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$69+ Cheap flights from Chesapeake, VA to Fort Myers (RSW)

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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — RSW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Fort Myers SW Florida Intl are usually found in January or November, booked 86 days in advance, depart on a Saturday or Thursday and return on a Wednesday

Cheap flight deals from Chesapeake to Fort Myers

Keep the following information in mind while searching for Chesapeake to Fort Myers flight deals. Data was last updated July 31, 2025.

Round-trip from

$147
(Breeze Airways)

One-way from

$69
(Breeze Airways)

Popular in

February

Cheapest in

January

Average price

$305
From Chesapeake to Fort Myers SW Florida Intl
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One-way flight from Chesapeake to Fort Myers SW Florida Intl
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High demand for flights, 9% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Chesapeake to Fort Myers

Cheapest flights from Chesapeake to Fort Myers
Explore the most affordable flight options available from Chesapeake to Fort Myers. 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 7/29. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/94:38 pmORF - RSW
Nonstop2h 27mBreeze Airways
Sun 10/127:45 pmRSW - ORF
Nonstop2h 07mBreeze Airways
Deal found 7/29$147
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/176:10 pmORF - RSW
1 stop5h 15mAmerican Airlines
Fri 8/222:31 pmRSW - ORF
1 stop6h 39mAmerican Airlines
Deal found 7/29$237
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/125:30 amORF - RSW
1 stop4h 12mDelta
Tue 8/195:35 amRSW - ORF
1 stop7h 17mDelta
Deal found 7/31$257
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/94:38 pmORF - RSW
Nonstop2h 27mMultiple Airlines
Sun 10/125:06 pmRSW - ORF
1 stop24h 20mMultiple Airlines
Deal found 7/29$281
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.
Thu 8/73:00 pmORF - RSW
1 stop7h 40mSouthwest
Sun 8/105:30 amRSW - ORF
1 stop4h 20mSouthwest
Deal found 7/30$287
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/225:20 pmORF - RSW
2 stops15h 18mSpirit Airlines
Sun 8/247:00 amRSW - ORF
3 stops29h 44mSpirit Airlines
Deal found 7/29$326
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.
Wed 9/1010:30 amORF - RSW
1 stop5h 27mUnited Airlines
Fri 9/126:25 pmRSW - ORF
1 stop5h 25mUnited Airlines
Deal found 7/29$347

Cheapflights Fare Finder

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

Fly from

Chesapeake

Fly to

Fort Myers

Route

Depart

Return

Price

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Thu 10/9

4:38 pm-7:05 pm

Nonstop2h 27m

Fort Myers SW Florida Intl

Sun 10/12

7:45 pm-9:52 pm

Nonstop2h 07m

$147

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Sun 8/17

6:10 pm-11:25 pm

1 stop5h 15m

Fort Myers SW Florida Intl

Fri 8/22

2:31 pm-9:10 pm

1 stop6h 39m

$237

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Tue 8/12

5:30 am-9:42 am

1 stop4h 12m

Fort Myers SW Florida Intl

Tue 8/19

5:35 am-12:52 pm

1 stop7h 17m

$257

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Thu 10/9

4:38 pm-7:05 pm

Nonstop2h 27m

Fort Myers SW Florida Intl

Sun 10/12

5:06 pm-5:26 pm

1 stop24h 20m

$281

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Thu 8/7

3:00 pm-10:40 pm

1 stop7h 40m

Fort Myers SW Florida Intl

Sun 8/10

5:30 am-9:50 am

1 stop4h 20m

$287

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Fri 8/22

5:20 pm-8:38 am

2 stops15h 18m

Fort Myers SW Florida Intl

Sun 8/24

7:00 am-12:44 pm

3 stops29h 44m

$326

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Wed 9/10

10:30 am-3:57 pm

1 stop5h 27m

Fort Myers SW Florida Intl

Fri 9/12

6:25 pm-11:50 pm

1 stop5h 25m

$347

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Thu 8/21

2:06 pm-4:29 pm

Nonstop2h 23m

$69

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Mon 8/18

7:45 pm-12:36 am

1 stop4h 51m

$119

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Thu 8/21

9:50 am-6:39 pm

2 stops8h 49m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 15 results
1
2

Best time to book a flight from Chesapeake to Fort Myers

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

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

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

The best time to book flights from Chesapeake to Fort Myers is 86 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, January is the cheapest month in which you can book a flight from Chesapeake to Fort Myers (average of $205). Flying from Chesapeake to Fort Myers in June is currently the most expensive (average of $290). 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 RSW?

Find hourly flight availability from Chesapeake to Fort Myers. 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 Chesapeake to Fort Myers, 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 Chesapeake to Fort Myers?

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Fort Myers. Price data was last updated on June 15, 2025.

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

Reviews of airlines servicing Fort Myers

Get insights into the airlines that provide service to Fort Myers. 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 Fort Myers. Reviews last updated July 31, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Breeze Airways from Chesapeake to Fort Myers 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.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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 Chesapeake to Fort Myers. 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 Fort Myers from Chesapeake?

    If you book a flight to Fort Myers from Chesapeake, you will be flying to SW Florida Intl, which is the city’s only airport. Fort Myers SW Florida Intl (RSW) is located 10.0 mi from the center of Fort Myers. There are 0 flights from Chesapeake to SW Florida Intl per day from 5 different airlines.

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

    The cheapest airline one-way is Breeze Airways, with whom users have recently found tickets for as low as $69. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Chesapeake to Fort Myers for a low price.

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

    While on average a flight from Chesapeake to Fort Myers is generally $130, our data shows the cheapest flight currently is $59. When looking at the most popular route, (Norfolk - Fort Myers SW Florida Intl), you can expect to pay $138 for that flight.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chesapeake to Fort Myers (average of $205). Flying from Chesapeake to Fort Myers in June is currently the most expensive (average of $290). 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 Fort Myers?

Book flights to Fort Myers if you plan to visit one of these locations
Sanibel
North Fort Myers
Estero
Lehigh Acres

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Top 5 airlines flying from Chesapeake to Fort Myers

Discover the top 5 airlines that operate flights from Chesapeake to Fort Myers. 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$94Average$197FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$107Average$243FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$306FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$202Average$388FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$226Average$369FlexibilityNo cancel feeOn-time63%

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