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$422+ Cheap flights from Chesapeake, VA to Naples (NAP)

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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — NAP
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Chesapeake to Naples

Cheapest flights from Chesapeake to Naples
Explore the most affordable flight options available from Chesapeake to Naples. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This KLM deal was found by Cheapflights users on 1/27. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/95:59 pm
ORF
-
NAP
2 stops16h 51m
Multiple Airlines
Wed 3/2510:25 am
NAP
-
ORF
2 stops18h 59m
Multiple Airlines
Deal found 1/27$492
This Cheapflightsfares deal was found by Cheapflights users on 1/26. 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.
Wed 2/2512:26 pm
ORF
-
NAP
2 stops23h 49m
Lufthansa
Wed 3/41:15 pm
NAP
-
ORF
2 stops16h 19m
Lufthansa
Deal found 1/26$494
This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:31 pm
ORF
-
NAP
2 stops16h 04m
Multiple Airlines
Wed 3/116:20 am
NAP
-
ORF
2 stops20h 48m
Multiple Airlines
Deal found 1/28$495
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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.
Wed 8/511:29 am
ORF
-
NAP
2 stops18h 46m
Lufthansa
Wed 8/191:05 pm
NAP
-
ORF
2 stops16h 31m
Lufthansa
Deal found 1/28$535
This oojo deal was found by Cheapflights users on 1/28. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:00 pm
ORF
-
NAP
2 stops23h 00m
British Airways
Tue 8/183:30 pm
NAP
-
ORF
2 stops37h 35m
British Airways
Deal found 1/28$542
This Air Canada deal was found by Cheapflights users on 1/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/511:29 am
ORF
-
NAP
2 stops16h 11m
Multiple Airlines
Wed 8/196:25 am
NAP
-
ORF
3 stops18h 05m
Multiple Airlines
Deal found 1/28$614
This United Airlines deal was found by Cheapflights users on 1/28. 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 8/56:00 am
ORF
-
NAP
2 stops21h 40m
United Airlines
Tue 8/181:15 pm
NAP
-
ORF
3 stops40h 21m
United Airlines
Deal found 1/28$631
This Delta deal was found by Cheapflights users on 1/28. 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.
Wed 8/57:00 am
ORF
-
NAP
2 stops21h 35m
Delta
Wed 8/199:15 am
NAP
-
ORF
1 stop15h 43m
Delta
Deal found 1/28$640
This Air Canada deal was found by Cheapflights users on 1/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:00 am
ORF
-
NAP
3 stops21h 40m
Air Canada
Wed 8/196:25 am
NAP
-
ORF
3 stops18h 05m
Air Canada
Deal found 1/28$685
This KLM deal was found by Cheapflights users on 1/28. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:29 pm
ORF
-
NAP
1 stop32h 41m
KLM
Wed 8/199:15 am
NAP
-
ORF
1 stop15h 43m
KLM
Deal found 1/28$686
This Gurufare deal was found by Cheapflights users on 1/28. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:45 pm
ORF
-
NAP
2 stops40h 40m
Lufthansa
Sat 3/216:15 pm
NAP
-
ORF
2 stops34h 31m
Lufthansa
Deal found 1/28$690

Find flight deals from Chesapeake to Naples

Keep the following information in mind while searching for Chesapeake to Naples flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$492
(KLM)

One-way from

$422
(oojo)

Popular in

May

Cheapest in

January

Average price

$546
Provider with most accurate pricing for Norfolk-Naples flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Naples flights.
Search Deals
From Chesapeake to Naples
Search Deals
One-way flight from Chesapeake to Naples
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($262 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($49 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Naples 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 January 29, 2026.
Use the filters below to find and compare flights from Chesapeake to Naples that are best for you.

Fly from

Chesapeake

Fly to

Naples

Route

Depart

Return

Price

NorfolkNaples

ORF - NAP

ORFNAP

Norfolk

Mon 3/9

5:59 pm-3:50 pm

2 stops16h 51m

Naples

Wed 3/25

10:25 am-12:24 am

2 stops18h 59m

$492

NorfolkNaples

ORF - NAP

ORFNAP

Norfolk

Wed 2/25

9:03 am-11:45 am

2 stops20h 42m

Naples

Sun 3/1

12:35 pm-5:01 pm

2 stops34h 26m

$705

NorfolkNaples

ORF - NAP

ORFNAP

Norfolk

Mon 2/9

6:10 am-2:10 pm

2 stops26h 00m

Naples

Fri 2/27

6:20 am-10:08 pm

2 stops21h 48m

$765

NorfolkNaples

ORF - NAP

ORFNAP

Norfolk

Sun 2/22

12:26 pm-10:35 am

2 stops16h 09m

Naples

Fri 3/13

6:35 am-11:46 pm

2 stops22h 11m

$768

NorfolkNaples

ORF - NAP

ORFNAP

Norfolk

Sun 2/15

6:20 am-10:35 am

2 stops22h 15m

Naples

Fri 2/27

6:35 am-9:11 pm

2 stops20h 36m

$768

NorfolkNaples

ORF - NAP

ORFNAP

Norfolk

Tue 2/10

1:01 pm-9:15 pm

2 stops26h 14m

Naples

Tue 2/17

12:20 pm-11:00 pm

2 stops16h 40m

$788

NorfolkNaples

ORF - NAP

ORFNAP

Norfolk

Thu 2/19

4:55 pm-6:15 pm

2 stops43h 20m

Naples

Mon 2/23

2:15 pm-9:11 pm

2 stops36h 56m

$838

NorfolkNaples

ORF - NAP

ORFNAP

Norfolk

Sat 2/21

7:05 pm-1:05 pm

2 stops36h 00m

Naples

Sat 3/7

6:15 am-10:08 pm

2 stops21h 53m

$844

NorfolkNaples

ORF - NAP

ORFNAP

Norfolk

Sun 7/26

4:20 pm-2:00 pm

2 stops15h 40m

Naples

Thu 8/6

12:00 pm-11:05 pm

1 stop17h 05m

$850

NorfolkNaples

ORF - NAP

ORFNAP

Norfolk

Wed 7/1

12:57 pm-1:00 pm

1 stop18h 03m

$422

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 12 results
1
2

Best time to book a flight from Chesapeake to Naples

Have a flexible travel schedule? Discover the best time to fly to Naples 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 Naples

What is the cheapest month to book a flight from Chesapeake to Naples?

Currently, January is the cheapest month in which you can book a flight from Chesapeake to Naples (average of $490). Flying from Chesapeake to Naples in February is currently the most expensive (average of $1,384). 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.

Reviews of airlines servicing Naples

Get insights into the airlines that provide service to Naples. 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 Naples. Reviews last updated January 29, 2026.
Read through reviews of airlines operating flights from Chesapeake to Naples, such as KLM, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
KLM
7.7
Good
1,443 reviews

Comfort

7.6

Entertainment

7.1

Food

7.3

Boarding

7.8

Crew

8.4

Overall

7.7

Reviews

1 / 20
10.0
Excellent

Snapyou,Jan 2026

TPA - LHR

Flight operated by Virgin Atlantic - usual high standard service by Virgin.
KLM
7.7
Good
1,443 reviews
KLM
7.7
Good
1,443 reviews

Comfort

7.6

Entertainment

7.1

Food

7.3

Boarding

7.8

Crew

8.4

Overall

7.7

Reviews

1 / 20
10.0
Excellent

Snapyou,Jan 2026

TPA - LHR

Flight operated by Virgin Atlantic - usual high standard service by Virgin.
United Airlines
7.4
Good
9,215 reviews
KLM
7.7
Good
1,443 reviews

Comfort

7.6

Entertainment

7.1

Food

7.3

Boarding

7.8

Crew

8.4

Overall

7.7

Reviews

1 / 20
10.0
Excellent

Snapyou,Jan 2026

TPA - LHR

Flight operated by Virgin Atlantic - usual high standard service by Virgin.
American Airlines
7.2
Good
11,206 reviews
KLM
7.7
Good
1,443 reviews

Comfort

7.6

Entertainment

7.1

Food

7.3

Boarding

7.8

Crew

8.4

Overall

7.7

Reviews

1 / 20
10.0
Excellent

Snapyou,Jan 2026

TPA - LHR

Flight operated by Virgin Atlantic - usual high standard service by Virgin.
Lufthansa
6.8
Okay
7,756 reviews
KLM
7.7
Good
1,443 reviews

Comfort

7.6

Entertainment

7.1

Food

7.3

Boarding

7.8

Crew

8.4

Overall

7.7

Reviews

1 / 20
10.0
Excellent

Snapyou,Jan 2026

TPA - LHR

Flight operated by Virgin Atlantic - usual high standard service by Virgin.
British Airways
6.7
Okay
7,705 reviews
KLM
7.7
Good
1,443 reviews

Comfort

7.6

Entertainment

7.1

Food

7.3

Boarding

7.8

Crew

8.4

Overall

7.7

Reviews

1 / 20
10.0
Excellent

Snapyou,Jan 2026

TPA - LHR

Flight operated by Virgin Atlantic - usual high standard service by Virgin.

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Naples. 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 Naples from Chesapeake?

    Located just 2.9 mi from the city center, Naples is the airport most travelers will use when flying to Naples from Chesapeake. Booking flights from Chesapeake to Naples (NAP) should be relatively easy as there are 0 daily inbound flights from Chesapeake from 5 different airlines.

  • How long is the flight from Chesapeake to Naples?

    For as low as $705, British Airways can have you in Naples from Chesapeake in 20h 42m. Airlines will cover a distance of 4639 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chesapeake to Naples 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 Naples?

    Currently, January is the cheapest month in which you can book a flight from Chesapeake to Naples (average of $490). Flying from Chesapeake to Naples in February is currently the most expensive (average of $1,384). 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

Traveling to a place near Naples?

Book flights to Naples if you plan to visit one of these locations
Praiano
Ravello
Conca Dei Marini
Maiori
Sant'Agnello
Vico Equense

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Top 5 airlines flying from Chesapeake to Naples

Discover the top 5 airlines that operate flights from Chesapeake to Naples. 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
LufthansaCheapest$537Average$677FlexibilityNo cancel feeOn-time76%
KLMCheapest$659Average$820FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$757Average$1,198FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$763Average$1,033FlexibilityNo cancel feeOn-time69%
British AirwaysCheapest$893Average$1,193FlexibilityNo cancel feeOn-time70%

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