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$123+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Round-trip from

$245
(Delta)

One-way from

$123
(American Airlines)

Popular in

December

Cheapest in

July

Average price

$459
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 ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 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 April 24, 2025.

This Delta deal was found by Cheapflights users on 4/23. 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.
Tue 9/167:00 amORF - SJU
1 stop9h 18mDelta
Tue 9/232:28 pmSJU - ORF
1 stop9h 33mDelta
Deal found 4/23$245
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Wed 5/218:24 pmORF - SJU
1 stop14h 46mAmerican Airlines
Wed 5/286:10 amSJU - ORF
2 stops8h 34mAmerican Airlines
Deal found 4/23$251
This CheapOair deal was found by Cheapflights users on 4/23. 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.
Sat 5/173:11 pmORF - SJU
1 stop27h 56mSpirit Airlines
Fri 5/231:59 amSJU - ORF
1 stop8h 30mSpirit Airlines
Deal found 4/23$287
This Frontier deal was found by Cheapflights users on 4/22. 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 5/411:21 amORF - SJU
1 stop12h 44mFrontier
Wed 5/73:56 amSJU - ORF
1 stop6h 35mFrontier
Deal found 4/22$298
This American Airlines deal was found by Cheapflights users on 4/24. 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.
Fri 8/227:00 amORF - STX
1 stop6h 10mAmerican Airlines
Sun 8/243:50 pmSTX - ORF
2 stops19h 50mAmerican Airlines
Deal found 4/24$309
This Booking.com deal was found by Cheapflights users on 4/23. 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 5/1912:13 pmORF - SJU
1 stop12h 41mMultiple Airlines
Mon 5/2610:00 amSJU - ORF
1 stop28h 33mMultiple Airlines
Deal found 4/23$316
This CheapOair deal was found by Cheapflights users on 4/23. 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.
Sat 5/1712:13 pmORF - STT
1 stop27h 17mSpirit Airlines
Fri 5/231:21 pmSTT - ORF
1 stop21h 08mSpirit Airlines
Deal found 4/23$333
This United Airlines deal was found by Cheapflights users on 4/23. 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 9/176:30 amORF - SJU
1 stop8h 14mUnited Airlines
Mon 9/291:05 amSJU - ORF
2 stops13h 35mUnited Airlines
Deal found 4/23$335
This Southwest deal was found by Cheapflights users on 4/23. 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.
Sun 5/112:25 pmORF - SJU
1 stop10h 15mSouthwest
Fri 5/167:40 amSJU - ORF
2 stops11h 05mSouthwest
Deal found 4/23$360
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Sat 9/66:19 pmORF - PLS
2 stops17h 42mAmerican Airlines
Sat 9/133:50 pmPLS - ORF
1 stop7h 50mAmerican Airlines
Deal found 4/21$389
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Thu 9/46:49 pmORF - STT
2 stops18h 01mAmerican Airlines
Wed 9/101:50 pmSTT - ORF
2 stops19h 35mAmerican Airlines
Deal found 4/23$391
This Mytrip deal was found by Cheapflights users on 4/23. 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.
Fri 6/204:11 pmORF - PUJ
1 stop23h 48mSpirit Airlines
Tue 6/243:23 pmPUJ - ORF
1 stop27h 14mSpirit Airlines
Deal found 4/23$402

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 April 24, 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

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 9/16

7:00 am-4:18 pm

1 stop9h 18m

San Juan Luis Munoz Marin Intl

Tue 9/23

2:28 pm-12:01 am

1 stop9h 33m

$245

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 5/21

8:24 pm-11:10 am

1 stop14h 46m

San Juan Luis Munoz Marin Intl

Wed 5/28

6:10 am-2:44 pm

2 stops8h 34m

$251

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 5/17

3:11 pm-7:07 pm

1 stop27h 56m

San Juan Luis Munoz Marin Intl

Fri 5/23

1:59 am-10:29 am

1 stop8h 30m

$287

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sun 5/4

11:21 am-12:05 am

1 stop12h 44m

San Juan Luis Munoz Marin Intl

Wed 5/7

3:56 am-10:31 am

1 stop6h 35m

$298

NorfolkChristiansted

ORF - STX

ORFSTX

Norfolk

Fri 8/22

7:00 am-1:10 pm

1 stop6h 10m

Christiansted Henry Rohlsen

Sun 8/24

3:50 pm-11:40 am

2 stops19h 50m

$309

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 5/19

12:13 pm-12:54 am

1 stop12h 41m

San Juan Luis Munoz Marin Intl

Mon 5/26

10:00 am-2:33 pm

1 stop28h 33m

$316

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Sat 5/17

12:13 pm-3:30 pm

1 stop27h 17m

Saint Thomas Island Cyril E King

Fri 5/23

1:21 pm-10:29 am

1 stop21h 08m

$333

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 9/17

6:30 am-2:44 pm

1 stop8h 14m

San Juan Luis Munoz Marin Intl

Mon 9/29

1:05 am-2:40 pm

2 stops13h 35m

$335

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sun 5/11

2:25 pm-12:40 am

1 stop10h 15m

San Juan Luis Munoz Marin Intl

Fri 5/16

7:40 am-6:45 pm

2 stops11h 05m

$360

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Thu 9/4

7:09 pm-12:50 pm

2 stops17h 41m

Saint Thomas Island Cyril E King

Wed 9/10

1:50 pm-11:29 pm

1 stop9h 39m

$391

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 53 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 April 24, 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 April 24, 2025.
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Copa Airlines
7.6
Good
1,411 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
LATAM Airlines
7.5
Good
1,765 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,685 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 American Airlines. According to our data, you can fly for as low as $123. Users have also found prices from $128 and $149 on Spirit Airlines and Frontier, respectively.

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

    The most popular route from Chesapeake to Caribbean is Norfolk - Montego Bay Sangster Intl. You may also consider Norfolk - San Juan Luis Munoz Marin Intl 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, 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

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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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$128Average$423FlexibilityNo cancel feeOn-time65%
FrontierCheapest$130Average$231FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$611FlexibilityNo cancel feeOn-time69%
DeltaCheapest$233Average$519FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$255Average$618FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$255Average$579FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$359Average$616FlexibilityNo cancel feeOn-time63%

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