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Chesapeake

$98+ Cheap flights from Fort Myers (RSW) to Chesapeake, VA

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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — RIC
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Fort Myers SW Florida Intl to Chesapeake are usually found in January or February, booked 46 days in advance, depart on a Wednesday or Tuesday and return on a Saturday

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 July 31, 2025.

Round-trip from

$98
(Breeze Airways)

Popular in

March

Cheapest in

January

Average price

$224
From Fort Myers SW Florida Intl to Chesapeake
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 31, 2025.

This Breeze Airways deal was found by Cheapflights users on 7/31. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/287:00 amRSW - ORF
Nonstop2h 09mBreeze Airways
Thu 9/45:11 pmORF - RSW
Nonstop2h 27mBreeze Airways
Deal found 7/31$98
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/284:14 pmRSW - ORF
1 stop5h 27mAmerican Airlines
Tue 9/24:00 pmORF - RSW
1 stop6h 27mAmerican Airlines
Deal found 7/31$224
This Delta deal was found by Cheapflights users on 7/30. 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 9/1511:06 amRSW - ORF
1 stop6h 33mDelta
Fri 9/195:55 pmORF - RSW
1 stop6h 40mDelta
Deal found 7/30$237
This FlightHub deal was found by Cheapflights users on 7/30. 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.
Sun 9/145:20 pmRSW - ORF
1 stop19h 50mMultiple Airlines
Thu 9/185:11 pmORF - RSW
Nonstop2h 27mMultiple Airlines
Deal found 7/30$272
This Southwest deal was found by Cheapflights users on 7/30. 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.
Tue 11/47:20 amRSW - ORF
2 stops9h 25mSouthwest
Sun 11/96:00 pmORF - RSW
1 stop3h 50mSouthwest
Deal found 7/30$290
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Tue 8/2612:28 pmRSW - ORF
1 stop9h 24mUnited Airlines
Tue 9/210:30 amORF - RSW
1 stop5h 27mUnited Airlines
Deal found 7/29$307
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Fri 9/128:01 pmRSW - ORF
2 stops20h 42mSpirit Airlines
Mon 9/155:20 amORF - RSW
2 stops15h 56mSpirit Airlines
Deal found 7/30$316

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 July 31, 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

Thu 8/28

7:00 am-9:09 am

Nonstop2h 09m

Norfolk

Thu 9/4

5:11 pm-7:38 pm

Nonstop2h 27m

$98

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Thu 8/28

4:14 pm-9:41 pm

1 stop5h 27m

Norfolk

Tue 9/2

4:00 pm-10:27 pm

1 stop6h 27m

$224

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Mon 9/15

11:06 am-5:39 pm

1 stop6h 33m

Norfolk

Fri 9/19

5:55 pm-12:35 am

1 stop6h 40m

$237

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Sun 9/14

5:20 pm-1:10 pm

1 stop19h 50m

Norfolk

Thu 9/18

5:11 pm-7:38 pm

Nonstop2h 27m

$272

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Tue 8/26

12:28 pm-9:52 pm

1 stop9h 24m

Norfolk

Tue 9/2

10:30 am-3:57 pm

1 stop5h 27m

$307

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Fri 9/12

8:01 pm-4:43 pm

2 stops20h 42m

Norfolk

Mon 9/15

5:20 am-9:16 pm

2 stops15h 56m

$316

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Mon 9/15

12:05 pm-6:40 pm

1 stop6h 35m

Norfolk

Thu 9/18

12:10 pm-9:55 pm

2 stops9h 45m

$317

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Sun 8/3

6:45 am-8:54 am

Nonstop2h 09m

$102

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Sat 10/18

9:58 am-3:10 pm

1 stop5h 12m

$119

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Fri 8/22

7:00 am-4:25 pm

3 stops33h 25m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 13 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

How far ahead should I book a flight from Fort Myers to Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from Fort Myers to Chesapeake. Price data was last updated on July 25, 2025.

The price you pay for your flight from Fort Myers to Chesapeake may vary depending on when you book. For the best chance of a lower fare, look to book 46 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 July 31, 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 July 31, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Breeze Airways 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.
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Breeze Airways
8.0
Very good
191 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • What are the cheapest airlines to fly from Fort Myers to Chesapeake one-way?

    One-way options have recently been found by users for as low as $102 on Breeze Airways. Other airlines that offer cheap prices include American Airlines from $119 and Spirit Airlines from $189 one-way.

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

    The cheapest flight price from Fort Myers to Chesapeake is $81. On average you can expect to pay $136. The most popular route, (Fort Myers SW Florida Intl - Norfolk), can usually be booked for $98.

  • 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$78Average$197FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$176Average$322FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$198Average$386FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$216Average$337FlexibilityNo cancel feeOn-time63%

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