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$109+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Dec 25 — Jan 11
Wed 12/25
Wed 1/1
1 adult, Economy
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Cheap flight deals from Chesapeake to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Chesapeake (C6E) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 20, 2024.

Round-trip from

$207
(Cheapflightsfares)

One-way from

$109
(Mytrip)
From Chesapeake to Caribbean
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One-way flight from Chesapeake to Caribbean
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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 December 20, 2024.

This American Airlines deal was found by Cheapflights users on 12/19. 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 12/236:52 pmORF - SJU
1 stop16h 08mAmerican Airlines
Tue 12/316:05 pmSJU - ORF
1 stop7h 17mAmerican Airlines
Deal found 12/19$518
This Booking.com deal was found by Cheapflights users on 12/19. 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.
Tue 12/311:42 pmORF - SJU
1 stop12h 07mMultiple Airlines
Tue 1/711:25 pmSJU - ORF
1 stop10h 25mMultiple Airlines
Deal found 12/19$531
This Frontier deal was found by Cheapflights users on 12/19. 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 12/229:01 pmORF - SJU
1 stop11h 09mFrontier
Mon 12/306:00 amSJU - ORF
1 stop6h 02mFrontier
Deal found 12/19$593
This American Airlines deal was found by Cheapflights users on 12/18. 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 12/198:07 amORF - MBJ
1 stop6h 23mAmerican Airlines
Mon 12/233:45 pmMBJ - ORF
1 stop8h 09mAmerican Airlines
Deal found 12/18$611
This Cheapflightsfares deal was found by Cheapflights users on 12/19. 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.
Mon 12/239:45 amORF - STT
1 stop6h 05mSpirit Airlines
Thu 1/25:45 pmSTT - ORF
1 stop16h 05mSpirit Airlines
Deal found 12/19$633
This American Airlines deal was found by Cheapflights users on 12/18. 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 12/256:25 amORF - PUJ
1 stop9h 14mAmerican Airlines
Sun 12/295:45 pmPUJ - ORF
1 stop15h 47mAmerican Airlines
Deal found 12/18$651
This eDestinos deal was found by Cheapflights users on 12/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/239:45 amORF - SJU
1 stop14h 40mSpirit Airlines
Thu 1/211:25 pmSJU - ORF
1 stop10h 25mSpirit Airlines
Deal found 12/19$669
This American Airlines deal was found by Cheapflights users on 12/18. 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 12/216:59 pmORF - STT
1 stop16h 41mAmerican Airlines
Sun 12/294:10 pmSTT - ORF
1 stop9h 12mAmerican Airlines
Deal found 12/18$683
This Mytrip deal was found by Cheapflights users on 12/18. 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 12/279:26 pmORF - STT
3 stops36h 13mMultiple Airlines
Tue 1/75:45 pmSTT - ORF
1 stop16h 05mMultiple Airlines
Deal found 12/18$732
This Kiwi.com deal was found by Cheapflights users on 12/18. 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.
Wed 12/255:52 pmORF - PUJ
2 stops18h 46mMultiple Airlines
Sun 12/294:50 pmPUJ - ORF
1 stop7h 25mMultiple Airlines
Deal found 12/18$741
This Southwest deal was found by Cheapflights users on 12/18. 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.
Thu 12/196:20 amORF - SJU
2 stops9h 30mSouthwest
Sun 12/225:35 amSJU - ORF
2 stops9h 50mSouthwest
Deal found 12/18$764
This American Airlines deal was found by Cheapflights users on 12/19. 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 12/218:26 pmORF - MHH
1 stop15h 44mAmerican Airlines
Sat 12/2812:50 pmMHH - ORF
1 stop11h 32mAmerican Airlines
Deal found 12/19$796

Find flights from Chesapeake to Caribbean within your budget

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 December 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Mon 1/20

5:25 am-1:48 pm

1 stop7h 23m

Saint Thomas Island Cyril E King

Thu 1/23

2:43 pm-11:59 pm

1 stop10h 16m

$207

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 1/30

4:30 pm-11:58 pm

1 stop6h 28m

San Juan Luis Munoz Marin Intl

Tue 2/4

7:45 am-11:52 pm

1 stop17h 07m

$254

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 1/18

4:31 pm-9:21 am

1 stop15h 50m

San Juan Luis Munoz Marin Intl

Wed 1/29

4:53 pm-11:59 pm

3 stops32h 06m

$262

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 1/18

4:31 pm-9:21 am

1 stop15h 50m

San Juan Luis Munoz Marin Intl

Wed 1/29

8:40 pm-9:36 pm

2 stops25h 56m

$268

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 3/26

12:15 pm-10:13 pm

1 stop9h 58m

San Juan Luis Munoz Marin Intl

Tue 4/15

2:04 pm-11:29 pm

1 stop9h 25m

$289

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 3/8

9:05 am-7:12 pm

1 stop9h 07m

San Juan Luis Munoz Marin Intl

Wed 3/12

9:35 pm-4:58 pm

1 stop19h 23m

$298

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Mon 1/20

9:14 pm-10:46 am

3 stops36h 32m

Saint Thomas Island Cyril E King

Thu 1/23

2:43 pm-11:59 pm

1 stop10h 16m

$307

NorfolkPunta Cana

ORF - PUJ

ORFPUJ

Norfolk

Thu 3/6

5:58 pm-5:18 pm

2 stops22h 20m

Punta Cana

Sun 3/9

6:52 pm-2:37 pm

2 stops43h 45m

$340

NorfolkPunta Cana

ORF - PUJ

ORFPUJ

Norfolk

Fri 1/24

4:31 pm-3:45 pm

1 stop22h 14m

Punta Cana

Mon 1/27

4:50 pm-5:25 pm

2 stops25h 35m

$341

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sat 1/18

4:31 pm-12:10 pm

1 stop19h 39m

Montego Bay Sangster Intl

Sat 1/25

2:49 pm-8:15 pm

1 stop5h 26m

$344

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

Showing 1-10 of 39 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.

Travel insights for flights from Chesapeake to Caribbean

Get recent, data-driven insights about flights from Chesapeake to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $380). 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 December 20, 2024.

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 December 20, 2024.
Southwest
8.1
Very good
4,821 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,821 reviews
Southwest
8.1
Very good
4,821 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,600 reviews
Southwest
8.1
Very good
4,821 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Copa Airlines
7.7
Good
1,719 reviews
Southwest
8.1
Very good
4,821 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

LATAM Airlines
7.5
Good
1,876 reviews
Southwest
8.1
Very good
4,821 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,048 reviews
Southwest
8.1
Very good
4,821 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier. According to our data, you can fly for as low as $109. Users have also found prices from $117 and $128 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 - 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 March is currently the most expensive (average of $380). 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 December 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$107Average$390FlexibilityNo cancel feeOn-time65%
FrontierCheapest$158Average$285FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$613FlexibilityNo cancel feeOn-time69%
DeltaCheapest$227Average$523FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$243Average$576FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$250Average$557FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$345Average$578FlexibilityNo cancel feeOn-time63%
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