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$70+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — RSW
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 June, 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 junio 12, 2025.

Round-trip from

$132
(Priceline)

One-way from

$70
(Priceline)

Popular in

September

Cheapest in

January

Average price

$199
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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Highest demand for flights based on searches. 5% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junio 12, 2025.

This Priceline deal was found by Cheapflights users on 6/11. 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.
jue. 7/101:51 pmORF - RSW
Nonstop2h 23mBreeze Airways
dom. 7/136:45 amRSW - ORF
Nonstop2h 09mBreeze Airways
Deal found 6/11$132
This JetBlue deal was found by Cheapflights users on 6/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/175:57 pmORF - RSW
1 stop6h 02mJetBlue
lun. 7/2111:13 amRSW - ORF
1 stop5h 49mJetBlue
Deal found 6/9$219
This Delta deal was found by Cheapflights users on 6/11. 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.
jue. 7/107:58 pmORF - RSW
1 stop4h 47mDelta
dom. 7/137:55 pmRSW - ORF
1 stop4h 44mDelta
Deal found 6/11$237
This American Airlines deal was found by Cheapflights users on 6/12. 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.
dom. 8/35:03 amORF - RSW
1 stop4h 04mAmerican Airlines
mié. 8/611:57 amRSW - ORF
1 stop7h 14mAmerican Airlines
Deal found 6/12$245
This Mytrip deal was found by Cheapflights users on 6/10. 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.
jue. 7/106:30 pmORF - RSW
1 stop23h 55mSpirit Airlines
dom. 7/137:20 pmRSW - ORF
1 stop22h 15mSpirit Airlines
Deal found 6/10$272
This Mytrip deal was found by Cheapflights users on 6/10. 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.
jue. 7/106:30 pmORF - RSW
1 stop23h 55mMultiple Airlines
dom. 7/136:45 amRSW - ORF
Nonstop2h 09mMultiple Airlines
Deal found 6/10$273
This Southwest deal was found by Cheapflights users on 6/10. 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.
mié. 7/95:25 amORF - RSW
2 stops9h 55mSouthwest
dom. 7/135:30 amRSW - ORF
1 stop4h 40mSouthwest
Deal found 6/10$327
This United Airlines deal was found by Cheapflights users on 6/11. 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.
mar. 8/58:10 pmORF - RSW
3 stops18h 52mUnited Airlines
sáb. 8/95:20 pmRSW - ORF
1 stop6h 20mUnited Airlines
Deal found 6/11$427

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 junio 12, 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

jue. 7/10

1:51 pm-4:14 pm

Nonstop2h 23m

Fort Myers SW Florida Intl

dom. 7/13

6:45 am-8:54 am

Nonstop2h 09m

$132

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

jue. 7/17

5:57 pm-11:59 pm

1 stop6h 02m

Fort Myers SW Florida Intl

lun. 7/21

11:13 am-5:02 pm

1 stop5h 49m

$219

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

jue. 7/10

7:58 pm-12:45 am

1 stop4h 47m

Fort Myers SW Florida Intl

dom. 7/13

7:55 pm-12:39 am

1 stop4h 44m

$237

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

dom. 8/3

5:03 am-9:07 am

1 stop4h 04m

Fort Myers SW Florida Intl

mié. 8/6

11:57 am-7:11 pm

1 stop7h 14m

$245

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

jue. 7/10

6:30 pm-6:25 pm

1 stop23h 55m

Fort Myers SW Florida Intl

dom. 7/13

7:20 pm-5:35 pm

1 stop22h 15m

$272

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

jue. 7/10

6:30 pm-6:25 pm

1 stop23h 55m

Fort Myers SW Florida Intl

dom. 7/13

6:45 am-8:54 am

Nonstop2h 09m

$273

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

mié. 7/9

5:25 am-3:20 pm

2 stops9h 55m

Fort Myers SW Florida Intl

dom. 7/13

5:30 am-10:10 am

1 stop4h 40m

$327

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

mar. 8/5

8:10 pm-3:02 pm

3 stops18h 52m

Fort Myers SW Florida Intl

sáb. 8/9

5:20 pm-11:40 pm

1 stop6h 20m

$427

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

mar. 7/15

2:24 pm-7:09 pm

1 stop4h 45m

$70

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

dom. 7/6

5:57 pm-11:59 pm

1 stop6h 02m

$108

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 15 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 June 9, 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 $297). 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 junio 12, 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 8, 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.

Rainfall in Fort Myers by month

Plan your trip to Fort Myers by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Fort Myers ranges from 1.7 - 10.1 inches per month. June is typically the wettest month, when rainfall can reach 10.1 in. December is typically the driest time to visit Fort Myers when rainfall is around 1.7 in.

Temperature in Fort Myers by month

Plan your trip to Fort Myers by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Fort Myers, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).

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 junio 12, 2025.
Read through reviews of airlines operating flights from Chesapeake to Fort Myers, such as Breeze Airways, Southwest and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
178 reviews

Boarding

8.3

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Entertainment

6.6

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
178 reviews
Breeze Airways
8.1
Very good
178 reviews

Boarding

8.3

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Entertainment

6.6

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Southwest
8.0
Very good
4,287 reviews
Breeze Airways
8.1
Very good
178 reviews

Boarding

8.3

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Entertainment

6.6

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,950 reviews
Breeze Airways
8.1
Very good
178 reviews

Boarding

8.3

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Entertainment

6.6

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,790 reviews
Breeze Airways
8.1
Very good
178 reviews

Boarding

8.3

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Entertainment

6.6

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
JetBlue
7.3
Good
2,925 reviews
Breeze Airways
8.1
Very good
178 reviews

Boarding

8.3

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Entertainment

6.6

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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 $70. However, be on the lookout for offers from JetBlue 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 $144, our data shows the cheapest flight currently is $86. When looking at the most popular route, (Norfolk - Fort Myers SW Florida Intl), you can expect to pay $132 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 $297). 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 Chesapeake?

Book flights to Chesapeake if you plan to visit one of these locations
North Fort Myers
Sanibel
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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$99Average$201FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$107Average$278FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$313FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$198Average$388FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$226Average$379FlexibilityNo cancel feeOn-time63%

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