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$117+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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 November 21, 2024.

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 November 21, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/129:19 pmORF - STT
1 stop15h 04mSpirit Airlines
Mon 12/1611:56 amSTT - ORF
1 stop12h 09mSpirit Airlines
Deal found 11/21$229
This FlightHub deal was found by Cheapflights users on 11/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/115:45 amORF - SJU
1 stop13h 37mSpirit Airlines
Wed 12/112:45 amSJU - ORF
1 stop18h 39mSpirit Airlines
Deal found 11/21$279
This Delta deal was found by Cheapflights users on 11/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2412:29 pmORF - SJU
1 stop9h 50mDelta
Mon 12/306:30 amSJU - ORF
1 stop11h 28mDelta
Deal found 11/21$284
This Frontier deal was found by Cheapflights users on 11/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/169:54 amORF - SJU
1 stop13h 05mFrontier
Sun 12/223:54 amSJU - ORF
1 stop8h 08mFrontier
Deal found 11/21$298
This Mytrip deal was found by Cheapflights users on 11/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/115:45 amORF - SJU
1 stop13h 37mMultiple Airlines
Thu 12/128:31 pmSJU - ORF
2 stops27h 23mMultiple Airlines
Deal found 11/21$305
This Mytrip deal was found by Cheapflights users on 11/20. 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 12/49:36 pmORF - STT
3 stops38h 47mMultiple Airlines
Wed 12/1111:56 amSTT - ORF
1 stop9h 17mMultiple Airlines
Deal found 11/20$338
This United Airlines deal was found by Cheapflights users on 11/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/112:45 pmORF - SJU
1 stop8h 51mUnited Airlines
Tue 2/112:05 amSJU - ORF
1 stop9h 48mUnited Airlines
Deal found 11/21$379
This FlightHub deal was found by Cheapflights users on 11/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/59:19 pmORF - MBJ
2 stops40h 14mSpirit Airlines
Sun 12/82:38 pmMBJ - ORF
2 stops29h 46mSpirit Airlines
Deal found 11/21$383
This Mytrip deal was found by Cheapflights users on 11/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/59:19 pmORF - MBJ
2 stops16h 14mMultiple Airlines
Tue 12/102:38 pmMBJ - ORF
2 stops17h 55mMultiple Airlines
Deal found 11/21$426
This FlightHub deal was found by Cheapflights users on 11/20. 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.
Tue 12/35:20 amORF - AUA
1 stop9h 20mSpirit Airlines
Sun 12/84:40 pmAUA - ORF
1 stop7h 25mSpirit Airlines
Deal found 11/20$435
This Delta deal was found by Cheapflights users on 11/20. 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.
Thu 12/195:29 amORF - STT
1 stop9h 41mDelta
Tue 12/243:01 pmSTT - ORF
1 stop8h 49mDelta
Deal found 11/20$438
This American Airlines deal was found by Cheapflights users on 11/21. 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.
Tue 12/37:23 pmORF - SDQ
1 stop15h 47mAmerican Airlines
Fri 12/63:05 pmSDQ - ORF
1 stop9h 39mAmerican Airlines
Deal found 11/21$444

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Thu 12/12

9:19 pm-1:23 pm

1 stop15h 04m

Saint Thomas Island Cyril E King

Mon 12/16

11:56 am-11:05 pm

1 stop12h 09m

$229

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 2/20

7:49 pm-8:40 pm

1 stop23h 51m

San Juan Luis Munoz Marin Intl

Sun 2/23

2:45 am-6:50 pm

1 stop17h 05m

$268

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Fri 12/6

6:48 am-5:15 pm

1 stop9h 27m

San Juan Luis Munoz Marin Intl

Wed 12/11

1:49 pm-9:57 pm

1 stop9h 08m

$269

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 1/15

5:25 am-2:10 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Wed 1/22

8:43 pm-9:36 pm

2 stops25h 53m

$287

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 2/13

6:34 pm-9:35 am

1 stop14h 01m

San Juan Luis Munoz Marin Intl

Mon 2/17

10:37 pm-5:34 pm

1 stop19h 57m

$311

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 12/3

2:48 pm-12:36 am

1 stop8h 48m

San Juan Luis Munoz Marin Intl

Fri 12/13

2:05 am-2:27 pm

2 stops13h 22m

$314

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Fri 1/3

9:45 am-1:45 pm

1 stop28h 00m

Montego Bay Sangster Intl

Thu 1/9

2:42 pm-11:59 pm

2 stops9h 17m

$315

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 2/25

10:12 am-11:55 pm

1 stop12h 43m

San Juan Luis Munoz Marin Intl

Tue 3/4

2:25 pm-10:51 pm

2 stops9h 26m

$319

NorfolkChristiansted

ORF - STX

ORFSTX

Norfolk

Fri 2/7

4:21 pm-4:00 pm

1 stop22h 39m

Christiansted Henry Rohlsen

Mon 2/10

5:05 pm-5:27 pm

2 stops25h 22m

$326

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Wed 12/4

9:36 pm-1:23 pm

3 stops38h 47m

Saint Thomas Island Cyril E King

Wed 12/11

11:56 am-8:13 pm

1 stop9h 17m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 54 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 $335). 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 November 21, 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 November 21, 2024.
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

KLM
7.8
Good
1,349 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Copa Airlines
7.8
Good
1,779 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

LATAM Airlines
7.5
Good
1,932 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $117. Users have also found prices from $122 and $134 on American Airlines and Frontier, 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 $335). 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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$107Average$394FlexibilityNo cancel feeOn-time65%
FrontierCheapest$158Average$278FlexibilityNo cancel feeOn-time62%
DeltaCheapest$227Average$514FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$240Average$609FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$247Average$574FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$250Average$570FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$329Average$512FlexibilityNo cancel feeOn-time63%
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