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$71+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — RSW
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
1 adult, Economy
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The best prices from Chesapeake to Fort Myers SW Florida Intl are usually found in January or November, booked 48 days in advance, depart on a Thursday or Monday 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 February 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$100
(Priceline)

One-way from

$71
(Priceline)

Popular in

September

Cheapest in

January

Average price

$297
Provider with most accurate pricing for Norfolk-Fort Myers SW Florida Intl flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Fort Myers SW Florida Intl flights.
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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. 7% potential increase in price ($22 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 February 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 February 23, 2025.

This Priceline deal was found by Cheapflights users on 2/22. 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.
Sat 5/36:44 pmORF - RSW
1 stop6h 20mSpirit Airlines
Tue 5/611:29 amRSW - ORF
1 stop6h 20mSpirit Airlines
Deal found 2/22$100
This Breeze Airways deal was found by Cheapflights users on 2/22. 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.
Fri 3/75:44 pmORF - RSW
Nonstop2h 26mBreeze Airways
Mon 3/178:50 pmRSW - ORF
Nonstop2h 09mBreeze Airways
Deal found 2/22$194
This Mytrip deal was found by Cheapflights users on 2/22. 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.
Sun 4/134:05 pmORF - RSW
2 stops30h 39mMultiple Airlines
Sun 4/208:34 pmRSW - ORF
1 stop21h 15mMultiple Airlines
Deal found 2/22$223
This American Airlines deal was found by Cheapflights users on 2/22. 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 3/276:16 pmORF - RSW
1 stop6h 37mAmerican Airlines
Tue 4/11:45 pmRSW - ORF
1 stop3h 41mAmerican Airlines
Deal found 2/22$237
This United Airlines deal was found by Cheapflights users on 2/22. 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.
Mon 3/106:00 amORF - RSW
1 stop5h 46mUnited Airlines
Fri 3/146:15 pmRSW - ORF
1 stop5h 08mUnited Airlines
Deal found 2/22$307
This Southwest deal was found by Cheapflights users on 2/22. 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.
Sat 5/35:30 pmORF - RSW
1 stop4h 25mSouthwest
Tue 5/68:15 amRSW - ORF
2 stops8h 50mSouthwest
Deal found 2/22$327
This Delta deal was found by Cheapflights users on 2/21. 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.
Fri 2/284:19 pmORF - RSW
1 stop6h 52mDelta
Thu 3/133:05 pmRSW - ORF
1 stop7h 21mDelta
Deal found 2/21$467

Find flights from Chesapeake to Fort Myers within your budget

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 February 23, 2025.

Fly from

Chesapeake

Fly to

Fort Myers

Route

Depart

Return

Price

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Sat 5/3

6:44 pm-1:04 am

1 stop6h 20m

Fort Myers SW Florida Intl

Tue 5/6

11:29 am-5:49 pm

1 stop6h 20m

$100

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Fri 3/7

5:44 pm-8:10 pm

Nonstop2h 26m

Fort Myers SW Florida Intl

Mon 3/17

8:50 pm-10:59 pm

Nonstop2h 09m

$194

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Sun 4/13

4:05 pm-10:44 pm

2 stops30h 39m

Fort Myers SW Florida Intl

Sun 4/20

8:34 pm-5:49 pm

1 stop21h 15m

$223

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Thu 3/27

6:16 pm-12:53 am

1 stop6h 37m

Fort Myers SW Florida Intl

Tue 4/1

1:45 pm-5:26 pm

1 stop3h 41m

$237

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Mon 3/10

6:00 am-11:46 am

1 stop5h 46m

Fort Myers SW Florida Intl

Fri 3/14

6:15 pm-11:23 pm

1 stop5h 08m

$307

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Sat 5/3

5:30 pm-9:55 pm

1 stop4h 25m

Fort Myers SW Florida Intl

Tue 5/6

8:15 am-5:05 pm

2 stops8h 50m

$327

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Fri 3/7

7:05 pm-12:36 am

1 stop5h 31m

Fort Myers SW Florida Intl

Mon 3/17

7:49 pm-12:03 am

1 stop4h 14m

$508

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Thu 5/1

11:49 am-2:12 pm

Nonstop2h 23m

$71

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Thu 5/1

6:44 pm-9:52 am

1 stop15h 08m

$97

NorfolkFort Myers

ORF - RSW

ORFRSW

Norfolk

Wed 3/19

6:16 pm-12:53 am

1 stop6h 37m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Showing 1-10 of 13 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.

Travel insights for flights from Chesapeake to Fort Myers

Get recent, data-driven insights about flights from Chesapeake to Fort Myers including ideal travel times, pricing trends, and more.

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 February 14, 2025.

The best time to book flights from Chesapeake to Fort Myers is 48 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 February 23, 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 February 16, 2025.

Travelers seeking maximum savings on their Chesapeake to Fort Myers flight should consider departing on Friday afternoons when fares are most often at their lowest. Friday at noon 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 February 23, 2025.
Read through reviews of airlines operating flights from Chesapeake to Fort Myers, such as Southwest, Breeze Airways and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,387 reviews

Entertainment

7.6

Comfort

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,387 reviews
Southwest
8.1
Very good
4,387 reviews

Entertainment

7.6

Comfort

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Breeze Airways
8.1
Very good
150 reviews
Southwest
8.1
Very good
4,387 reviews

Entertainment

7.6

Comfort

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,191 reviews
Southwest
8.1
Very good
4,387 reviews

Entertainment

7.6

Comfort

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,746 reviews
Southwest
8.1
Very good
4,387 reviews

Entertainment

7.6

Comfort

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,387 reviews

Entertainment

7.6

Comfort

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 6 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 $71. However, be on the lookout for offers from Spirit Airlines 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 $239, our data shows the cheapest flight currently is $64. When looking at the most popular route, (Norfolk - Fort Myers SW Florida Intl), you can expect to pay $125 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
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 6 airlines flying from Chesapeake to Fort Myers

Discover the top 6 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 February 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$42Average$113FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$90Average$197FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$176Average$301FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$186Average$357FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$248Average$396FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$344Average$472FlexibilityNo cancel feeOn-time69%
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