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Chesapeake

$105+ Cheap flights from Fort Myers (RSW) to Chesapeake, VA

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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — RIC
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
1 adult, Economy
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Cheap flight deals from Fort Myers to Chesapeake

Cheapest flights from Fort Myers to Chesapeake
Explore the most affordable flight options available from Fort Myers to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 24, 2026.

This Breeze Airways deal was found by Cheapflights users on 3/19. 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 8/137:45 am
RSW
-
ORF
Nonstop2h 13m
Breeze Airways
Mon 8/1711:25 am
ORF
-
RSW
1 stop4h 41m
Breeze Airways
Deal found 3/19$202
This Mytrip deal was found by Cheapflights users on 3/22. 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.
Thu 4/1610:15 am
RSW
-
ORF
Nonstop2h 09m
Breeze Airways
Thu 4/237:05 am
ORF
-
RSW
Nonstop2h 30m
Breeze Airways
Deal found 3/22$227
This Booking.com deal was found by Cheapflights users on 3/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:45 am
RSW
-
ORF
Nonstop2h 13m
Breeze Airways
Sun 5/104:09 pm
ORF
-
RSW
1 stop7h 46m
Breeze Airways
Deal found 3/22$233
This Kiwi.com deal was found by Cheapflights users on 3/19. 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.
Fri 4/1711:48 am
RSW
-
ORF
2 stops22h 44m
Multiple Airlines
Sun 4/197:05 am
ORF
-
RSW
Nonstop2h 30m
Multiple Airlines
Deal found 3/19$240
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:17 pm
RSW
-
ORF
2 stops21h 35m
Multiple Airlines
Thu 4/237:05 am
ORF
-
RSW
Nonstop2h 30m
Multiple Airlines
Deal found 3/22$250
This Priceline deal was found by Cheapflights users on 3/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/510:15 am
RSW
-
ORF
Nonstop2h 09m
Multiple Airlines
Thu 4/911:31 am
ORF
-
RSW
1 stop7h 10m
Multiple Airlines
Deal found 3/21$251
This Booking.com deal was found by Cheapflights users on 3/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:45 am
RSW
-
ORF
Nonstop2h 13m
Breeze Airways
Sun 6/1410:38 am
ORF
-
RSW
Nonstop2h 25m
Breeze Airways
Deal found 3/20$252
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:54 pm
RSW
-
ORF
1 stop21h 23m
Multiple Airlines
Mon 5/1812:06 pm
ORF
-
RSW
2 stops24h 18m
Multiple Airlines
Deal found 3/22$254
This American Airlines deal was found by Cheapflights users on 3/19. 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.
Tue 4/148:37 am
RSW
-
ORF
1 stop6h 54m
American Airlines
Sat 4/187:00 am
ORF
-
RSW
1 stop7h 25m
American Airlines
Deal found 3/19$258
This Mytrip deal was found by Cheapflights users on 3/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/510:15 am
RSW
-
ORF
Nonstop2h 09m
Breeze Airways
Thu 4/97:05 am
ORF
-
RSW
Nonstop2h 30m
Breeze Airways
Deal found 3/21$271

Find flight deals from Fort Myers to Chesapeake

Keep the following information in mind while searching for Fort Myers to Chesapeake flight deals. Data was last updated March 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$202
(Breeze Airways)

One-way from

$105
(American Airlines)

Popular in

November

Cheapest in

July

Average price

$263
Provider with most accurate pricing for Fort Myers SW Florida Intl-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-Norfolk flights.
Search Deals
From Fort Myers SW Florida Intl to Chesapeake
Search Deals
One-way flight from Fort Myers SW Florida Intl to Chesapeake
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Fort Myers to Chesapeake 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 March 24, 2026.
Use the filters below to find and compare flights from Fort Myers to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Thu 5/7

7:45 am-9:58 am

Nonstop2h 13m

Norfolk

Sun 5/10

10:38 am-1:03 pm

Nonstop2h 25m

$263

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Fri 6/12

7:18 pm-9:08 am

2 stops13h 50m

Norfolk

Sun 6/14

10:38 am-1:03 pm

Nonstop2h 25m

$342

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Thu 6/11

7:45 am-9:58 am

Nonstop2h 13m

Norfolk

Mon 6/15

11:25 am-4:06 pm

1 stop4h 41m

$364

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Thu 5/14

3:28 pm-11:32 pm

1 stop8h 04m

Norfolk

Mon 5/18

6:05 am-11:40 am

1 stop5h 35m

$387

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Wed 5/13

9:20 am-5:50 pm

2 stops8h 30m

Norfolk

Mon 5/18

2:30 pm-9:25 pm

2 stops6h 55m

$392

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Sat 7/25

6:20 am-3:15 pm

2 stops8h 55m

Norfolk

Sat 8/1

11:55 am-7:45 pm

1 stop7h 50m

$412

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Sat 8/1

6:20 am-4:00 pm

2 stops9h 40m

Norfolk

Sat 8/8

9:55 am-7:45 pm

2 stops9h 50m

$417

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Thu 4/16

6:35 am-12:15 pm

2 stops5h 40m

Norfolk

Thu 4/23

2:30 pm-9:50 pm

2 stops7h 20m

$418

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Fri 5/15

6:00 am-10:40 am

1 stop4h 40m

Norfolk

Mon 5/18

6:10 pm-6:15 pm

2 stops24h 05m

$440

Fort MyersNorfolk

RSW - ORF

RSWORF

Fort Myers SW Florida Intl

Fri 4/17

7:01 am-2:20 pm

1 stop7h 19m

Norfolk

Mon 4/20

6:00 am-1:16 pm

1 stop7h 16m

$447

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/20

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

Best time to book a flight from Fort Myers to Chesapeake

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

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

Currently, June is the cheapest month in which you can book a flight from Fort Myers to Chesapeake (average of $79). Flying from Fort Myers to Chesapeake in May is currently the most expensive (average of $153). 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 RSW to C6E?

Find hourly flight availability from Fort Myers to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 24, 2026.

It’s optimal to fly from Fort Myers to Chesapeake at noon. By choosing this option you can save up to 30% on the cost of your flight, compared to a flight in the afternoon.

Reviews of airlines servicing Chesapeake

Get insights into the airlines that provide service to Chesapeake. 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 Chesapeake. Reviews last updated March 24, 2026.
Read reviews from past customers who have flown Breeze Airways,Delta, andAmerican Airlines from Fort Myers to Chesapeake. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
273 reviews

Crew

8.7

Entertainment

6.6

Food

6.6

Overall

8.1

Comfort

8.2

Boarding

8.3

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Breeze Airways
8.1
Very good
273 reviews
Breeze Airways
8.1
Very good
273 reviews

Crew

8.7

Entertainment

6.6

Food

6.6

Overall

8.1

Comfort

8.2

Boarding

8.3

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Delta
7.9
Good
8,321 reviews
Breeze Airways
8.1
Very good
273 reviews

Crew

8.7

Entertainment

6.6

Food

6.6

Overall

8.1

Comfort

8.2

Boarding

8.3

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
American Airlines
7.1
Good
11,491 reviews
Breeze Airways
8.1
Very good
273 reviews

Crew

8.7

Entertainment

6.6

Food

6.6

Overall

8.1

Comfort

8.2

Boarding

8.3

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

Related info for your journey

Find useful and relevant information for your journey from Fort Myers to Chesapeake. 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 from for flights from Fort Myers to Chesapeake?

    For a flight from Fort Myers to Chesapeake, you will be flying from SW Florida Intl. Fort Myers SW Florida Intl (RSW) is just 10.0 mi from the center of the city. SW Florida Intl is the only Fort Myers airport and it handles 0 outbound flights to Chesapeake per day. 3 airlines have flights to Chesapeake from Fort Myers SW Florida Intl on a regular basis.

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

    For as low as $263, Breeze Airways can have you in Chesapeake from Fort Myers in 2h 13m. The distance from Fort Myers to Chesapeake is about 786 mi. This flight may include one or multiple stops.

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

    One-way options have recently been found by users for as low as $59 on Breeze Airways. Other airlines that offer cheap prices include Delta from $104 and Southwest from $135 one-way.

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

    The cheapest flight price from Fort Myers to Chesapeake is $67. On average you can expect to pay $169. The most popular route, (Fort Myers SW Florida Intl - Norfolk), can usually be booked for $254.

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

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

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

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

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

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

    Currently, June is the cheapest month in which you can book a flight from Fort Myers to Chesapeake (average of $79). Flying from Fort Myers to Chesapeake in May is currently the most expensive (average of $153). 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

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Top 3 airlines flying from Fort Myers to Chesapeake

Discover the top 3 airlines that operate flights from Fort Myers to Chesapeake. 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 March 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$72Average$189FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$115Average$288FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$208Average$373FlexibilityNo cancel feeOn-time71%

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