HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
U.S. Virgin Islands

$230+ Cheap flights from Chesapeake, VA to the U.S. Virgin Islands

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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — STT
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chesapeake to U.S. Virgin Islands 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 U.S. Virgin Islands

Keep the following information in mind while searching for Chesapeake to U.S. Virgin Islands flight deals. Data was last updated septiembre 11, 2025.

Round-trip from

$261
(Cheapflightsfares)

One-way from

$230
(American Airlines)

Popular in

April

Cheapest in

July

Average price

$522
From Chesapeake to U.S. Virgin Islands
Search Deals
One-way flight from Chesapeake to U.S. Virgin Islands
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($105 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Chesapeake to U.S. Virgin Islands

Cheapest flights from Chesapeake to U.S. Virgin Islands
Explore the most affordable flight options available from Chesapeake to U.S. Virgin Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 11, 2025.

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.
vie. 11/78:01 amORF - STT
1 stop6h 10mSpirit Airlines
lun. 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.
mar. 11/116:00 amORF - STT
1 stop5h 28mSpirit Airlines
mar. 11/181:33 pmSTT - ORF
1 stop11h 07mSpirit Airlines
Deal found 9/10$263
This American Airlines deal was found by Cheapflights users on 9/9. 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.
mié. 11/126:00 amORF - STX
1 stop10h 52mAmerican Airlines
mar. 11/186:42 pmSTX - ORF
1 stop6h 33mAmerican Airlines
Deal found 9/9$335
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/244:57 pmORF - STT
1 stop20h 02mMultiple Airlines
mié. 10/2911:01 amSTT - ORF
1 stop11h 45mMultiple Airlines
Deal found 9/11$346
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/275:20 amORF - STT
1 stop28h 24mSpirit Airlines
jue. 10/210:49 amSTT - ORF
1 stop11h 59mSpirit Airlines
Deal found 9/10$349
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/35:20 amORF - STT
1 stop28h 24mMultiple Airlines
lun. 10/611:01 amSTT - ORF
2 stops29h 48mMultiple Airlines
Deal found 9/11$373
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/245:38 pmORF - STT
2 stops16h 18mSpirit Airlines
jue. 10/3011:01 amSTT - ORF
1 stop11h 45mSpirit Airlines
Deal found 9/11$388
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/175:38 pmORF - STT
1 stop19h 21mMultiple Airlines
mar. 10/2111:01 amSTT - ORF
2 stops35h 02mMultiple Airlines
Deal found 9/11$389
This American Airlines deal was found by Cheapflights users on 9/9. 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.
mié. 11/266:39 pmORF - STX
2 stops19h 33mAmerican Airlines
mar. 12/26:42 pmSTX - ORF
1 stop6h 33mAmerican Airlines
Deal found 9/9$409
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/245:24 amORF - STT
3 stops31h 35mSpirit Airlines
mié. 10/2911:01 amSTT - ORF
1 stop11h 45mSpirit Airlines
Deal found 9/11$430
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.
mié. 11/266:15 amORF - STX
2 stops10h 37mAmerican Airlines
mié. 12/34:07 pmSTX - ORF
2 stops18h 47mAmerican Airlines
Deal found 9/11$435
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.
jue. 9/257:04 pmORF - STX
2 stops17h 59mAmerican Airlines
lun. 9/291:53 pmSTX - ORF
2 stops19h 33mAmerican Airlines
Deal found 9/10$676

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to U.S. Virgin Islands 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 septiembre 11, 2025.
Use the filters below to find and compare flights from Chesapeake to the U.S. Virgin Islands that are best for you.

Fly from

Chesapeake

Fly to

U.S. Virgin Islands

Route

Depart

Return

Price

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

mar. 11/11

6:00 am-12:28 pm

1 stop5h 28m

Saint Thomas Island Cyril E King

mar. 11/18

1:33 pm-11:40 pm

1 stop11h 07m

$263

NorfolkChristiansted

ORF - STX

ORFSTX

Norfolk

mié. 11/12

7:01 pm-3:12 pm

2 stops19h 11m

Christiansted Henry Rohlsen

mar. 11/18

6:42 pm-12:15 am

1 stop6h 33m

$339

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

vie. 10/24

4:57 pm-12:59 pm

1 stop20h 02m

Saint Thomas Island Cyril E King

mié. 10/29

11:01 am-10:46 pm

1 stop11h 45m

$346

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

vie. 10/24

4:57 pm-12:59 pm

1 stop20h 02m

Saint Thomas Island Cyril E King

jue. 10/30

11:01 am-10:46 pm

1 stop11h 45m

$346

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

vie. 10/24

5:38 pm-9:56 am

2 stops16h 18m

Saint Thomas Island Cyril E King

jue. 10/30

11:01 am-10:46 pm

1 stop11h 45m

$388

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

vie. 11/7

8:01 am-3:11 pm

1 stop6h 10m

Saint Thomas Island Cyril E King

lun. 11/10

1:33 pm-12:07 am

3 stops35h 34m

$397

NorfolkChristiansted

ORF - STX

ORFSTX

Norfolk

mié. 11/26

6:39 pm-3:12 pm

2 stops19h 33m

Christiansted Henry Rohlsen

mar. 12/2

6:42 pm-12:15 am

1 stop6h 33m

$409

NorfolkChristiansted

ORF - STX

ORFSTX

Norfolk

mié. 11/26

6:39 pm-3:12 pm

2 stops19h 33m

Christiansted Henry Rohlsen

mié. 12/3

6:38 pm-12:28 am

1 stop6h 50m

$409

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

vie. 10/24

5:24 am-12:59 pm

3 stops31h 35m

Saint Thomas Island Cyril E King

mié. 10/29

11:01 am-10:46 pm

1 stop11h 45m

$430

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

mar. 3/10

5:30 am-11:50 am

1 stop6h 20m

Saint Thomas Island Cyril E King

mié. 3/11

1:00 pm-9:25 pm

1 stop8h 25m

$451

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 18 results
1
2

Best time to book a flight from Chesapeake to U.S. Virgin Islands

Have a flexible travel schedule? Discover the best time to fly to U.S. Virgin Islands 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 the U.S. Virgin Islands

What is the cheapest month to book a flight from Chesapeake to U.S. Virgin Islands?

Currently, September is the cheapest month in which you can book a flight from Chesapeake to U.S. Virgin Islands (average of $433). Flying from Chesapeake to U.S. Virgin Islands in June is currently the most expensive (average of $645). 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 VI?

Find hourly flight availability from Chesapeake to U.S. Virgin Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 11, 2025.

When flying from Chesapeake to U.S. Virgin Islands, 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 U.S. Virgin Islands

Get insights into the airlines that provide service to U.S. Virgin Islands. 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 U.S. Virgin Islands. Reviews last updated septiembre 11, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Chesapeake to the U.S. Virgin Islands 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.
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,023 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to U.S. Virgin Islands. 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 U.S. Virgin Islands?

    For as low as $263, Spirit Airlines can have you in U.S. Virgin Islands from Chesapeake in 5h 28m. Chesapeake and U.S. Virgin Islands are separated by a distance of 1451 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Chesapeake to U.S. Virgin Islands that include hotel bookings?

    Yes. In addition to deals on Chesapeake to U.S. Virgin Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to U.S. Virgin Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to U.S. Virgin Islands.

  • Can I find deals for business class flights from Chesapeake to U.S. Virgin Islands?

    Yes. Cheapflights offers flight deals from Chesapeake to U.S. Virgin Islands 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 U.S. Virgin Islands?

    Currently, September is the cheapest month in which you can book a flight from Chesapeake to U.S. Virgin Islands (average of $433). Flying from Chesapeake to U.S. Virgin Islands in June is currently the most expensive (average of $645). 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 U.S. Virgin Islands

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
Dulles Intl to Punta Cana flights
Raleigh to Luis Munoz Marin Intl flights
Dulles Intl to Montego Bay flights
Dulles Intl to Oranjestad flights
Dulles Intl to Saint Thomas Island flights
Reagan-National to Montego Bay flights
Reagan-National to Punta Cana flights
Dulles Intl to Nassau flights
Reagan-National to Nassau flights
Dulles Intl to Providenciales flights
Reagan-National to Saint Thomas Island flights
Reagan-National to Oranjestad flights
Dulles Intl to Santo Domingo flights
Dulles Intl to Simpson Bay flights
Dulles Intl to Castries flights
Dulles Intl to Willemstad flights
Reagan-National to Simpson Bay flights
Reagan-National to Providenciales flights
Norfolk to Luis Munoz Marin Intl flights
Reagan-National to Castries flights
Reagan-National to Santo Domingo flights
Richmond to Luis Munoz Marin Intl flights
Reagan-National to Willemstad flights
Dulles Intl to Ponce flights
Raleigh to Montego Bay flights
Richmond to Punta Cana flights
Dulles Intl to Bridgetown flights
Raleigh to Punta Cana flights
Dulles Intl to Port of Spain flights
Reagan-National to Port of Spain flights
Raleigh to Saint Thomas Island flights
Reagan-National to George Town flights
Reagan-National to Bridgetown flights
Raleigh to Oranjestad flights
Norfolk to Punta Cana flights
Reagan-National to Kingston flights
Dulles Intl to Kingston flights
Norfolk to Montego Bay flights
Dulles Intl to George Town flights
Raleigh to Nassau flights
Reagan-National to Christiansted flights
Raleigh to Santo Domingo flights
Richmond to Montego Bay flights
Richmond to Nassau flights
Raleigh to Providenciales flights
Greensboro to Punta Cana flights
Raleigh to Simpson Bay flights
Dulles Intl to Christiansted flights

Top 4 airlines flying from Chesapeake to U.S. Virgin Islands

Discover the top 4 airlines that operate flights from Chesapeake to U.S. Virgin Islands. 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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$162Average$281FlexibilityNo cancel feeOn-time65%
DeltaCheapest$283Average$467FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$284Average$563FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$332Average$568FlexibilityNo cancel feeOn-time71%

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.