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$98+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$190
(CheapOair)

One-way from

$98
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$470
From Chesapeake to Caribbean
Search Deals
One-way flight from Chesapeake to Caribbean
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This CheapOair deal was found by Cheapflights users on 7/29. 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.
Tue 11/118:01 amORF - STT
1 stop6h 10mSpirit Airlines
Tue 11/184:06 pmSTT - ORF
1 stop9h 01mSpirit Airlines
Deal found 7/29$190
This CheapOair deal was found by Cheapflights users on 7/28. 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.
Thu 10/235:24 amORF - SJU
1 stop5h 47mMultiple Airlines
Sun 10/269:07 amSJU - ORF
1 stop6h 15mMultiple Airlines
Deal found 7/28$204
This Delta deal was found by Cheapflights users on 7/28. 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 9/167:10 amORF - SJU
1 stop9h 07mDelta
Tue 9/237:00 amSJU - ORF
1 stop10h 39mDelta
Deal found 7/28$205
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Tue 9/210:30 amORF - SJU
2 stops13h 27mUnited Airlines
Tue 10/71:05 amSJU - ORF
2 stops8h 32mUnited Airlines
Deal found 7/30$216
This Cheapflightsfares deal was found by Cheapflights users on 7/27. 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.
Thu 9/115:12 pmORF - SJU
1 stop6h 47mFrontier
Thu 9/259:07 amSJU - ORF
1 stop7h 05mFrontier
Deal found 7/27$226
This CheapOair deal was found by Cheapflights users on 7/29. 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.
Mon 8/255:20 pmORF - SJU
1 stop6h 37mSpirit Airlines
Thu 9/411:59 amSJU - ORF
1 stop10h 49mSpirit Airlines
Deal found 7/29$228
This Southwest deal was found by Cheapflights users on 7/30. 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.
Wed 9/172:20 pmORF - SJU
1 stop8h 10mSouthwest
Sun 9/215:05 amSJU - ORF
1 stop9h 20mSouthwest
Deal found 7/30$245
This CheapOair deal was found by Cheapflights users on 7/29. 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 9/135:45 amORF - MBJ
1 stop6h 20mSpirit Airlines
Thu 9/1812:10 pmMBJ - ORF
1 stop9h 38mSpirit Airlines
Deal found 7/29$283
This American Airlines deal was found by Cheapflights users on 7/30. 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 9/175:30 amORF - SJU
2 stops10h 22mAmerican Airlines
Tue 9/3012:01 pmSJU - ORF
2 stops10h 36mAmerican Airlines
Deal found 7/30$284
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Wed 8/135:30 amORF - PUJ
1 stop9h 30mSpirit Airlines
Sat 8/164:05 pmPUJ - ORF
1 stop6h 29mSpirit Airlines
Deal found 7/30$285
This American Airlines deal was found by Cheapflights users on 7/29. 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 9/15:00 amORF - PUJ
1 stop9h 10mAmerican Airlines
Thu 9/41:35 pmPUJ - ORF
1 stop10h 24mAmerican Airlines
Deal found 7/29$313
This FlightHub deal was found by Cheapflights users on 7/30. 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.
Thu 9/45:45 amORF - SDQ
1 stop10h 15mSpirit Airlines
Sun 9/71:20 pmSDQ - ORF
1 stop27h 23mSpirit Airlines
Deal found 7/30$345

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 July 30, 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

Thu 10/23

5:24 am-11:11 am

1 stop5h 47m

San Juan Luis Munoz Marin Intl

Sun 10/26

9:07 am-3:22 pm

1 stop6h 15m

$204

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 9/16

7:10 am-4:17 pm

1 stop9h 07m

San Juan Luis Munoz Marin Intl

Tue 9/23

7:00 am-5:39 pm

1 stop10h 39m

$205

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 9/2

10:30 am-11:57 pm

2 stops13h 27m

San Juan Luis Munoz Marin Intl

Tue 10/7

1:05 am-9:37 am

2 stops8h 32m

$216

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 9/11

5:12 pm-11:59 pm

1 stop6h 47m

San Juan Luis Munoz Marin Intl

Thu 9/25

9:07 am-4:12 pm

1 stop7h 05m

$226

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 8/25

5:20 pm-11:57 pm

1 stop6h 37m

San Juan Luis Munoz Marin Intl

Thu 9/4

11:59 am-10:48 pm

1 stop10h 49m

$228

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 9/17

2:20 pm-10:30 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Sun 9/21

5:05 am-2:25 pm

1 stop9h 20m

$245

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Thu 8/28

5:30 am-11:13 am

1 stop5h 43m

Saint Thomas Island Cyril E King

Tue 9/2

12:18 pm-10:34 pm

1 stop10h 16m

$254

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sat 9/13

5:45 am-11:05 am

1 stop6h 20m

Montego Bay Sangster Intl

Thu 9/18

12:10 pm-10:48 pm

1 stop9h 38m

$283

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 9/17

5:30 am-3:52 pm

2 stops10h 22m

San Juan Luis Munoz Marin Intl

Tue 9/30

12:01 pm-10:37 pm

2 stops10h 36m

$284

NorfolkPunta Cana

ORF - PUJ

ORFPUJ

Norfolk

Wed 8/13

5:30 am-3:00 pm

1 stop9h 30m

Punta Cana

Sat 8/16

4:05 pm-10:34 pm

1 stop6h 29m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 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 July 30, 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.

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 July 30, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Copa 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
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Copa Airlines
7.5
Good
1,493 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $98. Users have also found prices from $118 and $145 on Frontier 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 - Oranjestad Reina Beatrix or Norfolk - Montego Bay Sangster Intl.

  • 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 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.

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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$295FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$108Average$427FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$204Average$553FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$603FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$526FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$254Average$610FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$290Average$649FlexibilityNo cancel feeOn-time63%

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