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Fort Myers

$59+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — RSW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Fort Myers SW Florida Intl are usually found in March or January, booked 86 days in advance, depart on a Friday or Saturday and return on a Wednesday

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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/45:15 pmORF - RSW
Nonstop2h 27mBreeze Airways
Sun 12/78:22 pmRSW - ORF
Nonstop2h 07mBreeze Airways
Deal found 10/28$121
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:15 pmORF - RSW
Nonstop2h 27mBreeze Airways
Sun 11/168:22 pmRSW - ORF
Nonstop2h 07mBreeze Airways
Deal found 10/28$171
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1210:05 pmORF - RSW
1 stop11h 35mBreeze Airways
Sun 11/168:22 pmRSW - ORF
Nonstop2h 07mBreeze Airways
Deal found 10/27$176
This Breeze Airways deal was found by Cheapflights users on 10/28. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:15 pmORF - RSW
Nonstop2h 27mBreeze Airways
Sun 11/98:22 pmRSW - ORF
Nonstop2h 07mBreeze Airways
Deal found 10/28$177
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/29:26 pmORF - RSW
2 stops40h 04mMultiple Airlines
Sun 12/78:22 pmRSW - ORF
Nonstop2h 07mMultiple Airlines
Deal found 10/28$181
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/39:26 pmORF - RSW
2 stops26h 32mMultiple Airlines
Sun 12/78:22 pmRSW - ORF
Nonstop2h 07mMultiple Airlines
Deal found 10/28$187
This Breeze Airways deal was found by Cheapflights users on 10/28. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/205:46 pmORF - RSW
Nonstop2h 27mBreeze Airways
Sat 12/278:53 pmRSW - ORF
Nonstop2h 06mBreeze Airways
Deal found 10/28$190
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/275:15 pmORF - RSW
Nonstop2h 27mMultiple Airlines
Tue 12/28:00 amRSW - ORF
2 stops36h 31mMultiple Airlines
Deal found 10/29$209

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 October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$98
(Breeze Airways)

One-way from

$59
(Breeze Airways)

Popular in

October

Cheapest in

March

Average price

$367
Provider with most accurate pricing for Norfolk-Fort Myers SW Florida Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Fort Myers SW Florida Intl flights.
Search Deals
From Chesapeake to Fort Myers SW Florida Intl
Search Deals
One-way flight from Chesapeake to Fort Myers SW Florida Intl
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 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 1/8

4:45 pm-7:15 pm

Nonstop2h 30m

Fort Myers SW Florida Intl

Sun 1/11

11:28 am-6:41 pm

1 stop7h 13m

$128

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Thu 1/15

7:05 am-9:35 am

Nonstop2h 30m

Fort Myers SW Florida Intl

Sun 1/18

10:15 am-12:24 pm

Nonstop2h 09m

$128

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Thu 12/4

5:15 pm-7:42 pm

Nonstop2h 27m

Fort Myers SW Florida Intl

Sun 12/7

9:25 pm-1:16 pm

1 stop15h 51m

$169

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Thu 2/5

3:07 pm-6:06 pm

1 stop26h 59m

Fort Myers SW Florida Intl

Sun 2/8

10:15 am-12:24 pm

Nonstop2h 09m

$183

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Thu 1/8

8:32 pm-12:24 pm

2 stops15h 52m

Fort Myers SW Florida Intl

Sun 1/11

10:15 am-12:24 pm

Nonstop2h 09m

$184

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Sat 12/20

5:46 pm-8:13 pm

Nonstop2h 27m

Fort Myers SW Florida Intl

Sat 12/27

8:53 pm-10:59 pm

Nonstop2h 06m

$190

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Fri 1/23

8:32 pm-10:16 pm

2 stops25h 44m

Fort Myers SW Florida Intl

Sun 1/25

7:55 pm-10:04 pm

Nonstop2h 09m

$237

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Sat 11/15

10:05 pm-9:40 am

1 stop11h 35m

Fort Myers SW Florida Intl

Mon 11/17

9:28 pm-5:38 pm

2 stops20h 10m

$246

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Sat 11/15

10:05 pm-9:40 am

1 stop11h 35m

Fort Myers SW Florida Intl

Tue 11/18

8:00 am-5:38 pm

2 stops33h 38m

$259

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Thu 11/27

5:15 pm-7:42 pm

Nonstop2h 27m

Fort Myers SW Florida Intl

Tue 12/2

8:00 am-7:07 pm

3 stops35h 07m

$268

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 21 results
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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 October 24, 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, September is the cheapest month in which you can book a flight from Chesapeake to Fort Myers (average of $67). Flying from Chesapeake to Fort Myers in November is currently the most expensive (average of $121). 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 October 30, 2025.

When flying from Chesapeake to Fort Myers, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 26% versus a flight in the evening.

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 mornings when fares are most often at their lowest. Sunday 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 October 30, 2025.
Peruse reviews from past customers who have flown with Breeze Airways, Southwest, and Delta 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.
Breeze Airways
8.1
Very good
221 reviews

Food

6.7

Boarding

8.3

Comfort

8.2

Overall

8.1

Entertainment

6.6

Crew

8.7

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
8.1
Very good
221 reviews
Breeze Airways
8.1
Very good
221 reviews

Food

6.7

Boarding

8.3

Comfort

8.2

Overall

8.1

Entertainment

6.6

Crew

8.7

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!
Southwest
8.0
Very good
4,242 reviews
Breeze Airways
8.1
Very good
221 reviews

Food

6.7

Boarding

8.3

Comfort

8.2

Overall

8.1

Entertainment

6.6

Crew

8.7

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
7.9
Good
7,993 reviews
Breeze Airways
8.1
Very good
221 reviews

Food

6.7

Boarding

8.3

Comfort

8.2

Overall

8.1

Entertainment

6.6

Crew

8.7

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
11,030 reviews
Breeze Airways
8.1
Very good
221 reviews

Food

6.7

Boarding

8.3

Comfort

8.2

Overall

8.1

Entertainment

6.6

Crew

8.7

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 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 4 different airlines.

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

    Departing from Chesapeake to Fort Myers will take you 2h 30m. The distance between Chesapeake and Fort Myers is about 786 mi. Generally, flights for this route are nonstop.

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

    While on average a flight from Chesapeake to Fort Myers is generally $146, our data shows the cheapest flight currently is $79. When looking at the most popular route, (Norfolk - Fort Myers SW Florida Intl), you can expect to pay $102 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, September is the cheapest month in which you can book a flight from Chesapeake to Fort Myers (average of $67). Flying from Chesapeake to Fort Myers in November is currently the most expensive (average of $121). 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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See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chesapeake to Fort Myers

Discover the top 4 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$89Average$198FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$176Average$313FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$216Average$367FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$218Average$395FlexibilityNo cancel feeOn-time71%

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