When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 35 days in advance, which can save you up to 76% on flights from Chesapeake to Puerto Rico compared to booking the week you need them. Waiting 35 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $301. For sooner than that we have options available in the next 3 days from $578.
September can be a great time to fly to Puerto Rico from Chesapeake with a flight ticket averaging about $449. Cheapflights users have found deals in the month of September for as cheap as $167. The most expensive prices can be found in the month of December.
When flying from Chesapeake to Puerto Rico, 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
$243 - $353
Route
Depart
Return
Price
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
火 6/4
2 stops28h 55m
San Juan Luis Munoz Marin Intl
月 6/24
1 stop6h 01m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
木 6/6
1 stop12h 33m
San Juan Luis Munoz Marin Intl
月 6/10
2 stops32h 05m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
木 5/16
1 stop6h 19m
San Juan Luis Munoz Marin Intl
水 5/22
1 stop12h 38m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
火 6/25
1 stop9h 59m
San Juan Luis Munoz Marin Intl
火 7/2
Nonstop3h 49m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
水 5/15
2 stops16h 00m
San Juan Luis Munoz Marin Intl
土 5/18
2 stops15h 57m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
火 7/30
Nonstop3h 34m
San Juan Luis Munoz Marin Intl
火 8/6
Nonstop3h 38m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
日 5/12
1 stop11h 47m
San Juan Luis Munoz Marin Intl
月 5/20
1 stop14h 04m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
火 5/14
1 stop7h 45m
San Juan Luis Munoz Marin Intl
火 5/14
1 stop7h 53m
NorfolkSan Juan Luis Munoz Marin Intl
ORF - SJU
ORFSJU
Norfolk
日 5/12
1 stop7h 44m
San Juan Luis Munoz Marin Intl
水 5/22
1 stop9h 39m
No data available for this route at this time. Please check back soon.
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Cheapflights makes it easy to find Chesapeake to Puerto Rico flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
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Yes, we can. To see specific flights from Chesapeake to Puerto Rico with no change fees, users can toggle flexible booking options after using the search form above to find flights.
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