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$97+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
avr. 7 — avr. 141
lun. 4/7
lun. 4/14
1 adult, Economy
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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 avril 2, 2025.

Round-trip from

$209
(CheapOair)

One-way from

$97
(Cheapflightsfares)

Popular in

December

Cheapest in

July

Average price

$408
From Chesapeake to Caribbean
Search Deals
One-way flight from Chesapeake to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find 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 avril 2, 2025.

This CheapOair deal was found by Cheapflights users on 3/31. 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.
mer. 4/166:13 pmORF - STT
1 stop15h 47mSpirit Airlines
ven. 4/2511:05 amSTT - ORF
1 stop13h 14mSpirit Airlines
Deal found 3/31$209
This CheapOair deal was found by Cheapflights users on 3/31. 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.
lun. 4/146:00 amORF - SJU
1 stop11h 33mSpirit Airlines
ven. 4/186:38 pmSJU - ORF
1 stop5h 41mSpirit Airlines
Deal found 3/31$238
This CheapOair deal was found by Cheapflights users on 4/1. 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.
ven. 4/185:37 pmORF - SJU
1 stop8h 13mMultiple Airlines
sam. 4/266:38 pmSJU - ORF
1 stop5h 41mMultiple Airlines
Deal found 4/1$239
This Delta deal was found by Cheapflights users on 4/1. 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.
mar. 9/169:45 amORF - SJU
1 stop6h 23mDelta
mar. 9/231:13 pmSJU - ORF
1 stop9h 42mDelta
Deal found 4/1$245
This Mytrip deal was found by Cheapflights users on 4/1. 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.
jeu. 5/153:11 pmORF - STT
1 stop18h 46mMultiple Airlines
dim. 5/184:35 pmSTT - ORF
1 stop21h 53mMultiple Airlines
Deal found 4/1$263
This United Airlines deal was found by Cheapflights users on 4/1. 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.
mar. 5/66:27 amORF - SJU
1 stop6h 07mUnited Airlines
sam. 5/101:05 amSJU - ORF
2 stops13h 26mUnited Airlines
Deal found 4/1$263
This American Airlines deal was found by Cheapflights users on 4/1. 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.
mar. 9/165:50 amORF - SJU
2 stops10h 30mAmerican Airlines
mar. 10/712:00 pmSJU - ORF
2 stops11h 03mAmerican Airlines
Deal found 4/1$265
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
mer. 4/166:00 amORF - PUJ
1 stop8h 13mSpirit Airlines
jeu. 4/2412:39 pmPUJ - ORF
1 stop7h 22mSpirit Airlines
Deal found 3/31$275
This Frontier deal was found by Cheapflights users on 4/1. 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.
jeu. 4/175:41 pmORF - SJU
1 stop8h 09mFrontier
lun. 4/215:45 amSJU - ORF
1 stop11h 13mFrontier
Deal found 4/1$316
This CheapOair deal was found by Cheapflights users on 4/1. 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.
lun. 4/216:00 amORF - MBJ
1 stop5h 55mSpirit Airlines
mer. 5/1412:07 pmMBJ - ORF
1 stop25h 09mSpirit Airlines
Deal found 4/1$336
This Priceline deal was found by Cheapflights users on 4/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 4/256:00 amORF - SDQ
1 stop9h 49mSpirit Airlines
lun. 5/54:44 pmSDQ - ORF
1 stop7h 35mSpirit Airlines
Deal found 4/1$375
This Mytrip deal was found by Cheapflights users on 3/31. 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.
ven. 5/26:13 pmORF - MBJ
1 stop17h 42mMultiple Airlines
lun. 5/53:05 pmMBJ - ORF
1 stop8h 14mMultiple Airlines
Deal found 3/31$381

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 avril 2, 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

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

mer. 4/16

6:13 pm-10:00 am

1 stop15h 47m

Saint Thomas Island Cyril E King

ven. 4/25

11:05 am-12:19 am

1 stop13h 14m

$209

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

lun. 4/14

6:00 am-5:33 pm

1 stop11h 33m

San Juan Luis Munoz Marin Intl

ven. 4/18

6:38 pm-12:19 am

1 stop5h 41m

$238

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

ven. 4/18

5:37 pm-1:50 am

1 stop8h 13m

San Juan Luis Munoz Marin Intl

sam. 4/26

6:38 pm-12:19 am

1 stop5h 41m

$239

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mar. 9/16

9:45 am-4:08 pm

1 stop6h 23m

San Juan Luis Munoz Marin Intl

mar. 9/23

1:13 pm-10:55 pm

1 stop9h 42m

$245

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mar. 5/6

6:27 am-12:34 pm

1 stop6h 07m

San Juan Luis Munoz Marin Intl

sam. 5/10

1:05 am-2:31 pm

2 stops13h 26m

$263

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

jeu. 5/15

3:11 pm-9:57 am

1 stop18h 46m

Saint Thomas Island Cyril E King

dim. 5/18

4:35 pm-2:28 pm

1 stop21h 53m

$263

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mar. 9/16

5:50 am-4:20 pm

2 stops10h 30m

San Juan Luis Munoz Marin Intl

mar. 10/7

12:00 pm-11:03 pm

2 stops11h 03m

$265

NorfolkPunta Cana

ORF - PUJ

ORFPUJ

Norfolk

mer. 4/16

6:00 am-2:13 pm

1 stop8h 13m

Punta Cana

jeu. 4/24

12:39 pm-8:01 pm

1 stop7h 22m

$275

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

jeu. 4/17

5:41 pm-1:50 am

1 stop8h 09m

San Juan Luis Munoz Marin Intl

lun. 4/21

5:45 am-4:58 pm

1 stop11h 13m

$316

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

lun. 4/21

6:00 am-10:55 am

1 stop5h 55m

Montego Bay Sangster Intl

mer. 5/14

12:07 pm-2:16 pm

1 stop25h 09m

$336

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 58 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, 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 December is currently the most expensive (average of $336). 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 avril 2, 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 avril 2, 2025.
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Copa Airlines
7.6
Good
1,400 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
LATAM Airlines
7.5
Good
1,754 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,615 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $97. Users have also found prices from $123 and $126 on Delta 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 - Montego Bay Sangster Intl or Norfolk - Punta Cana.

  • 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, 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 December is currently the most expensive (average of $336). 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

Browse thousands of different options on Cheapflights for your next trip

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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 avril 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$128Average$409FlexibilityNo cancel feeOn-time65%
FrontierCheapest$134Average$295FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$625FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$533FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$256Average$578FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$257Average$622FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$349Average$610FlexibilityNo cancel feeOn-time63%

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