$96+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
Jul 12 — Jul 191
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 August or July, booked 37 days in advance, depart on a Monday or Friday and return on a Friday
Cheap flight deals from Boston to Chesapeake
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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 June 12, 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 June 12, 2026.
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 8/198:15 am
BOS
- ORF
1 stop6h 15m
Southwest
Wed 8/2612:15 pm
ORF
- BOS
1 stop3h 45m
Southwest
Deal found 6/7![Southwest logo]()
$198
This flygcity.se deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/93:27 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Mon 7/136:00 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 6/7![JetBlue logo]()
$206
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/307:00 am
BOS
- ORF
1 stop4h 03m
American Airlines
Thu 7/95:39 pm
ORF
- BOS
1 stop5h 20m
American Airlines
Deal found 6/11![American Airlines logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:59 pm
BOS
- ORF
Nonstop1h 51m
JetBlue
Sat 10/246:50 pm
ORF
- BOS
Nonstop1h 45m
JetBlue
Deal found 6/11![JetBlue logo]()
$212
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/53:22 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Thu 9/107:05 pm
ORF
- BOS
Nonstop1h 44m
JetBlue
Deal found 6/10![JetBlue logo]()
$217
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/155:45 am
BOS
- ORF
1 stop3h 49m
United Airlines
Thu 8/206:00 am
ORF
- BOS
1 stop6h 47m
United Airlines
Deal found 6/10![United Airlines logo]()
$218
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/45:45 am
BOS
- ORF
1 stop3h 49m
United Airlines
Sat 7/1110:40 am
ORF
- BOS
1 stop6h 44m
United Airlines
Deal found 6/8![United Airlines logo]()
$219
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/116:00 am
BOS
- ORF
1 stop3h 53m
United Airlines
Sun 9/136:02 am
ORF
- BOS
1 stop3h 46m
United Airlines
Deal found 6/8![United Airlines logo]()
$221
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:27 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Mon 7/206:00 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 6/11![JetBlue logo]()
$222
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:45 am
BOS
- ORF
1 stop3h 54m
United Airlines
Tue 7/76:05 am
ORF
- BOS
1 stop5h 47m
United Airlines
Deal found 6/11![United Airlines logo]()
$223
This JetBlue deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 8/253:22 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Wed 8/266:00 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 6/7![JetBlue logo]()
$227
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 June 12, 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 June 12, 2026.
This JetBlue deal was found by Cheapflights users on 6/11. 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.
Tue 8/253:22 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Wed 8/266:00 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 6/11![JetBlue logo]()
$227
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/209:20 am
BOS
- ORF
Nonstop1h 51m
Delta
Sat 8/226:29 pm
ORF
- BOS
1 stop4h 14m
Delta
Deal found 6/10![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:00 pm
BOS
- ORF
1 stop5h 40m
Southwest
Wed 7/1512:40 pm
ORF
- BOS
2 stops10h 45m
Southwest
Deal found 6/11![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:00 am
BOS
- ORF
1 stop3h 40m
Delta
Sat 7/43:15 pm
ORF
- BOS
Nonstop1h 53m
Delta
Deal found 6/11![Delta logo]()
$247
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/289:20 am
BOS
- ORF
Nonstop1h 51m
Delta
Thu 7/307:21 pm
ORF
- BOS
1 stop4h 10m
Delta
Deal found 6/8![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:40 pm
BOS
- ORF
1 stop4h 00m
Southwest
Wed 7/2212:40 pm
ORF
- BOS
2 stops10h 45m
Southwest
Deal found 6/11![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/12:05 pm
BOS
- ORF
Nonstop1h 55m
Delta
Sat 8/86:29 pm
ORF
- BOS
1 stop4h 14m
Delta
Deal found 6/10![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/34:00 pm
BOS
- ORF
Nonstop2h 03m
Delta
Fri 7/107:21 pm
ORF
- BOS
1 stop4h 10m
Delta
Deal found 6/10![Delta logo]()
$287
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:20 am
BOS
- ORF
Nonstop1h 51m
Delta
Mon 7/207:21 pm
ORF
- BOS
1 stop4h 10m
Delta
Deal found 6/11![Delta logo]()
$287
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:00 am
BOS
- ORF
Nonstop1h 55m
Delta
Sun 9/1310:40 am
ORF
- BOS
1 stop5h 46m
Delta
Deal found 6/9![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:05 am
BOS
- ORF
1 stop5h 17m
Delta
Thu 7/2311:55 am
ORF
- BOS
Nonstop1h 53m
Delta
Deal found 6/11![Delta logo]()
$312
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 8/239:20 am
BOS
- ORF
Nonstop1h 51m
Delta
Thu 8/279:26 am
ORF
- BOS
1 stop4h 56m
Delta
Deal found 6/7![Delta logo]()
$342
Last-minute flights from Boston to ChesapeakeDiscover last-minute flight deals from Boston to Chesapeake. Data last updated June 12, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Chesapeake. Data last updated June 12, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
BOS
- ORF
1 stop4h 49m
American Airlines
Wed 7/15:33 am
ORF
- BOS
1 stop6h 17m
American Airlines
Deal found 6/11![American Airlines logo]()
$207
This Expedia deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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.
Thu 7/23:27 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Mon 7/66:00 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 6/10![JetBlue logo]()
$228
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:45 am
BOS
- ORF
1 stop3h 54m
United Airlines
Tue 7/76:05 am
ORF
- BOS
1 stop5h 47m
United Airlines
Deal found 6/11![United Airlines logo]()
$223
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/45:45 am
BOS
- ORF
1 stop3h 49m
United Airlines
Sat 7/1110:40 am
ORF
- BOS
1 stop6h 44m
United Airlines
Deal found 6/8![United Airlines logo]()
$219
This JetBlue deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/73:27 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Mon 7/136:00 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 6/8![JetBlue logo]()
$227
This Expedia deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/83:27 pm
BOS
- ORF
Nonstop1h 43m
Multiple Airlines
Wed 7/159:34 pm
ORF
- BOS
1 stop11h 35m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$234
This flygcity.se deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/93:27 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Mon 7/136:00 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 6/7![JetBlue logo]()
$206
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/103:27 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Tue 7/146:00 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 6/11![JetBlue logo]()
$232
This JetBlue deal was found by Cheapflights users on 6/11. 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 7/103:27 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Wed 7/156:00 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 6/11![JetBlue logo]()
$237
This Cheapflightsfares deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:27 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Mon 7/206:00 pm
ORF
- BOS
Nonstop1h 43m
JetBlue
Deal found 6/9![JetBlue logo]()
$222
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/215:45 am
BOS
- ORF
1 stop3h 54m
United Airlines
Sun 7/266:00 am
ORF
- BOS
1 stop3h 51m
United Airlines
Deal found 6/10![United Airlines logo]()
$231
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 June 12, 2026.
Search for one-way flight options from Boston to Chesapeake. Find affordable one-way fares based on user searches. Data last updated June 12, 2026.
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:50 am
BOS
- ORF
1 stop3h 40m
Southwest
Deal found 6/11![Southwest logo]()
$96
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 10/710:00 am
BOS
- ORF
1 stop6h 05m
Southwest
Deal found 6/7![Southwest logo]()
$102
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:51 pm
BOS
- ORF
1 stop4h 13m
American Airlines
Deal found 6/9![American Airlines logo]()
$104
This Expedia deal was found by Cheapflights users on 6/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1311:05 am
BOS
- ORF
1 stop6h 25m
Frontier
Deal found 6/11![Frontier logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/264:15 pm
BOS
- ORF
Nonstop1h 55m
JetBlue
Deal found 6/9![JetBlue logo]()
$108
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/161:30 pm
BOS
- ORF
2 stops10h 06m
United Airlines
Deal found 6/8![United Airlines logo]()
$109
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 11/248:45 am
BOS
- ORF
1 stop7h 35m
Southwest
Deal found 6/10![Southwest logo]()
$111
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/203:27 pm
BOS
- ORF
Nonstop1h 43m
JetBlue
Deal found 6/10![JetBlue logo]()
$113
This Delta deal was found by Cheapflights users on 6/12. 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.
Wed 8/59:20 am
BOS
- ORF
Nonstop1h 51m
Delta
Deal found 6/12![Delta logo]()
$114
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/116:05 pm
BOS
- ORF
1 stop5h 39m
United Airlines
Deal found 6/8![United Airlines logo]()
$116
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:00 am
BOS
- ORF
1 stop6h 05m
Southwest
Deal found 6/8![Southwest logo]()
$117
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 June 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $198 (Southwest) |
One-way from | $96 (Southwest) |
Popular in | November |
Cheapest in | August |
Average price | $274 |
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 June 12, 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
Quickest round-trip
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Tue 8/25
3:22 pm-5:05 pm
Nonstop1h 43m
Norfolk
Wed 8/26
6:00 pm-7:43 pm
Nonstop1h 43m
$227
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Thu 8/20
9:20 am-11:11 am
Nonstop1h 51m
Norfolk
Sat 8/22
6:29 pm-10:43 pm
1 stop4h 14m
$247
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Fri 7/3
6:00 am-9:40 am
1 stop3h 40m
Norfolk
Sat 7/4
3:15 pm-5:08 pm
Nonstop1h 53m
$247
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Tue 7/28
9:20 am-11:11 am
Nonstop1h 51m
Norfolk
Thu 7/30
7:21 pm-11:31 pm
1 stop4h 10m
$247
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Sat 8/1
2:05 pm-4:00 pm
Nonstop1h 55m
Norfolk
Sat 8/8
6:29 pm-10:43 pm
1 stop4h 14m
$277
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Fri 7/3
4:00 pm-6:03 pm
Nonstop2h 03m
Norfolk
Fri 7/10
7:21 pm-11:31 pm
1 stop4h 10m
$287
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Wed 7/15
9:20 am-11:11 am
Nonstop1h 51m
Norfolk
Mon 7/20
7:21 pm-11:31 pm
1 stop4h 10m
$287
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Tue 7/14
5:00 pm-10:40 pm
1 stop5h 40m
Norfolk
Wed 7/15
12:40 pm-11:25 pm
2 stops10h 45m
$296
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Thu 9/10
9:00 am-10:55 am
Nonstop1h 55m
Norfolk
Sun 9/13
10:40 am-4:26 pm
1 stop5h 46m
$297
BostonNorfolk
BOS - ORF
BOSORF
Boston Logan Intl
Tue 7/21
6:40 pm-10:40 pm
1 stop4h 00m
Norfolk
Wed 7/22
12:40 pm-11:25 pm
2 stops10h 45m
$307
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 June 12, 2026.
It’s typically best to fly out from Boston to Chesapeake in the evening. Doing so could potentially save you 42% 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 June 12, 2026.
The most flights from BOS to C6E are scheduled on a Thursday (17 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?
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 June 8, 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 evenings 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 June 12, 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.
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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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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 June 12, 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 June 12, 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 7 airlines flying from Boston to Chesapeake
Discover the top 7 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 June 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$49 | Average$76 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$83 | Average$295 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$106 | Average$188 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$106 | Average$261 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$321 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$166 | Average$276 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$379 | FlexibilityNo cancel fee | On-time71% |