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Fort Myers

$96+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — RSW
mars 5 — mars 121
jeu. 3/5
jeu. 3/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Fort Myers SW Florida Intl are usually found in March or September, booked 84 days in advance, depart on a Friday or Saturday and return on a Wednesday

Cheap 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 février 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
jeu. 5/710:38 am
ORF
-
RSW
Nonstop2h 25m
Breeze Airways
jeu. 5/147:45 am
RSW
-
ORF
Nonstop2h 13m
Breeze Airways
Deal found 2/2$136
This Breeze Airways deal was found by Cheapflights users on 2/3. 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.
dim. 3/227:05 am
ORF
-
RSW
Nonstop2h 30m
Breeze Airways
jeu. 3/2610:15 am
RSW
-
ORF
Nonstop2h 09m
Breeze Airways
Deal found 2/3$158
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
jeu. 2/1911:46 am
ORF
-
RSW
1 stop24h 15m
Multiple Airlines
jeu. 3/58:00 am
RSW
-
ORF
1 stop9h 05m
Multiple Airlines
Deal found 2/1$174
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
dim. 2/87:05 am
ORF
-
RSW
Nonstop2h 30m
Multiple Airlines
dim. 2/87:36 pm
RSW
-
ORF
1 stop15h 12m
Multiple Airlines
Deal found 2/1$183
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
dim. 2/2211:32 am
ORF
-
RSW
1 stop24h 29m
Multiple Airlines
jeu. 2/268:00 am
RSW
-
ORF
1 stop9h 05m
Multiple Airlines
Deal found 2/1$185
This Priceline deal was found by Cheapflights users on 2/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/2312:33 pm
ORF
-
RSW
1 stop5h 57m
Multiple Airlines
jeu. 3/2610:15 am
RSW
-
ORF
Nonstop2h 09m
Multiple Airlines
Deal found 2/1$190
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
lun. 3/1612:33 pm
ORF
-
RSW
1 stop5h 57m
Multiple Airlines
lun. 3/237:35 pm
RSW
-
ORF
2 stops24h 11m
Multiple Airlines
Deal found 2/3$195

Find 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 février 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$136
(Kiwi.com)

One-way from

$96
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$305
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. 11% potential increase in price ($41 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 February 2026
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 février 3, 2026.
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

lun. 3/16

12:33 pm-6:30 pm

1 stop5h 57m

Fort Myers SW Florida Intl

mer. 3/18

7:10 pm-10:15 am

1 stop15h 05m

$225

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

dim. 3/22

7:05 am-9:35 am

Nonstop2h 30m

Fort Myers SW Florida Intl

mer. 3/25

7:27 pm-7:46 pm

2 stops24h 19m

$227

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

dim. 3/22

7:05 am-9:35 am

Nonstop2h 30m

Fort Myers SW Florida Intl

dim. 3/29

8:00 am-5:05 pm

1 stop9h 05m

$237

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

lun. 3/16

12:33 pm-6:30 pm

1 stop5h 57m

Fort Myers SW Florida Intl

ven. 3/20

7:35 pm-7:46 pm

2 stops24h 11m

$250

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

mar. 3/17

8:41 pm-6:15 pm

2 stops21h 34m

Fort Myers SW Florida Intl

sam. 3/21

7:30 pm-2:55 pm

1 stop19h 25m

$266

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

mer. 3/18

6:45 am-6:15 pm

2 stops11h 30m

Fort Myers SW Florida Intl

jeu. 3/19

8:00 am-5:05 pm

1 stop9h 05m

$270

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

ven. 3/20

11:37 am-6:30 pm

1 stop6h 53m

Fort Myers SW Florida Intl

lun. 3/23

9:54 pm-7:46 pm

2 stops21h 52m

$304

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

sam. 2/28

3:01 pm-8:42 pm

1 stop5h 41m

Fort Myers SW Florida Intl

lun. 3/2

3:33 pm-10:53 pm

1 stop7h 20m

$323

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

dim. 3/15

11:25 am-3:05 pm

2 stops27h 40m

Fort Myers SW Florida Intl

sam. 3/21

7:30 pm-2:55 pm

1 stop19h 25m

$323

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

jeu. 4/2

11:31 am-6:41 pm

1 stop7h 10m

Fort Myers SW Florida Intl

dim. 4/5

7:41 pm-7:46 pm

2 stops24h 05m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 19 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 January 30, 2026.

The best time to book flights from Chesapeake to Fort Myers is 82 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 July is currently the most expensive (average of $120). 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 février 3, 2026.

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 evening, which can drop the price by up to 42% versus a flight in the afternoon.

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 février 3, 2026.
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
8.2
Very good
263 reviews

Overall

8.2

Crew

8.7

Comfort

8.2

Food

6.7

Boarding

8.3

Entertainment

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.2
Very good
263 reviews
Breeze Airways
8.2
Very good
263 reviews

Overall

8.2

Crew

8.7

Comfort

8.2

Food

6.7

Boarding

8.3

Entertainment

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Southwest
8.0
Very good
4,272 reviews
Breeze Airways
8.2
Very good
263 reviews

Overall

8.2

Crew

8.7

Comfort

8.2

Food

6.7

Boarding

8.3

Entertainment

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Delta
7.9
Good
8,138 reviews
Breeze Airways
8.2
Very good
263 reviews

Overall

8.2

Crew

8.7

Comfort

8.2

Food

6.7

Boarding

8.3

Entertainment

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.2
Good
11,216 reviews
Breeze Airways
8.2
Very good
263 reviews

Overall

8.2

Crew

8.7

Comfort

8.2

Food

6.7

Boarding

8.3

Entertainment

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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.

  • 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. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $58. However, be on the lookout for offers from American Airlines and Delta, 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 $200, 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 $136 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 July is currently the most expensive (average of $120). 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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Alternative routes for Chesapeake to Fort Myers

See prices for flight routes from nearby airports that may be better suited for you.
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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 février 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$79Average$194FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$106Average$182FlexibilityNo cancel feeOn-time62%
DeltaCheapest$113Average$314FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$216Average$379FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$219Average$404FlexibilityNo cancel feeOn-time71%

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