$104+ Cheap flights from Chesapeake, VA to Caribbean
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 6/29. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Chesapeake to Caribbean 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.Cheap flight deals from Chesapeake to Caribbean
Keep the following information in mind while searching for Chesapeake to Caribbean flight deals. Data was last updated June 12, 2025.
Round-trip from | $255 (Delta) |
|---|---|
One-way from | $104 (Mytrip) |
Popular in | December |
Cheapest in | July |
Average price | $448 |
Find flight deals from Chesapeake to Caribbean
Cheapest flights from Chesapeake to CaribbeanExplore the most affordable flight options available from Chesapeake to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
Explore the most affordable flight options available from Chesapeake to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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.
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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.
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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.
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.
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.
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Cheapflights Fare Finder
Customize your flight search to find flights from Chesapeake to Caribbean 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, 2025.
Use the filters below to find and compare flights from Chesapeake to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Wed 7/23
1:48 pm-10:23 pm
1 stop8h 35m
San Juan Luis Munoz Marin Intl
Wed 8/6
7:30 am-3:30 pm
1 stop8h 00m
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Thu 7/17
7:39 pm-12:32 am
1 stop28h 53m
San Juan Luis Munoz Marin Intl
Wed 7/30
1:37 am-5:35 pm
1 stop15h 58m
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Sun 8/10
2:03 pm-9:04 am
1 stop19h 01m
San Juan Luis Munoz Marin Intl
Sat 8/23
8:13 pm-9:07 pm
1 stop24h 54m
NorfolkSaint Thomas Island
ORF - STT
ORFSTT
Norfolk
Wed 7/9
5:50 am-12:30 pm
1 stop6h 40m
Saint Thomas Island Cyril E King
Wed 7/16
4:05 pm-10:35 pm
1 stop6h 30m
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Thu 8/21
5:30 am-9:43 pm
1 stop16h 13m
San Juan Luis Munoz Marin Intl
Mon 8/25
5:57 pm-10:49 pm
1 stop28h 52m
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Mon 11/10
7:03 pm-5:05 am
1 stop9h 02m
San Juan Luis Munoz Marin Intl
Thu 11/13
6:30 am-2:43 pm
2 stops9h 13m
NorfolkSaint Thomas Island
ORF - STT
ORFSTT
Norfolk
Mon 7/14
5:50 am-12:30 pm
1 stop6h 40m
Saint Thomas Island Cyril E King
Sat 7/19
10:43 am-8:15 am
1 stop21h 32m
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Wed 9/10
3:45 pm-10:45 pm
1 stop7h 00m
San Juan Luis Munoz Marin Intl
Sun 9/21
5:45 am-5:30 pm
1 stop11h 45m
NorfolkPunta Cana
ORF - PUJ
ORFPUJ
Norfolk
Tue 10/7
6:34 am-2:27 pm
1 stop7h 53m
Punta Cana
Sat 10/11
3:27 pm-10:09 pm
1 stop6h 42m
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Tue 9/16
6:30 am-2:44 pm
1 stop8h 14m
San Juan Luis Munoz Marin Intl
Mon 10/6
1:05 am-9:37 am
2 stops8h 32m
Best time to book a flight from Chesapeake to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Chesapeake with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Chesapeake to Caribbean
What is the cheapest month to book a flight from Chesapeake to Caribbean?
Currently, September is the cheapest month in which you can book a flight from Chesapeake to Caribbean (average of $254). Flying from Chesapeake to Caribbean in June is currently the most expensive (average of $339). 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 C6E to CB?
Find hourly flight availability from Chesapeake to Caribbean. 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, 2025.
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.
Rainfall in Caribbean by month
Plan your trip to Caribbean by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.
Temperature in Caribbean by month
Plan your trip to Caribbean by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated June 12, 2025.
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Chesapeake to Caribbean. 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 Chesapeake to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Chesapeake to Caribbean
Discover the top 7 airlines that operate flights from Chesapeake to Caribbean. 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, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$128 | Average$207 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$166 | Average$430 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$204 | Average$566 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$208 | Average$606 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$234 | Average$524 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$254 | Average$615 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$346 | Average$656 | FlexibilityNo cancel fee | On-time63% |