$105+ Cheap flights from Boston (BOS) to Chesapeake, VA
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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
Sep 18 — Sep 251
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Chesapeake 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 Chesapeake are usually found in October or January, booked 46 days in advance, depart on a Wednesday or Thursday and return on a Friday
Cheap flight deals from Boston to Chesapeake
Cheapest
Best
Last-minute
One-way
Cheapest flights from Boston to ChesapeakeExplore the most affordable flight options available from Boston to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 19, 2026.
Explore the most affordable flight options available from Boston to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 19, 2026.
This Frontier deal was found by Cheapflights users on 8/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1711:17 am -
1 stop7h 31m
Wed 9/237:43 pm -
1 stop14h 39m
Deal found 8/17![Frontier logo]()
$215
This Faresmojo deal was found by Cheapflights users on 8/16. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:15 pm -
Nonstop1h 59m
Tue 9/228:00 am -
1 stop8h 29m
Deal found 8/16![JetBlue logo]()
$225
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:36 am -
1 stop7h 12m
Sat 9/197:43 pm -
1 stop15h 15m
Deal found 8/17![Frontier logo]()
$229
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:17 am -
1 stop7h 31m
Sun 10/47:43 pm -
1 stop15h 08m
Deal found 8/17![Frontier logo]()
$233
This Priceline deal was found by Cheapflights users on 8/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:36 am -
1 stop7h 12m
Sat 9/197:27 pm -
Nonstop2h 19m
Deal found 8/17![Multiple Airlines logo]()
$234
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:36 am -
1 stop7h 12m
Sat 9/197:43 pm -
1 stop15h 15m
Deal found 8/17![Frontier logo]()
$235
This Priceline deal was found by Cheapflights users on 8/16. 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.
Thu 9/1711:17 am -
1 stop7h 31m
Tue 9/227:27 pm -
Nonstop2h 19m
Deal found 8/16![Multiple Airlines logo]()
$238
This CheapOair deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/164:35 pm -
Nonstop1h 48m
Wed 9/237:43 pm -
1 stop14h 39m
Deal found 8/18![Multiple Airlines logo]()
$240
This Priceline deal was found by Cheapflights users on 8/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:36 am -
1 stop7h 12m
Sat 9/267:27 pm -
Nonstop2h 19m
Deal found 8/14![Multiple Airlines logo]()
$243
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:35 pm -
Nonstop1h 48m
Sat 9/127:43 pm -
1 stop15h 15m
Deal found 8/17![Multiple Airlines logo]()
$244
Best flights from Boston to ChesapeakeDiscover carefully curated flight deals from Boston to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 19, 2026.
Discover carefully curated flight deals from Boston to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 19, 2026.
This JetBlue deal was found by Cheapflights users on 8/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:59 pm -
Nonstop1h 51m
Wed 10/215:33 pm -
Nonstop2h 21m
Deal found 8/15![JetBlue logo]()
$257
This Delta deal was found by Cheapflights users on 8/14. 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 10/139:15 am -
Nonstop1h 58m
Tue 10/205:25 pm -
1 stop7h 55m
Deal found 8/14![Delta logo]()
$267
This United Airlines deal was found by Cheapflights users on 8/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:35 pm -
2 stops8h 08m
Sat 9/197:59 pm -
1 stop4h 00m
Deal found 8/17![United Airlines logo]()
$282
This Southwest deal was found by Cheapflights users on 8/14. 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.
Wed 9/165:25 am -
2 stops11h 55m
Tue 9/2212:15 pm -
1 stop3h 45m
Deal found 8/14![Southwest logo]()
$308
This JetBlue deal was found by Cheapflights users on 8/14. 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.
Sat 10/173:59 pm -
Nonstop1h 51m
Tue 10/205:33 pm -
Nonstop2h 21m
Deal found 8/14![JetBlue logo]()
$257
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:55 am -
1 stop5h 16m
Sat 9/195:55 pm -
Nonstop2h 05m
Deal found 8/18![Delta logo]()
$267
This United Airlines deal was found by Cheapflights users on 8/15. 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.
Mon 9/213:35 pm -
2 stops8h 08m
Wed 9/2310:49 am -
1 stop3h 33m
Deal found 8/15![United Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 8/15. 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 10/19:05 am -
Nonstop1h 53m
Sun 10/47:19 pm -
1 stop5h 58m
Deal found 8/15![Delta logo]()
$287
This JetBlue deal was found by Cheapflights users on 8/16. 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 9/94:35 pm -
Nonstop1h 48m
Mon 9/147:27 pm -
Nonstop2h 19m
Deal found 8/16![JetBlue logo]()
$292
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:05 am -
1 stop5h 21m
Mon 9/286:20 pm -
1 stop4h 06m
Deal found 8/18![Delta logo]()
$287
This JetBlue deal was found by Cheapflights users on 8/16. 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 10/283:59 pm -
Nonstop1h 55m
Sun 11/16:50 pm -
Nonstop1h 40m
Deal found 8/16![JetBlue logo]()
$292
This JetBlue deal was found by Cheapflights users on 8/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/14:45 pm -
Nonstop1h 48m
Sun 10/47:37 pm -
Nonstop1h 55m
Deal found 8/17![JetBlue logo]()
$327
Last-minute flights from Boston to ChesapeakeDiscover last-minute flight deals from Boston to Chesapeake. Data last updated August 19, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Chesapeake. Data last updated August 19, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:35 pm -
Nonstop1h 48m
Sat 9/127:43 pm -
1 stop15h 15m
Deal found 8/17![Multiple Airlines logo]()
$244
This Priceline deal was found by Cheapflights users on 8/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:36 am -
1 stop7h 12m
Sat 9/197:27 pm -
Nonstop2h 19m
Deal found 8/17![Multiple Airlines logo]()
$234
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:36 am -
1 stop7h 12m
Sat 9/197:43 pm -
1 stop15h 15m
Deal found 8/17![Frontier logo]()
$235
This Frontier deal was found by Cheapflights users on 8/16. 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 9/1211:36 am -
1 stop7h 12m
Sun 9/137:43 pm -
1 stop15h 08m
Deal found 8/16![Frontier logo]()
$246
This CheapOair deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/164:35 pm -
Nonstop1h 48m
Wed 9/237:43 pm -
1 stop14h 39m
Deal found 8/18![Multiple Airlines logo]()
$240
This Frontier deal was found by Cheapflights users on 8/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1711:17 am -
1 stop7h 31m
Wed 9/237:43 pm -
1 stop14h 39m
Deal found 8/17![Frontier logo]()
$215
This Priceline deal was found by Cheapflights users on 8/16. 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.
Thu 9/1711:17 am -
1 stop7h 31m
Tue 9/227:27 pm -
Nonstop2h 19m
Deal found 8/16![Multiple Airlines logo]()
$238
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:36 am -
1 stop7h 12m
Sat 9/197:43 pm -
1 stop15h 15m
Deal found 8/17![Frontier logo]()
$229
This Priceline deal was found by Cheapflights users on 8/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:36 am -
1 stop7h 12m
Sat 9/267:27 pm -
Nonstop2h 19m
Deal found 8/14![Multiple Airlines logo]()
$243
This Faresmojo deal was found by Cheapflights users on 8/16. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:15 pm -
Nonstop1h 59m
Tue 9/228:00 am -
1 stop8h 29m
Deal found 8/16![JetBlue logo]()
$225
One-way flights from Boston to ChesapeakeSearch for one-way flight options from Boston to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
Search for one-way flight options from Boston to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
This Priceline deal was found by Cheapflights users on 8/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:47 am -
1 stop6h 59m
Deal found 8/14![Frontier logo]()
$105
This Faresmojo deal was found by Cheapflights users on 8/16. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:05 am -
Nonstop1h 53m
Deal found 8/16![JetBlue logo]()
$108
This Priceline deal was found by Cheapflights users on 8/15. 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.
Thu 10/2910:11 am -
1 stop7h 04m
Deal found 8/15![Frontier logo]()
$109
This Priceline deal was found by Cheapflights users on 8/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:36 am -
1 stop7h 12m
Deal found 8/14![Frontier logo]()
$114
This Frontier deal was found by Cheapflights users on 8/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:36 am -
1 stop7h 12m
Deal found 8/14![Frontier logo]()
$120
This Priceline deal was found by Cheapflights users on 8/15. 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 10/3010:11 am -
1 stop7h 04m
Deal found 8/15![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/194:35 pm -
Nonstop1h 48m
Deal found 8/18![JetBlue logo]()
$126
This JetBlue deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/154:35 pm -
Nonstop1h 48m
Deal found 8/19![JetBlue logo]()
$129
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:57 am -
1 stop26h 20m
Deal found 8/17![Frontier logo]()
$132
This Delta deal was found by Cheapflights users on 8/14. 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 8/293:05 pm -
Nonstop1h 59m
Deal found 8/14![Delta logo]()
$134
Find flight deals from Boston to Chesapeake
Keep the following information in mind while searching for Boston to Chesapeake flight deals. Data was last updated August 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $215 (Frontier) |
One-way from | $105 (Priceline) |
Popular in | November |
Cheapest in | October |
Average price | $303 |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Chesapeake that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 19, 2026.
Use the filters below to find and compare flights from Boston to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonNorfolk
BOS Boston Logan Intl - ORF Norfolk
BOSORF
Boston Logan Intl
Tue 10/20
3:59 pm-5:50 pm
Nonstop1h 51m
Norfolk
Wed 10/21
5:33 pm-7:54 pm
Nonstop2h 21m
$257
BostonNorfolk
BOS Boston Logan Intl - ORF Norfolk
BOSORF
Boston Logan Intl
Sat 10/17
3:59 pm-5:50 pm
Nonstop1h 51m
Norfolk
Tue 10/20
5:33 pm-7:54 pm
Nonstop2h 21m
$257
BostonNorfolk
BOS Boston Logan Intl - ORF Norfolk
BOSORF
Boston Logan Intl
Tue 10/13
9:15 am-11:13 am
Nonstop1h 58m
Norfolk
Tue 10/20
5:25 pm-1:20 am
1 stop7h 55m
$267
BostonNorfolk
BOS Boston Logan Intl - ORF Norfolk
BOSORF
Boston Logan Intl
Sat 9/12
8:55 am-2:11 pm
1 stop5h 16m
Norfolk
Sat 9/19
5:55 pm-8:00 pm
Nonstop2h 05m
$267
BostonNorfolk
BOS Boston Logan Intl - ORF Norfolk
BOSORF
Boston Logan Intl
Sat 9/12
3:35 pm-11:43 pm
2 stops8h 08m
Norfolk
Sat 9/19
7:59 pm-11:59 pm
1 stop4h 00m
$282
BostonNorfolk
BOS Boston Logan Intl - ORF Norfolk
BOSORF
Boston Logan Intl
Thu 10/1
9:05 am-10:58 am
Nonstop1h 53m
Norfolk
Sun 10/4
7:19 pm-1:17 am
1 stop5h 58m
$287
BostonNorfolk
BOS Boston Logan Intl - ORF Norfolk
BOSORF
Boston Logan Intl
Sat 9/26
6:05 am-11:26 am
1 stop5h 21m
Norfolk
Mon 9/28
6:20 pm-10:26 pm
1 stop4h 06m
$287
BostonNorfolk
BOS Boston Logan Intl - ORF Norfolk
BOSORF
Boston Logan Intl
Wed 9/9
4:35 pm-6:23 pm
Nonstop1h 48m
Norfolk
Mon 9/14
7:27 pm-9:46 pm
Nonstop2h 19m
$292
Quickest round-trip
BostonNorfolk
BOS Boston Logan Intl - ORF Norfolk
BOSORF
Boston Logan Intl
Wed 10/28
3:59 pm-5:54 pm
Nonstop1h 55m
Norfolk
Sun 11/1
6:50 pm-8:30 pm
Nonstop1h 40m
$292
BostonNorfolk
BOS Boston Logan Intl - ORF Norfolk
BOSORF
Boston Logan Intl
Wed 9/16
5:25 am-5:20 pm
2 stops11h 55m
Norfolk
Tue 9/22
12:15 pm-4:00 pm
1 stop3h 45m
$308
Showing 1-10 of 24 resultsSorted by cheapest first
Best time to book a flight from Boston to Chesapeake
Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Boston with our price prediction graph.
BOS-ORF
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 Chesapeake
BOS-C6E
BOS-ORF
What is the cheapest time of day to fly from BOS to C6E?
Find hourly flight availability from Boston to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 19, 2026.
It’s typically best to fly out from Boston to Chesapeake in the afternoon. Doing so could potentially save you 7% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Boston to Chesapeake
Explore weekly flight availability from Boston to Chesapeake. 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 19, 2026.
The most flights from BOS to C6E are scheduled on a Monday (18 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from Boston to Chesapeake?
Airfare is below average for this route at the moment.
Boston to Chesapeake flights typically cost between $243 and $387 in September.The cheapest round-trip price found within the last 5 days was $215 on Frontier (Sep 17-Sep 23).
What is the cheapest day to fly from Boston to Chesapeake?
Use this chart to determine the cheapest time to fly round-trip from Boston to Chesapeake. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their Boston to Chesapeake flight should consider departing on Thursday at noon when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chesapeake
Get insights into the airlines that provide service to Chesapeake. 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 Chesapeake. Reviews last updated August 19, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Boston to Chesapeake have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
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Boston and Chesapeake flights
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Top 6 airlines flying from Boston to Chesapeake
Discover the top 6 airlines that operate flights from Boston to Chesapeake. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$103 | Average$312 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$106 | Average$191 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$120 | Average$276 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$324 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$166 | Average$311 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$166 | Average$414 | FlexibilityNo cancel fee | On-time71% |