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$91+ 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 1/2. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
nov. 28 — dic. 51
vie. 11/28
vie. 12/5
1 adult, Economy
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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 octubre 29, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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.
lun. 11/249:26 pmORF - STT
1 stop16h 04mSpirit Airlines
mié. 12/33:25 pmSTT - ORF
1 stop6h 06mSpirit Airlines
Deal found 10/27$249
This Expedia deal was found by Cheapflights users on 10/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/209:26 pmORF - STT
1 stop16h 04mSpirit Airlines
lun. 11/243:25 pmSTT - ORF
1 stop6h 06mSpirit Airlines
Deal found 10/27$260
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/277:18 pmORF - SJU
1 stop27h 26mMultiple Airlines
sáb. 12/68:00 amSJU - ORF
1 stop15h 03mMultiple Airlines
Deal found 10/28$269
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/269:26 pmORF - SJU
1 stop22h 46mMultiple Airlines
sáb. 12/68:00 amSJU - ORF
1 stop15h 03mMultiple Airlines
Deal found 10/28$273
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/218:02 pmORF - SJU
1 stop26h 27mMultiple Airlines
dom. 11/233:59 amSJU - ORF
1 stop6h 44mMultiple Airlines
Deal found 10/28$278
This American Airlines deal was found by Cheapflights users on 10/29. 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.
vie. 11/146:00 amORF - SJU
2 stops10h 05mAmerican Airlines
mié. 11/196:25 amSJU - ORF
1 stop14h 35mAmerican Airlines
Deal found 10/29$290
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/239:26 pmORF - SJU
1 stop13h 12mMultiple Airlines
lun. 11/243:59 amSJU - ORF
1 stop17h 32mMultiple Airlines
Deal found 10/28$294
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/132:00 pmORF - SJU
1 stop11h 54mFrontier
sáb. 11/153:59 amSJU - ORF
1 stop9h 17mFrontier
Deal found 10/29$296
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/219:26 pmORF - SJU
1 stop12h 20mMultiple Airlines
sáb. 11/223:59 amSJU - ORF
1 stop10h 16mMultiple Airlines
Deal found 10/28$299
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/269:26 pmORF - SJU
1 stop22h 46mMultiple Airlines
mié. 12/39:15 amSJU - ORF
2 stops47h 28mMultiple Airlines
Deal found 10/29$300
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/27:00 amORF - SJU
1 stop9h 20mDelta
mié. 12/101:57 pmSJU - ORF
1 stop11h 35mDelta
Deal found 10/27$301
This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/88:11 pmORF - MBJ
1 stop15h 59mSpirit Airlines
jue. 12/111:05 pmMBJ - ORF
1 stop6h 11mSpirit Airlines
Deal found 10/28$342

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 octubre 29, 2025.

Round-trip from

$245
(American Airlines)

One-way from

$91
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$361
From Chesapeake to Caribbean
Search Deals
One-way flight from Chesapeake to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 octubre 29, 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

mar. 3/3

5:30 am-5:12 pm

1 stop10h 42m

San Juan Luis Munoz Marin Intl

jue. 3/5

6:15 am-2:00 pm

1 stop8h 45m

$247

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

lun. 1/26

5:20 am-1:05 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

vie. 1/30

6:27 pm-12:16 am

1 stop6h 49m

$247

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

jue. 1/8

7:00 am-4:49 pm

1 stop8h 49m

San Juan Luis Munoz Marin Intl

vie. 1/16

2:15 pm-9:30 pm

1 stop8h 15m

$247

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

lun. 11/24

9:26 pm-2:30 pm

1 stop16h 04m

Saint Thomas Island Cyril E King

mié. 12/3

3:25 pm-8:31 pm

1 stop6h 06m

$249

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

dom. 1/25

6:05 am-1:17 pm

1 stop6h 12m

San Juan Luis Munoz Marin Intl

vie. 1/30

2:05 am-2:25 pm

2 stops13h 20m

$264

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

jue. 11/20

9:26 pm-2:30 pm

1 stop16h 04m

Saint Thomas Island Cyril E King

lun. 11/24

3:25 pm-8:31 pm

1 stop6h 06m

$269

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

lun. 1/19

10:05 am-10:22 pm

2 stops11h 17m

San Juan Luis Munoz Marin Intl

mar. 1/20

2:05 am-2:25 pm

2 stops13h 20m

$300

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mar. 12/2

7:00 am-5:20 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

mié. 12/10

1:57 pm-12:32 am

1 stop11h 35m

$301

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

dom. 2/1

6:00 am-2:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

vie. 2/6

2:05 am-2:25 pm

2 stops13h 20m

$315

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

jue. 2/19

8:09 pm-12:28 pm

1 stop15h 19m

Saint Thomas Island Cyril E King

mar. 2/24

1:33 pm-7:14 pm

1 stop6h 41m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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 $109). Flying from Chesapeake to Caribbean in February is currently the most expensive (average of $230). 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 octubre 29, 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 in the evening could potentially save you up to 20% 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 evenings 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 octubre 29, 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
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,992 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,999 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,032 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,114 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 Delta, Spirit Airlines, and United Airlines fly from Chesapeake to Caribbean in about 6h 12m. The time it takes to get you to your destination can typically vary by up to 9h 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 JetBlue. According to our data, you can fly for as low as $91. Users have also found prices from $113 and $156 on Delta and Spirit 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, May is the cheapest month in which you can book a flight from Chesapeake to Caribbean (average of $109). Flying from Chesapeake to Caribbean in February is currently the most expensive (average of $230). 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 octubre 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$309FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$108Average$429FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$208Average$593FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$537FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$242Average$616FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$255Average$614FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$266Average$566FlexibilityNo cancel feeOn-time62%

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