/266:15 am -
1 stop4h 26m
Deal found 9/11![JetBlue logo]()
$140
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:39 pm -
1 stop11h 54m
Wed 11/45:40 am -
1 stop6h 04m
Deal found 9/15![Frontier logo]()
$152
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:40 pm -
1 stop4h 19m
Sun 10/256:15 am -
1 stop4h 26m
Deal found 9/12![JetBlue logo]()
$154
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:20 pm -
Nonstop1h 47m
Tue 10/208:55 pm -
Nonstop1h 59m
Deal found 9/15![JetBlue logo]()
$162
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:26 pm -
1 stop4h 26m
Thu 11/266:00 am -
1 stop4h 35m
Deal found 9/12![JetBlue logo]()
$163
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:30 am -
Nonstop1h 42m
Wed 10/145:00 pm -
Nonstop2h 16m
Deal found 9/15![JetBlue logo]()
$165
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:59 pm -
Nonstop1h 48m
Tue 10/278:59 pm -
Nonstop1h 37m
Deal found 9/15![JetBlue logo]()
$167
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 10/206:05 am -
Nonstop1h 42m
Tue 10/276:15 am -
1 stop4h 26m
Deal found 9/16![JetBlue logo]()
$168
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.
Wed 10/146:40 pm -
1 stop4h 19m
Sat 10/179:00 pm -
Nonstop1h 59m
Deal found 9/16![JetBlue logo]()
$169
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:57 pm -
1 stop11h 37m
Sat 10/249:52 pm -
1 stop13h 10m
Deal found 9/15![Frontier logo]()
$169
Best flights from Boston to AnnapolisDiscover carefully curated flight deals from Boston 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 Boston 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 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.
Sat 10/318:00 am -
Nonstop1h 48m
Mon 11/26:15 am -
1 stop4h 26m
Deal found 9/16![JetBlue logo]()
$180
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.
Tue 10/277:41 pm -
Nonstop1h 47m
Fri 10/3010:19 pm -
Nonstop1h 40m
Deal found 9/15![United Airlines logo]()
$184
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.
Tue 11/109:15 pm -
Nonstop1h 47m
Sat 11/147:00 am -
Nonstop1h 37m
Deal found 9/16![Delta logo]()
$189
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 10/169:45 pm -
Nonstop1h 35m
Mon 10/1910:30 pm -
Nonstop1h 40m
Deal found 9/14![Southwest logo]()
$222
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.
Wed 12/1611:20 am -
Nonstop1h 52m
Mon 1/117:45 pm -
Nonstop1h 36m
Deal found 9/16![Delta logo]()
$189
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 10/1510:51 am -
1 stop5h 32m
Mon 10/1910:25 pm -
Nonstop1h 44m
Deal found 9/15![United Airlines logo]()
$217
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:00 pm -
1 stop3h 59m
Tue 10/66:30 am -
1 stop4h 46m
Deal found 9/14![JetBlue logo]()
$221
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 12/165:30 am -
Nonstop1h 40m
Sun 1/108:25 pm -
Nonstop1h 30m
Deal found 9/16![Southwest logo]()
$228
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:35 am -
Nonstop1h 49m
Tue 10/135:36 pm -
1 stop6h 23m
Deal found 9/15![Delta logo]()
$215
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:40 pm -
1 stop4h 19m
Sun 10/256:15 am -
1 stop4h 26m
Deal found 9/12![JetBlue logo]()
$235
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 11/215:57 pm -
1 stop4h 28m
Sun 11/228:37 am -
1 stop3h 49m
Deal found 9/16![United Airlines logo]()
$242
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
1 stop4h 09m
Sun 10/256:00 am -
Nonstop1h 40m
Deal found 9/15![Delta logo]()
$226
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.
Fri 10/2310:10 pm -
Nonstop1h 35m
Sun 10/256:30 am -
Nonstop1h 35m
Deal found 9/16![Southwest logo]()
$260
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:10 am -
Nonstop1h 49m
Wed 10/286:15 am -
1 stop4h 26m
Deal found 9/14![JetBlue logo]()
$247
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.
Fri 11/69:00 pm -
Nonstop1h 45m
Sun 11/88:05 am -
Nonstop1h 35m
Deal found 9/13![Southwest logo]()
$260
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:20 pm -
Nonstop1h 47m
Sun 10/256:15 am -
1 stop4h 26m
Deal found 9/13![JetBlue logo]()
$247
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.
Tue 11/1010:30 am -
1 stop3h 57m
Mon 11/1610:59 am -
1 stop6h 45m
Deal found 9/15![United Airlines logo]()
$273
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:00 am -
1 stop5h 50m
Tue 10/206:32 pm -
1 stop4h 36m
Deal found 9/15![Delta logo]()
$253
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 11/171:20 pm -
Nonstop1h 35m
Sun 11/228:05 am -
Nonstop1h 35m
Deal found 9/13![Southwest logo]()
$276
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 11/179:37 am -
Nonstop1h 54m
Sun 11/225:20 pm -
1 stop4h 08m
Deal found 9/13![Delta logo]()
$257
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 10/2912:00 pm -
1 stop4h 35m
Mon 11/212:37 pm -
1 stop5h 57m
Deal found 9/15![United Airlines logo]()
$297
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:40 pm -
1 stop4h 19m
Thu 10/152:08 pm -
Nonstop2h 04m
Deal found 9/12![JetBlue logo]()
$272
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.
Tue 11/246:00 am -
1 stop4h 17m
Fri 11/277:00 am -
Nonstop1h 40m
Deal found 9/14![Delta logo]()
$257
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.
Fri 11/135:35 am -
Nonstop1h 35m
Sun 11/156:30 am -
Nonstop1h 35m
Deal found 9/13![Southwest logo]()
$285
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 9/307:13 pm -
Nonstop1h 45m
Wed 10/71:10 pm -
Nonstop1h 45m
Deal found 9/15![United Airlines logo]()
$298
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:00 am -
1 stop4h 09m
Tue 10/135:05 pm -
1 stop6h 03m
Deal found 9/15![Delta logo]()
$264
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.
Sat 10/246:00 am -
1 stop5h 50m
Sat 10/3112:30 pm -
1 stop6h 36m
Deal found 9/13![Delta logo]()
$267
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.
Fri 10/95:45 am -
Nonstop1h 35m
Tue 10/1310:15 pm -
Nonstop1h 44m
Deal found 9/12![United Airlines logo]()
$352
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 10/276:00 am -
1 stop4h 09m
Tue 10/275:18 pm -
1 stop5h 06m
Deal found 9/13![Delta logo]()
$267
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/411:20 am -
Nonstop1h 52m
Sun 12/66:46 pm -
Nonstop1h 39m
Deal found 9/12![Delta logo]()
$285
Last-minute flights from Boston to AnnapolisDiscover last-minute flight deals from Boston to Annapolis. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Annapolis. Data last updated September 17, 2026 and is based on user searches.
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:10 pm -
1 stop4h 49m
Thu 10/156:20 am -
1 stop4h 41m
Deal found 9/12![JetBlue logo]()
$124
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:30 am -
Nonstop1h 42m
Wed 10/145:00 pm -
Nonstop2h 16m
Deal found 9/15![JetBlue logo]()
$165
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.
Wed 10/146:40 pm -
1 stop4h 19m
Sat 10/179:00 pm -
Nonstop1h 59m
Deal found 9/16![JetBlue logo]()
$169
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 10/149:30 am -
Nonstop1h 41m
Sat 10/1710:15 pm -
Nonstop1h 44m
Deal found 9/16![United Airlines logo]()
$171
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:20 pm -
Nonstop1h 47m
Tue 10/208:55 pm -
Nonstop1h 59m
Deal found 9/15![JetBlue logo]()
$162
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 10/206:05 am -
Nonstop1h 42m
Tue 10/276:15 am -
1 stop4h 26m
Deal found 9/16![JetBlue logo]()
$168
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:57 pm -
1 stop11h 37m
Sat 10/249:52 pm -
1 stop13h 10m
Deal found 9/15![Frontier logo]()
$169
This JetBlue deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/236:40 pm -
1 stop4h 19m
Mon 10/266:15 am -
1 stop4h 26m
Deal found 9/11![JetBlue logo]()
$140
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:40 pm -
1 stop4h 19m
Sun 10/256:15 am -
1 stop4h 26m
Deal found 9/12![JetBlue logo]()
$154
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:59 pm -
Nonstop1h 48m
Tue 10/278:59 pm -
Nonstop1h 37m
Deal found 9/15![JetBlue logo]()
$167
This Jetabroad 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:39 pm -
1 stop3h 36m
Tue 11/36:15 am -
1 stop4h 26m
Deal found 9/12![JetBlue logo]()
$119
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:39 pm -
1 stop11h 54m
Wed 11/45:40 am -
1 stop6h 04m
Deal found 9/15![Frontier logo]()
$152
One-way flights from Boston to AnnapolisSearch for one-way flight options from Boston to Annapolis. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
Search for one-way flight options from Boston to Annapolis. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/114:10 pm -
1 stop6h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![JetBlue logo]()
$68
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.
Tue 10/2711:12 am -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$76
This Jetabroad 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/64:47 pm -
Nonstop1h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![JetBlue logo]()
$76
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1211:34 am -
1 stop6h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$76
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:00 pm -
1 stop3h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![JetBlue logo]()
$79
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/72:19 pm -
Nonstop1h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![JetBlue logo]()
$80
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:42 am -
1 stop12h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$81
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1012:15 pm -
1 stop12h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$81
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3111:27 am -
1 stop12h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$82
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3111:27 am -
1 stop12h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$82
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:35 pm -
1 stop4h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![JetBlue logo]()
$83
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1012:15 pm -
1 stop11h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$84
Find flight deals from Boston to Annapolis
Keep the following information in mind while searching for Boston 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 | $119 (Jetabroad) |
One-way from | $68 (Super.com) |
Popular in | June |
Cheapest in | December |
Average price | $229 |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston 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 Boston to Annapolis that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonWashington, D.C.
BOS Boston Logan Intl - IAD Washington, D.C. Dulles Intl
BOSIAD
Boston Logan Intl
Tue 10/20
9:30 am-11:11 am
Nonstop1h 41m
Washington, D.C. Dulles Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$86
BostonBaltimore
BOS Boston Logan Intl - BWI Baltimore/Washington
BOSBWI
Boston Logan Intl
Tue 12/15
6:30 am-8:19 am
Nonstop1h 49m
Baltimore/Washington
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$86
Quickest round-trip
BostonWashington, D.C.
BOS Boston Logan Intl - IAD Washington, D.C. Dulles Intl
BOSIAD
Boston Logan Intl
Sat 10/17
5:45 am-7:20 am
Nonstop1h 35m
Washington, D.C. Dulles Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$86
BostonBaltimore
BOS Boston Logan Intl - BWI Baltimore/Washington
BOSBWI
Boston Logan Intl
Tue 12/15
7:55 am-9:40 am
Nonstop1h 45m
Baltimore/Washington
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$87
BostonWashington, D.C.
BOS Boston Logan Intl - IAD Washington, D.C. Dulles Intl
BOSIAD
Boston Logan Intl
Sat 10/31
5:57 pm-10:25 pm
1 stop4h 28m
Washington, D.C. Dulles Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$96
BostonWashington, D.C.
BOS Boston Logan Intl - DCA Washington, D.C. Reagan-National
BOSDCA
Boston Logan Intl
Sat 10/17
6:00 am-9:59 am
1 stop3h 59m
Washington, D.C. Reagan-National
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$96
BostonWashington, D.C.
BOS Boston Logan Intl - DCA Washington, D.C. Reagan-National
BOSDCA
Boston Logan Intl
Mon 10/19
9:45 pm-11:37 pm
Nonstop1h 52m
Washington, D.C. Reagan-National
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$99
BostonBaltimore
BOS Boston Logan Intl - BWI Baltimore/Washington
BOSBWI
Boston Logan Intl
Thu 11/5
3:45 pm-5:31 pm
Nonstop1h 46m
Baltimore/Washington
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$104
BostonWashington, D.C.
BOS Boston Logan Intl - IAD Washington, D.C. Dulles Intl
BOSIAD
Boston Logan Intl
Thu 11/12
9:30 am-11:15 am
Nonstop1h 45m
Washington, D.C. Dulles Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$106
BostonWashington, D.C.
BOS Boston Logan Intl - IAD Washington, D.C. Dulles Intl
BOSIAD
Boston Logan Intl
Fri 10/23
5:45 am-7:20 am
Nonstop1h 35m
Washington, D.C. Dulles Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$109
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Boston to Annapolis
Have a flexible travel schedule? Discover the best time to fly to Annapolis from Boston with our price prediction graph.
BOS-DCA
BOS-IAD
BOS-BWI
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 Boston to Annapolis
BOS-AP9
BOS-DCA
BOS-IAD
BOS-BWI
What is the cheapest time of day to fly from BOS to AP9?
Find hourly flight availability from Boston 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.
When flying from Boston to Annapolis, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 12% versus a flight at noon.
Weekly flight availability from Boston to Annapolis
Explore weekly flight availability from Boston 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 BOS to AP9 are scheduled on a Tuesday (20 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (16 on average).
How much does it cost to fly round-trip from Boston to Annapolis?
Airfare is below average for this route at the moment.
Boston to Annapolis flights typically cost between $171 and $368 in October.The cheapest round-trip price found within the last 5 days was $119 on JetBlue (Oct 27-Nov 3).
What is the cheapest day to fly from Boston to Annapolis?
Use this chart to determine the cheapest time to fly round-trip from Boston to Annapolis. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Boston to Annapolis flight should consider departing on Wednesday evenings when fares are most often at their lowest. Monday afternoons 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.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Boston to Annapolis to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentJoseph,Sep 2023
LAX - BWI
Related info for your journey
Find useful and relevant information for your journey from Boston to Annapolis. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Boston
Popular flights
Top destinations
Alternative routes for Boston to Annapolis
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Annapolis by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Boston to Annapolis by cabin class
Find flights from Boston to Annapolis, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Boston and Annapolis flights
Browse other Boston and Annapolis flight options. Last updated on September 17, 2026.
Other flights from Boston
Browse through other flights departing from Boston. Flights are based on user searches made on Cheapflights and were last updated on September 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Boston to Annapolis flights
Consider these flights traveling from Boston to Annapolis.
Top 6 airlines flying from Boston to Annapolis
Discover the top 6 airlines that operate flights from Boston 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$116 | Average$271 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$249 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$125 | Average$261 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$281 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$174 | Average$321 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$180 | Average$301 | FlexibilityNo cancel fee | On-time62% |