To save on the cost of your flight from Chesapeake to Caribbean, book at least 40 days before your planned departure. Booking around this time can save you about 97% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $307 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $590.
Flights from Chesapeake to Caribbean lean towards being more expensive in December. Prices are generally better when you fly from Chesapeake to Caribbean in October, with the cheapest ticket starting at $231.
When flying from Chesapeake to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$150 - $391
Route
Depart
Return
Price
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
Sat 5/11
1 stop9h 36m
San Juan Luis Munoz Marin Intl
Sat 5/18
1 stop10h 49m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
Sat 5/25
1 stop6h 03m
San Juan Luis Munoz Marin Intl
Sun 6/2
1 stop10h 38m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
Tue 5/28
1 stop10h 09m
San Juan Luis Munoz Marin Intl
Tue 6/4
1 stop15h 38m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
Tue 5/28
1 stop10h 09m
San Juan Luis Munoz Marin Intl
Tue 6/4
Nonstop3h 49m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
Fri 5/24
1 stop20h 41m
San Juan Luis Munoz Marin Intl
Sun 6/2
Nonstop3h 49m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
Thu 6/6
Nonstop3h 31m
San Juan Luis Munoz Marin Intl
Sun 6/9
Nonstop3h 49m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
Thu 9/5
2 stops19h 50m
San Juan Luis Munoz Marin Intl
Thu 9/12
2 stops17h 45m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
Thu 8/8
1 stop10h 55m
San Juan Luis Munoz Marin Intl
Tue 8/13
1 stop6h 46m
NorfolkSantiago de los Caballeros
ORF - STI
ORFSTI
Norfolk
Sat 5/11
1 stop9h 31m
Santiago de los Caballeros
Wed 5/15
1 stop7h 03m
No data available for this route at this time. Please check back soon.
Crew
Overall
Comfort
Boarding
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Crew
Overall
Comfort
Boarding
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Crew
Overall
Comfort
Boarding
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Crew
Overall
Comfort
Boarding
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Crew
Overall
Comfort
Boarding
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Crew
Overall
Comfort
Boarding
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Cheapflights helps you search for flights from Chesapeake to Caribbean via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chesapeake to Caribbean.
Certainly. Search results for flights to Caribbean from Chesapeake shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Of course! You can now track prices for flights from Chesapeake to Caribbean and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.