HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$113+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chesapeake to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 11, 2025.

Round-trip from

$225
(Delta)

One-way from

$113
(Delta)

Popular in

December

Cheapest in

September

Average price

$323
From Chesapeake to Caribbean
Search Deals
One-way flight from Chesapeake to Caribbean
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($22 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 September 2025
Search Deals

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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/11. 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 11/103:10 pmORF - SJU
1 stop7h 03mDelta
Thu 11/136:36 pmSJU - ORF
1 stop6h 39mDelta
Deal found 9/11$225
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/259:54 amORF - SJU
1 stop13h 11mAmerican Airlines
Wed 10/292:35 pmSJU - ORF
2 stops8h 25mAmerican Airlines
Deal found 9/11$230
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/229:54 amORF - SJU
1 stop14h 05mAmerican Airlines
Thu 10/235:30 amSJU - ORF
1 stop6h 35mAmerican Airlines
Deal found 9/10$240
This Frontier deal was found by Cheapflights users on 9/11. 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.
Thu 10/25:12 pmORF - SJU
1 stop9h 22mFrontier
Mon 10/69:26 pmSJU - ORF
2 stops19h 23mFrontier
Deal found 9/11$244
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Sun 10/268:30 amORF - SJU
1 stop15h 29mAmerican Airlines
Sat 11/15:30 amSJU - ORF
1 stop6h 35mAmerican Airlines
Deal found 9/10$245
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Sun 10/56:00 amORF - SJU
1 stop7h 45mUnited Airlines
Fri 10/171:05 amSJU - ORF
2 stops13h 35mUnited Airlines
Deal found 9/10$248
This United Airlines deal was found by Cheapflights users on 9/10. 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 12/96:00 amORF - SJU
2 stops14h 00mUnited Airlines
Mon 12/152:05 amSJU - ORF
2 stops13h 29mUnited Airlines
Deal found 9/10$250
This Priceline deal was found by Cheapflights users on 9/10. 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.
Thu 10/25:12 pmORF - SJU
1 stop9h 22mFrontier
Sat 10/43:39 amSJU - ORF
1 stop13h 18mFrontier
Deal found 9/10$253
This United Airlines deal was found by Cheapflights users on 9/11. 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 10/146:00 amORF - SJU
1 stop7h 45mUnited Airlines
Thu 10/161:05 amSJU - ORF
2 stops8h 32mUnited Airlines
Deal found 9/11$258
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Fri 11/78:01 amORF - STT
1 stop6h 10mSpirit Airlines
Mon 11/104:06 pmSTT - ORF
1 stop9h 01mSpirit Airlines
Deal found 9/11$261
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Sat 12/68:32 pmORF - SJU
1 stop12h 20mSpirit Airlines
Mon 12/86:00 amSJU - ORF
1 stop9h 12mSpirit Airlines
Deal found 9/10$262
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Tue 11/116:00 amORF - STT
1 stop5h 28mSpirit Airlines
Tue 11/181:33 pmSTT - ORF
1 stop11h 07mSpirit Airlines
Deal found 9/10$263

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 September 11, 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

Fri 10/3

1:10 pm-12:45 am

1 stop11h 35m

San Juan Luis Munoz Marin Intl

Sun 10/5

5:45 am-4:50 pm

1 stop11h 05m

$225

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 10/18

8:30 am-11:05 pm

1 stop14h 35m

San Juan Luis Munoz Marin Intl

Fri 10/24

5:00 pm-11:16 pm

1 stop6h 16m

$225

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 11/10

6:35 am-3:40 pm

1 stop8h 05m

San Juan Luis Munoz Marin Intl

Tue 11/11

2:05 am-2:34 pm

2 stops13h 29m

$225

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Tue 11/11

6:00 am-12:28 pm

1 stop5h 28m

Saint Thomas Island Cyril E King

Tue 11/18

1:33 pm-11:40 pm

1 stop11h 07m

$263

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 10/2

6:45 pm-12:45 am

1 stop6h 00m

San Juan Luis Munoz Marin Intl

Mon 10/6

5:30 pm-11:25 pm

1 stop5h 55m

$285

NorfolkOranjestad

ORF - AUA

ORFAUA

Norfolk

Wed 11/19

6:00 am-4:50 pm

1 stop9h 50m

Oranjestad Reina Beatrix

Mon 11/24

5:55 pm-12:15 am

1 stop7h 20m

$286

NorfolkOranjestad

ORF - AUA

ORFAUA

Norfolk

Fri 11/14

7:29 pm-2:42 pm

2 stops18h 13m

Oranjestad Reina Beatrix

Fri 11/21

5:45 pm-9:36 am

2 stops16h 51m

$291

NorfolkOranjestad

ORF - AUA

ORFAUA

Norfolk

Tue 10/28

6:14 am-12:30 pm

1 stop6h 16m

Oranjestad Reina Beatrix

Sat 11/1

2:45 pm-10:20 am

2 stops19h 35m

$291

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 1/8

5:30 am-1:00 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

Fri 1/16

7:30 am-4:59 pm

1 stop10h 29m

$295

NorfolkOranjestad

ORF - AUA

ORFAUA

Norfolk

Fri 1/16

7:40 pm-12:30 pm

1 stop15h 50m

Oranjestad Reina Beatrix

Fri 1/30

3:10 pm-10:55 pm

1 stop8h 45m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 60 results
1
2
3
...
6

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 September 11, 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 September 11, 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
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

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
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

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
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

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 American Airlines, Spirit Airlines, and Southwest fly from Chesapeake to Caribbean in about 5h 28m. The time it takes to get you to your destination can typically vary by up to 9h 07m. Airlines will cover a distance of 1451 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 Delta. According to our data, you can fly for as low as $113. Users have also found prices from $113 and $143 on American Airlines 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 - Punta Cana 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chesapeake to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Dallas/Fort Worth flights
Dulles Intl to Las Vegas flights
Dulles Intl to Cancún flights
Dulles Intl to Atlanta flights
Reagan-National to O'Hare Intl flights
Reagan-National to Los Angeles flights
Reagan-National to Dallas/Fort Worth flights
Dulles Intl to O'Hare Intl flights
Dulles Intl to Orlando flights
Reagan-National to Las Vegas flights
Dulles Intl to Los Angeles flights
Reagan-National to Miami flights
Dulles Intl to Seattle flights
Reagan-National to Boston flights
Raleigh to LaGuardia flights
Raleigh to John F Kennedy Intl flights
Dulles Intl to Miami flights
Reagan-National to Hobby flights
Reagan-National to Seattle flights
Reagan-National to San Francisco flights
Dulles Intl to Boston flights
Reagan-National to Orlando flights
Dulles Intl to Heathrow flights
Reagan-National to Cancún flights
Dulles Intl to San Francisco flights
Dulles Intl to Hobby flights
Reagan-National to Atlanta flights
Raleigh to Las Vegas flights
Dulles Intl to Detroit flights
Dulles Intl to New Orleans flights
Dulles Intl to Tampa flights
Dulles Intl to Luis Munoz Marin Intl flights
Dulles Intl to Midway flights
Dulles Intl to Denver flights
Dulles Intl to Mexico City flights
Raleigh to Boston flights
Raleigh to Newark flights
Reagan-National to Fort Lauderdale flights
Dulles Intl to Charles de Gaulle flights
Reagan-National to Luis Munoz Marin Intl flights
Dulles Intl to Sky Harbor Intl flights
Reagan-National to Detroit flights
Dulles Intl to Haneda flights
Reagan-National to George Bush Intcntl flights
Dulles Intl to Fort Lauderdale flights
Reagan-National to Denver flights
Dulles Intl to George Bush Intcntl flights
Reagan-National to Minneapolis flights
Dulles Intl to San Salvador flights
Dulles Intl to Austin flights

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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$284FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$108Average$428FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$204Average$563FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$593FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$524FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$254Average$615FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$257Average$643FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.