$84+ 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 3/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
Apr 16 — Apr 231
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 June or May, booked 73 days in advance, depart on a Monday or Friday 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 March 17, 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 March 17, 2026.
This KAYAK deal was found by Cheapflights users on 3/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:50 am
BOS
- ORF
Nonstop1h 42m
JetBlue
Wed 5/1311:24 am
ORF
- BOS
Nonstop1h 38m
JetBlue
Deal found 3/13![JetBlue logo]()
$197
This CheapOair deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/133:25 pm
BOS
- ORF
Nonstop1h 40m
Multiple Airlines
Mon 4/206:02 pm
ORF
- BOS
1 stop16h 19m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$199
This Cheapflightsfares deal was found by Cheapflights users on 3/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/303:25 pm
BOS
- ORF
Nonstop1h 48m
JetBlue
Wed 4/16:00 pm
ORF
- BOS
Nonstop1h 45m
JetBlue
Deal found 3/15![JetBlue logo]()
$202
This JetBlue deal was found by Cheapflights users on 3/12. 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 3/274:10 pm
BOS
- ORF
Nonstop1h 50m
JetBlue
Tue 3/316:00 pm
ORF
- BOS
Nonstop1h 45m
JetBlue
Deal found 3/12![JetBlue logo]()
$207
This Priceline deal was found by Cheapflights users on 3/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:07 am
BOS
- ORF
1 stop8h 22m
Multiple Airlines
Wed 5/2011:24 am
ORF
- BOS
Nonstop1h 38m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$210
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/289:50 am
BOS
- ORF
1 stop11h 57m
Spirit Airlines
Wed 4/16:45 am
ORF
- BOS
1 stop10h 09m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 3/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/23:25 pm
BOS
- ORF
Nonstop1h 40m
JetBlue
Thu 4/96:00 pm
ORF
- BOS
Nonstop1h 45m
JetBlue
Deal found 3/16![JetBlue logo]()
$212
This CheapOair deal was found by Cheapflights users on 3/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:07 am
BOS
- ORF
1 stop8h 22m
Multiple Airlines
Tue 5/1211:24 am
ORF
- BOS
Nonstop1h 38m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$215
This JetBlue deal was found by Cheapflights users on 3/14. 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.
Thu 4/23:25 pm
BOS
- ORF
Nonstop1h 40m
JetBlue
Mon 4/66:00 pm
ORF
- BOS
Nonstop1h 45m
JetBlue
Deal found 3/14![JetBlue logo]()
$216
This KAYAK deal was found by Cheapflights users on 3/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/73:25 pm
BOS
- ORF
Nonstop1h 40m
JetBlue
Tue 4/1411:24 am
ORF
- BOS
Nonstop1h 38m
JetBlue
Deal found 3/17![JetBlue logo]()
$217
This Southwest deal was found by Cheapflights users on 3/16. 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.
Tue 4/146:20 am
BOS
- ORF
1 stop5h 35m
Southwest
Wed 4/1512:45 pm
ORF
- BOS
2 stops9h 55m
Southwest
Deal found 3/16![Southwest logo]()
$222
This Expedia deal was found by Cheapflights users on 3/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:50 am
BOS
- ORF
Nonstop1h 42m
Multiple Airlines
Mon 5/412:31 pm
ORF
- BOS
1 stop13h 00m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$224
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 March 17, 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 March 17, 2026.
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:50 pm
BOS
- ORF
1 stop3h 45m
Southwest
Sat 6/65:40 pm
ORF
- BOS
1 stop5h 55m
Southwest
Deal found 3/15![Southwest logo]()
$217
This JetBlue deal was found by Cheapflights users on 3/12. 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.
Wed 7/223:15 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Sat 7/255:53 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 3/12![JetBlue logo]()
$222
This Delta deal was found by Cheapflights users on 3/15. 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.
Wed 8/129:00 am
BOS
- ORF
Nonstop1h 55m
Delta
Mon 8/176:00 am
ORF
- BOS
1 stop4h 25m
Delta
Deal found 3/15![Delta logo]()
$272
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/132:40 pm
BOS
- ORF
1 stop4h 42m
United Airlines
Tue 6/166:05 am
ORF
- BOS
1 stop4h 15m
United Airlines
Deal found 3/12![United Airlines logo]()
$277
This JetBlue deal was found by Cheapflights users on 3/12. 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 6/223:15 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Tue 6/305:53 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 3/12![JetBlue logo]()
$242
This JetBlue deal was found by Cheapflights users on 3/12. 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 7/33:15 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Fri 7/105:53 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 3/12![JetBlue logo]()
$257
This Delta deal was found by Cheapflights users on 3/16. 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.
Sun 9/132:25 pm
BOS
- ORF
Nonstop1h 52m
Delta
Sun 9/206:00 am
ORF
- BOS
1 stop3h 54m
Delta
Deal found 3/16![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 3/12. 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 5/13:32 pm
BOS
- ORF
2 stops8h 18m
United Airlines
Mon 5/46:15 am
ORF
- BOS
1 stop4h 03m
United Airlines
Deal found 3/12![United Airlines logo]()
$302
This JetBlue deal was found by Cheapflights users on 3/12. 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 7/183:15 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Fri 7/245:53 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 3/12![JetBlue logo]()
$272
This United Airlines deal was found by Cheapflights users on 3/16. 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 5/232:40 pm
BOS
- ORF
1 stop4h 42m
United Airlines
Sun 5/246:05 am
ORF
- BOS
1 stop4h 15m
United Airlines
Deal found 3/16![United Airlines logo]()
$342
This JetBlue deal was found by Cheapflights users on 3/14. 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.
Tue 4/73:25 pm
BOS
- ORF
Nonstop1h 40m
JetBlue
Thu 4/93:32 pm
ORF
- BOS
1 stop8h 45m
JetBlue
Deal found 3/14![JetBlue logo]()
$340
This JetBlue deal was found by Cheapflights users on 3/14. 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 7/53:15 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Sun 7/125:53 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 3/14![JetBlue logo]()
$352
Last-minute flights from Boston to ChesapeakeDiscover last-minute flight deals from Boston to Chesapeake. Data last updated March 17, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Chesapeake. Data last updated March 17, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 3/12. 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 3/274:10 pm
BOS
- ORF
Nonstop1h 50m
JetBlue
Wed 4/16:00 pm
ORF
- BOS
Nonstop1h 45m
JetBlue
Deal found 3/12![JetBlue logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/289:50 am
BOS
- ORF
1 stop11h 57m
Spirit Airlines
Wed 4/16:45 am
ORF
- BOS
1 stop10h 09m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 3/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/303:25 pm
BOS
- ORF
Nonstop1h 48m
JetBlue
Tue 3/316:00 pm
ORF
- BOS
Nonstop1h 45m
JetBlue
Deal found 3/16![JetBlue logo]()
$202
This Cheapflightsfares deal was found by Cheapflights users on 3/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/23:25 pm
BOS
- ORF
Nonstop1h 40m
JetBlue
Thu 4/96:00 pm
ORF
- BOS
Nonstop1h 45m
JetBlue
Deal found 3/16![JetBlue logo]()
$212
This JetBlue deal was found by Cheapflights users on 3/14. 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.
Thu 4/23:25 pm
BOS
- ORF
Nonstop1h 40m
JetBlue
Mon 4/66:00 pm
ORF
- BOS
Nonstop1h 45m
JetBlue
Deal found 3/14![JetBlue logo]()
$216
This Super.com deal was found by Cheapflights users on 3/12. 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.
Sat 4/42:55 pm
BOS
- ORF
Nonstop1h 40m
JetBlue
Mon 4/66:00 pm
ORF
- BOS
Nonstop1h 45m
JetBlue
Deal found 3/12![JetBlue logo]()
$228
This JetBlue deal was found by Cheapflights users on 3/15. 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 4/73:25 pm
BOS
- ORF
Nonstop1h 40m
JetBlue
Thu 4/96:00 pm
ORF
- BOS
Nonstop1h 45m
JetBlue
Deal found 3/15![JetBlue logo]()
$227
This CheapOair deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/133:25 pm
BOS
- ORF
Nonstop1h 40m
Multiple Airlines
Mon 4/206:02 pm
ORF
- BOS
1 stop16h 19m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 3/16. 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.
Tue 4/146:20 am
BOS
- ORF
1 stop3h 40m
Southwest
Wed 4/1511:10 am
ORF
- BOS
1 stop4h 45m
Southwest
Deal found 3/16![Southwest logo]()
$217
This CheapOair deal was found by Cheapflights users on 3/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:50 am
BOS
- ORF
Nonstop1h 42m
Multiple Airlines
Mon 4/206:02 pm
ORF
- BOS
1 stop16h 19m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$229
This JetBlue deal was found by Cheapflights users on 3/12. 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 4/278:50 am
BOS
- ORF
Nonstop1h 42m
JetBlue
Wed 4/2911:24 am
ORF
- BOS
Nonstop1h 38m
JetBlue
Deal found 3/12![JetBlue logo]()
$197
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 March 17, 2026.
Search for one-way flight options from Boston to Chesapeake. Find affordable one-way fares based on user searches. Data last updated March 17, 2026.
This Super.com deal was found by Cheapflights users on 3/12. 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.
Sat 3/289:50 am
BOS
- ORF
1 stop11h 57m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$84
This Super.com deal was found by Cheapflights users on 3/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/319:45 am
BOS
- ORF
1 stop12h 02m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$92
This Super.com deal was found by Cheapflights users on 3/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/133:25 pm
BOS
- ORF
Nonstop1h 40m
JetBlue
Deal found 3/14![JetBlue logo]()
$97
This Super.com deal was found by Cheapflights users on 3/16. 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.
Tue 5/128:50 am
BOS
- ORF
Nonstop1h 42m
JetBlue
Deal found 3/16![JetBlue logo]()
$98
This JetBlue deal was found by Cheapflights users on 3/12. 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 4/148:50 am
BOS
- ORF
Nonstop1h 42m
JetBlue
Deal found 3/12![JetBlue logo]()
$99
This Super.com deal was found by Cheapflights users on 3/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:15 am
BOS
- ORF
Nonstop1h 44m
JetBlue
Deal found 3/13![JetBlue logo]()
$103
This JetBlue deal was found by Cheapflights users on 3/12. 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 7/213:15 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Deal found 3/12![JetBlue logo]()
$104
This Super.com deal was found by Cheapflights users on 3/12. 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.
Thu 3/269:45 am
BOS
- ORF
1 stop12h 02m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:44 am
BOS
- ORF
2 stops26h 27m
Frontier
Deal found 3/17![Frontier logo]()
$106
This Super.com deal was found by Cheapflights users on 3/16. 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.
Thu 4/168:50 am
BOS
- ORF
Nonstop1h 42m
JetBlue
Deal found 3/16![JetBlue logo]()
$107
This Southwest deal was found by Cheapflights users on 3/16. 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 4/156:20 am
BOS
- ORF
1 stop5h 35m
Southwest
Deal found 3/16![Southwest logo]()
$109
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 March 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $197 (JetBlue) |
One-way from | $84 (Super.com) |
Popular in | November |
Cheapest in | June |
Average price | $319 |
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 March 17, 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 - ORF
BOSORF
Boston Logan Intl
Thu 6/4
7:50 pm-11:35 pm
1 stop3h 45m
Norfolk
Sat 6/6
5:40 pm-11:35 pm
1 stop5h 55m
$217
Quickest round-trip
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Wed 7/22
3:15 pm-4:58 pm
Nonstop1h 43m
Norfolk
Sat 7/25
5:53 pm-7:36 pm
Nonstop1h 43m
$222
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Mon 6/22
3:15 pm-4:58 pm
Nonstop1h 43m
Norfolk
Tue 6/30
5:53 pm-7:36 pm
Nonstop1h 43m
$242
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Fri 7/3
3:15 pm-4:58 pm
Nonstop1h 43m
Norfolk
Fri 7/10
5:53 pm-7:36 pm
Nonstop1h 43m
$257
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Wed 8/12
9:00 am-10:55 am
Nonstop1h 55m
Norfolk
Mon 8/17
6:00 am-10:25 am
1 stop4h 25m
$272
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Sat 7/18
3:15 pm-4:58 pm
Nonstop1h 43m
Norfolk
Fri 7/24
5:53 pm-7:36 pm
Nonstop1h 43m
$272
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Sat 6/13
2:40 pm-7:22 pm
1 stop4h 42m
Norfolk
Tue 6/16
6:05 am-10:20 am
1 stop4h 15m
$277
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Sun 9/13
2:25 pm-4:17 pm
Nonstop1h 52m
Norfolk
Sun 9/20
6:00 am-9:54 am
1 stop3h 54m
$297
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Fri 5/1
3:32 pm-11:50 pm
2 stops8h 18m
Norfolk
Mon 5/4
6:15 am-10:18 am
1 stop4h 03m
$302
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Tue 4/7
3:25 pm-5:05 pm
Nonstop1h 40m
Norfolk
Thu 4/9
3:32 pm-12:17 am
1 stop8h 45m
$340
Showing 1-10 of 23 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
How far ahead should I book a flight from Boston to Chesapeake?
Use this chart to determine the optimal time to book a round-trip flight from Boston to Chesapeake. Price data was last updated on March 13, 2026.
To ensure you get the cheapest price possible for a flight from Boston to Chesapeake, you should look to book at least 73 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Boston to Chesapeake?
Currently, July is the cheapest month in which you can book a flight from Boston to Chesapeake (average of $52). Flying from Boston to Chesapeake in March is currently the most expensive (average of $89). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 March 17, 2026.
It’s typically best to fly out from Boston to Chesapeake in the evening. Doing so could potentially save you 38% on the flight price compared to flying at noon, which is usually more expensive.
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 March 14, 2026.
Travelers seeking maximum savings on their Boston to Chesapeake flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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 March 17, 2026.
The most flights from BOS to C6E are scheduled on a Monday (23 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 on average).
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 March 17, 2026.
See what other customers who have flown with Southwest,Delta, andAllegiant Air 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.
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Boston to Chesapeake. 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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Boston to Chesapeake
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Boston to Chesapeake by cabin class
Find flights from Boston to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Boston and Chesapeake flights
Browse other Boston and Chesapeake flight options. Last updated on March 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 March 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Boston to Chesapeake flights
Consider these flights traveling from Boston to Chesapeake.
Top 8 airlines flying from Boston to Chesapeake
Discover the top 8 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 March 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$47 | Average$151 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$48 | Average$77 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$90 | Average$225 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$92 | Average$276 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$106 | Average$165 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$307 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$166 | Average$281 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$356 | FlexibilityNo cancel fee | On-time71% |