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$125+ 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 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap flight deals from Chesapeake to Caribbean

Cheapest flights from Chesapeake to Caribbean
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 December 15, 2025.

This Frontier deal was found by Cheapflights users on 12/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/222:04 pmORF - SJU
1 stop8h 34mFrontier
Thu 1/86:15 amSJU - ORF
1 stop8h 19mFrontier
Deal found 12/14$284
This Orbitz deal was found by Cheapflights users on 12/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/233:11 pmORF - SJU
1 stop10h 39mMultiple Airlines
Wed 1/71:55 amSJU - ORF
2 stops17h 43mMultiple Airlines
Deal found 12/13$351
This Frontier deal was found by Cheapflights users on 12/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/213:09 pmORF - SJU
1 stop10h 41mFrontier
Thu 1/86:15 amSJU - ORF
1 stop8h 19mFrontier
Deal found 12/13$353
This Frontier deal was found by Cheapflights users on 12/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/203:01 pmORF - SJU
1 stop10h 49mFrontier
Sun 12/216:00 amSJU - ORF
1 stop9h 14mFrontier
Deal found 12/13$354
This Frontier deal was found by Cheapflights users on 12/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/203:01 pmORF - SJU
1 stop10h 49mFrontier
Thu 1/86:15 amSJU - ORF
1 stop8h 19mFrontier
Deal found 12/13$373
This Delta deal was found by Cheapflights users on 12/12. 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.
Mon 12/155:15 amORF - MBJ
1 stop8h 58mDelta
Fri 12/193:38 pmMBJ - ORF
1 stop6h 51mDelta
Deal found 12/12$377
This Booking.com deal was found by Cheapflights users on 12/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:38 amORF - SJU
1 stop14h 38mMultiple Airlines
Mon 12/229:37 pmSJU - ORF
1 stop17h 39mMultiple Airlines
Deal found 12/14$379
This American Airlines deal was found by Cheapflights users on 12/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:51 amORF - MBJ
2 stops9h 58mAmerican Airlines
Fri 12/194:11 pmMBJ - ORF
1 stop8h 48mAmerican Airlines
Deal found 12/14$382
This Booking.com deal was found by Cheapflights users on 12/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/292:04 pmORF - SJU
1 stop8h 34mFrontier
Sat 1/106:18 pmSJU - ORF
1 stop20h 16mFrontier
Deal found 12/12$382
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:11 pmORF - SJU
1 stop22h 49mMultiple Airlines
Sun 12/217:35 amSJU - ORF
1 stop7h 31mMultiple Airlines
Deal found 12/13$384
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:05 amORF - SJU
2 stops15h 17mUnited Airlines
Wed 12/245:50 pmSJU - ORF
1 stop6h 51mUnited Airlines
Deal found 12/14$386
This Frontier deal was found by Cheapflights users on 12/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/213:09 pmORF - SJU
1 stop10h 41mFrontier
Sat 1/103:55 amSJU - ORF
1 stop10h 39mFrontier
Deal found 12/13$387

Find flight deals from Chesapeake to Caribbean

Keep the following information in mind while searching for Chesapeake to Caribbean flight deals. Data was last updated December 15, 2025.

Round-trip from

$250
(Kiwi.com)

One-way from

$125
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$583
From Chesapeake to Caribbean
Search Deals
One-way flight from Chesapeake to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search 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 December 15, 2025.
Use the filters below to find and compare flights from Chesapeake to Caribbean that are best for you.

Fly from

Chesapeake

Fly to

Caribbean

Route

Depart

Return

Price

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Thu 1/29

7:33 pm-2:10 pm

1 stop17h 37m

Simpson Bay Princess Juliana

Thu 2/5

3:15 pm-6:38 pm

1 stop28h 23m

$250

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Sat 1/24

5:30 pm-3:05 pm

2 stops20h 35m

Saint Thomas Island Cyril E King

Fri 1/30

3:57 pm-9:50 pm

1 stop6h 53m

$276

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sun 2/1

9:37 pm-9:47 am

1 stop11h 10m

San Juan Luis Munoz Marin Intl

Sun 2/8

6:00 am-8:52 pm

1 stop15h 52m

$283

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Mon 2/2

6:45 am-2:52 pm

1 stop7h 07m

Saint Thomas Island Cyril E King

Fri 2/6

3:57 pm-9:50 pm

1 stop6h 53m

$284

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 1/13

5:20 am-1:05 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:27 pm-12:16 am

1 stop6h 49m

$285

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Fri 2/6

7:01 am-4:50 pm

1 stop8h 49m

San Juan Luis Munoz Marin Intl

Thu 2/12

3:55 pm-10:23 pm

1 stop7h 28m

$285

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 2/2

6:45 am-3:26 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

Sat 2/7

2:59 am-6:38 pm

2 stops16h 39m

$287

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 2/5

6:45 am-7:26 pm

2 stops11h 41m

San Juan Luis Munoz Marin Intl

Sat 2/7

8:00 am-8:15 pm

1 stop13h 15m

$287

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 2/5

6:45 am-7:26 pm

2 stops11h 41m

San Juan Luis Munoz Marin Intl

Wed 2/11

6:00 am-6:25 pm

1 stop13h 25m

$287

NorfolkSanto Domingo

ORF - SDQ

ORFSDQ

Norfolk

Mon 2/2

7:33 pm-2:27 pm

1 stop17h 54m

Santo Domingo Las Americas

Sat 2/7

3:32 pm-6:38 pm

1 stop28h 06m

$292

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 60 results
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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.
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 Chesapeake to Caribbean

What is the cheapest month to book a flight from Chesapeake to Caribbean?

Currently, May is the cheapest month in which you can book a flight from Chesapeake to Caribbean (average of $113). Flying from Chesapeake to Caribbean in June is currently the most expensive (average of $208). 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 December 15, 2025.

One of the essential ways to save on airfare from Chesapeake to Caribbean is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 21% on airfare.

What is the cheapest day to fly from Chesapeake to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chesapeake to Caribbean flight should consider departing on Tuesday at noon when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 December 15, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Chesapeake to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,007 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,092 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,052 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,185 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Chesapeake to Caribbean?

    Airlines like Spirit Airlines, Delta, and American Airlines fly from Chesapeake to Caribbean in about 6h 45m. The time it takes to get you to your destination can typically vary by up to 10h 52m. Airlines will cover a distance of 1416 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chesapeake to Caribbean one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $84. Users have also found prices from $105 and $112 on Spirit Airlines and American Airlines, respectively.

  • What are the most popular routes from Chesapeake to Caribbean?

    The most popular route from Chesapeake to Caribbean is Norfolk - San Juan Luis Munoz Marin Intl. You may also consider Norfolk - Punta Cana or Norfolk - Saint Thomas Island Cyril E King.

  • Can I find deals for flights from Chesapeake to Caribbean that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Caribbean.

  • Can I find deals for business class flights from Chesapeake to Caribbean?

    Yes. Cheapflights offers flight deals from Chesapeake to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chesapeake to Caribbean?

    Currently, May is the cheapest month in which you can book a flight from Chesapeake to Caribbean (average of $113). Flying from Chesapeake to Caribbean in June is currently the most expensive (average of $208). 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.

See more FAQs

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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.
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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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$292FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$90Average$394FlexibilityNo cancel feeOn-time65%
DeltaCheapest$212Average$526FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$225Average$580FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$225Average$597FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$250Average$627FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$256Average$550FlexibilityNo cancel feeOn-time62%

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