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Chesapeake

$59+ Cheap flights from Fort Myers (RSW) to Chesapeake, VA

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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — RIC
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Fort Myers to Chesapeake

Keep the following information in mind while searching for Fort Myers to Chesapeake flight deals. Data was last updated September 16, 2025.

Round-trip from

$131
(Kiwi.com)

One-way from

$59
(Breeze Airways)

Popular in

December

Cheapest in

January

Average price

$297
From Fort Myers SW Florida Intl to Chesapeake
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One-way flight from Fort Myers SW Florida Intl to Chesapeake
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Highest demand for flights based on searches. 6% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Fort Myers to Chesapeake

Cheapest flights from Fort Myers to Chesapeake
Explore the most affordable flight options available from Fort Myers to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sun 9/288:18 pmRSW - ORF
Nonstop2h 07mBreeze Airways
Sun 10/54:38 pmORF - RSW
Nonstop2h 27mBreeze Airways
Deal found 9/15$131
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sun 9/288:18 pmRSW - ORF
Nonstop2h 07mMultiple Airlines
Sun 10/512:14 pmORF - RSW
2 stops8h 31mMultiple Airlines
Deal found 9/15$201
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/307:45 pmRSW - ORF
Nonstop2h 07mBreeze Airways
Mon 11/34:57 pmORF - RSW
2 stops24h 49mBreeze Airways
Deal found 9/15$234
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/175:40 pmRSW - ORF
1 stop13h 45mBreeze Airways
Sun 10/194:38 pmORF - RSW
Nonstop2h 27mBreeze Airways
Deal found 9/15$238
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/307:45 pmRSW - ORF
Nonstop2h 07mMultiple Airlines
Mon 11/35:24 amORF - RSW
3 stops15h 53mMultiple Airlines
Deal found 9/15$254
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/1710:36 pmRSW - ORF
3 stops24h 10mMultiple Airlines
Sun 10/194:38 pmORF - RSW
Nonstop2h 27mMultiple Airlines
Deal found 9/15$279
This Southwest deal was found by Cheapflights users on 9/16. 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.
Sat 10/187:30 amRSW - ORF
1 stop6h 20mSouthwest
Tue 10/212:55 pmORF - RSW
2 stops6h 45mSouthwest
Deal found 9/16$280
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/188:26 amRSW - ORF
2 stops8h 41mAmerican Airlines
Tue 10/219:54 amORF - RSW
2 stops7h 55mAmerican Airlines
Deal found 9/16$286
This Delta deal was found by Cheapflights users on 9/14. 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.
Mon 10/206:41 pmRSW - ORF
1 stop5h 39mDelta
Mon 10/277:45 pmORF - RSW
1 stop4h 54mDelta
Deal found 9/14$313

Cheapflights Fare Finder

 
Customize your flight search to find flights from Fort Myers to Chesapeake 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 16, 2025.
Use the filters below to find and compare flights from Fort Myers to Chesapeake that are best for you.

Fly from

Fort Myers

Fly to

Chesapeake

Route

Depart

Return

Price

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Sun 9/28

8:18 pm-10:25 pm

Nonstop2h 07m

Norfolk

Sun 10/5

9:36 pm-4:27 pm

1 stop18h 51m

$226

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Thu 10/30

7:45 pm-9:52 pm

Nonstop2h 07m

Norfolk

Mon 11/3

4:57 pm-5:46 pm

2 stops24h 49m

$234

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Thu 11/27

8:22 pm-10:29 pm

Nonstop2h 07m

Norfolk

Sun 11/30

5:15 pm-7:42 pm

Nonstop2h 27m

$251

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Sun 9/28

8:18 pm-10:25 pm

Nonstop2h 07m

Norfolk

Sun 10/5

5:47 pm-3:14 pm

3 stops21h 27m

$275

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Sat 10/18

9:58 am-3:10 pm

1 stop5h 12m

Norfolk

Tue 10/21

8:30 am-1:48 pm

1 stop5h 18m

$275

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Mon 10/20

6:41 pm-12:20 am

1 stop5h 39m

Norfolk

Mon 10/27

7:45 pm-12:39 am

1 stop4h 54m

$313

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Sat 12/6

10:26 am-2:25 pm

1 stop3h 59m

Norfolk

Sat 12/13

5:08 am-9:34 am

1 stop4h 26m

$313

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Wed 10/22

5:38 am-11:17 am

1 stop5h 39m

Norfolk

Fri 10/24

7:45 pm-12:39 am

1 stop4h 54m

$321

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Thu 11/27

7:05 am-10:40 am

1 stop3h 35m

Norfolk

Sun 11/30

5:20 am-10:20 am

1 stop5h 00m

$332

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Thu 10/30

7:10 am-3:10 pm

2 stops8h 00m

Norfolk

Mon 11/3

12:15 pm-8:10 pm

2 stops7h 55m

$332

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 18 results
1
2

Best time to book a flight from Fort Myers to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Fort Myers 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 Fort Myers to Chesapeake

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

Currently, January is the cheapest month in which you can book a flight from Fort Myers to Chesapeake (average of $281). Flying from Fort Myers to Chesapeake in March is currently the most expensive (average of $351). 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 RSW to C6E?

Find hourly flight availability from Fort Myers to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Fort Myers to Chesapeake, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Fort Myers to Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from Fort Myers to Chesapeake. Price data was last updated on May 11, 2025.

Travelers seeking maximum savings on their Fort Myers to Chesapeake flight should consider departing on Friday evenings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chesapeake

Get insights into the airlines that provide service to Chesapeake. 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 Chesapeake. Reviews last updated September 16, 2025.
Read reviews from past customers who have flown Breeze Airways, Delta, and American Airlines from Fort Myers to Chesapeake. 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.
Breeze Airways
8.0
Very good
205 reviews

Overall

8.0

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

6.7

Entertainment

6.5

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.0
Very good
205 reviews
Breeze Airways
8.0
Very good
205 reviews

Overall

8.0

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

6.7

Entertainment

6.5

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Delta
8.0
Very good
7,957 reviews
Breeze Airways
8.0
Very good
205 reviews

Overall

8.0

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

6.7

Entertainment

6.5

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.0
Very good
205 reviews

Overall

8.0

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

6.7

Entertainment

6.5

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

Related info for your journey

Find useful and relevant information for your journey from Fort Myers to Chesapeake. 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 from for flights from Fort Myers to Chesapeake?

    For a flight from Fort Myers to Chesapeake, you will be flying from SW Florida Intl. Fort Myers SW Florida Intl (RSW) is just 10.0 mi from the center of the city. SW Florida Intl is the only Fort Myers airport and it handles 0 outbound flights to Chesapeake per day. 4 airlines have flights to Chesapeake from Fort Myers SW Florida Intl on a regular basis.

  • How popular is this Fort Myers to Chesapeake flight route?

    Flights from Fort Myers SW Florida Intl to Chesapeake have been viewed 1 times in the past calendar month.

  • How long is the flight from Fort Myers to Chesapeake?

    For as low as $226, Breeze Airways can have you in Chesapeake from Fort Myers in 2h 07m. The distance from Fort Myers to Chesapeake is about 786 mi. All flights are typically nonstop.

  • What are the cheapest flights from Fort Myers to Chesapeake?

    The cheapest flight price from Fort Myers to Chesapeake is $59. On average you can expect to pay $206. The most popular route, (Fort Myers SW Florida Intl - Norfolk), can usually be booked for $131.

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

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

  • How can I find direct flights from Fort Myers to Chesapeake?

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

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

    Yes. Cheapflights offers flight deals from Fort Myers to Chesapeake 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 Fort Myers to Chesapeake?

    Currently, January is the cheapest month in which you can book a flight from Fort Myers to Chesapeake (average of $281). Flying from Fort Myers to Chesapeake in March is currently the most expensive (average of $351). 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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Top 4 airlines flying from Fort Myers to Chesapeake

Discover the top 4 airlines that operate flights from Fort Myers to Chesapeake. 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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$78Average$189FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$169Average$303FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$218Average$392FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$247Average$416FlexibilityNo cancel feeOn-time63%

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