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Freeport

$508+ Cheap flights from Chesapeake, VA to Freeport (FPO)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — FPO
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Chesapeake to Freeport

Keep the following information in mind while searching for Chesapeake to Freeport flight deals. Data was last updated September 11, 2025.

Round-trip from

$508
(Trip.com)
From Chesapeake to Freeport Grand Bahama Intl
Search Deals

Find flight deals from Chesapeake to Freeport

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

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.
Sat 10/255:24 amORF - FPO
1 stop8h 06mMultiple Airlines
Sat 11/110:45 amFPO - ORF
1 stop12h 01mMultiple Airlines
Deal found 9/10$508
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/195:24 amORF - FPO
1 stop8h 16mMultiple Airlines
Sun 10/2610:45 amFPO - ORF
1 stop12h 01mMultiple Airlines
Deal found 9/10$534
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.
Fri 11/146:00 amORF - FPO
1 stop7h 56mAmerican Airlines
Fri 11/2112:23 pmFPO - ORF
1 stop6h 26mAmerican Airlines
Deal found 9/10$565
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.
Sat 10/256:08 pmORF - FPO
2 stops19h 31mAmerican Airlines
Sat 11/12:21 pmFPO - ORF
2 stops18h 38mAmerican Airlines
Deal found 9/10$599
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 10/194:00 pmORF - FPO
2 stops21h 39mAmerican Airlines
Sun 10/262:21 pmFPO - ORF
2 stops21h 44mAmerican Airlines
Deal found 9/10$634
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.
Thu 10/234:00 pmORF - FPO
2 stops21h 39mAmerican Airlines
Mon 10/272:21 pmFPO - ORF
2 stops18h 25mAmerican Airlines
Deal found 9/10$659

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Freeport 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 Freeport that are best for you.

Fly from

Chesapeake

Fly to

Freeport

Route

Depart

Return

Price

NorfolkFreeport

ORF - FPO

ORFFPO

Norfolk

Sun 10/19

5:24 am-1:40 pm

1 stop8h 16m

Freeport Grand Bahama Intl

Sun 10/26

10:45 am-10:46 pm

1 stop12h 01m

$534

NorfolkFreeport

ORF - FPO

ORFFPO

Norfolk

Sat 10/25

5:24 am-1:30 pm

1 stop8h 06m

Freeport Grand Bahama Intl

Sat 11/1

10:45 am-11:47 am

2 stops25h 02m

$544

NorfolkFreeport

ORF - FPO

ORFFPO

Norfolk

Fri 11/14

6:00 am-1:56 pm

1 stop7h 56m

Freeport Grand Bahama Intl

Fri 11/21

12:23 pm-6:49 pm

1 stop6h 26m

$565

NorfolkFreeport

ORF - FPO

ORFFPO

Norfolk

Sat 1/10

6:41 am-11:05 am

1 stop4h 24m

Freeport Grand Bahama Intl

Sat 1/17

6:59 pm-11:51 pm

1 stop4h 52m

$595

NorfolkFreeport

ORF - FPO

ORFFPO

Norfolk

Sat 10/25

6:08 pm-1:39 pm

2 stops19h 31m

Freeport Grand Bahama Intl

Sat 11/1

2:21 pm-8:59 am

2 stops18h 38m

$599

NorfolkFreeport

ORF - FPO

ORFFPO

Norfolk

Sun 10/19

4:00 pm-1:39 pm

2 stops21h 39m

Freeport Grand Bahama Intl

Sun 10/26

2:21 pm-12:05 pm

2 stops21h 44m

$634

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Best time to book a flight from Chesapeake to Freeport

Have a flexible travel schedule? Discover the best time to fly to Freeport 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 Freeport
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Freeport

Get insights into the airlines that provide service to Freeport. 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 Freeport. Reviews last updated September 11, 2025.
Read reviews from past customers who have flown American Airlines from Chesapeake to Freeport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Overall

7.2

Entertainment

6.9

Food

6.4

Crew

8.0

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Overall

7.2

Entertainment

6.9

Food

6.4

Crew

8.0

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Freeport. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Freeport from Chesapeake?

    Located just 4.1 mi from the city center, Freeport Grand Bahama Intl is the airport most travelers will use when flying to Freeport from Chesapeake. Booking flights from Chesapeake to Grand Bahama Intl (FPO) should be relatively easy as there are 0 daily inbound flights from Chesapeake from 1 airline.

  • How long is the flight from Chesapeake to Freeport, City of Freeport?

    For as low as $565, American Airlines can have you in Freeport, City of Freeport from Chesapeake in 7h 56m. The distance between Chesapeake and Freeport, City of Freeport is about 729 mi.

  • Can I find deals for flights from Chesapeake to Freeport that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Freeport flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Freeport?

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

  • Can I find deals for business class flights from Chesapeake to Freeport?

    Yes. Cheapflights offers flight deals from Chesapeake to Freeport 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 Freeport, City of Freeport?

    Currently, September is the cheapest month in which you can book a flight from Chesapeake to Freeport, City of Freeport (average of $299). Flying from Chesapeake to Freeport, City of Freeport in December is currently the most expensive (average of $591). 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 Freeport

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Top airline flying from Chesapeake to Freeport

Discover the top airline that operate flights from Chesapeake to Freeport. 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
American AirlinesCheapest$533Average$663FlexibilityNo cancel feeOn-time71%

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