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Fort Myers Beach

$63+ Cheap flights from Chicago (CHI) to Fort Myers Beach, FL

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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Fort Myers Beach are usually found in August or July, booked 46 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap flight deals from Chicago to Fort Myers Beach

Keep the following information in mind while searching for Chicago to Fort Myers Beach flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$119
(Cheapflightsfares)

One-way from

$63
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$255
From Chicago (CHI) to Fort Myers Beach
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One-way flight from Chicago (CHI) to Fort Myers Beach
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Highest demand for flights based on searches. 11% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Fort Myers Beach

Cheapest flights from Chicago to Fort Myers Beach
Explore the most affordable flight options available from Chicago to Fort Myers Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/136:16 pmORD - RSW
Nonstop2h 53mSpirit Airlines
lun. 10/206:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Deal found 9/14$119
This Booking.com deal was found by Cheapflights users on 9/14. 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.
jue. 12/47:00 amORD - RSW
Nonstop2h 51mSpirit Airlines
lun. 12/811:56 amRSW - ORD
Nonstop3h 10mSpirit Airlines
Deal found 9/14$120
This Gotogate deal was found by Cheapflights users on 9/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/176:16 pmORD - RSW
Nonstop2h 53mSpirit Airlines
dom. 10/196:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Deal found 9/15$121
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
mié. 12/37:28 pmORD - RSW
Nonstop2h 55mSpirit Airlines
sáb. 12/137:59 pmRSW - ORD
Nonstop3h 10mSpirit Airlines
Deal found 9/15$127
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
dom. 10/124:51 pmORD - RSW
Nonstop2h 50mSpirit Airlines
jue. 10/236:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Deal found 9/15$128
This Priceline deal was found by Cheapflights users on 9/14. 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. 10/95:05 amORD - RSW
1 stop6h 11mMultiple Airlines
dom. 10/126:40 amRSW - ORD
Nonstop2h 54mMultiple Airlines
Deal found 9/14$132
This Priceline deal was found by Cheapflights users on 9/15. 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.
vie. 10/318:26 amORD - RSW
1 stop11h 07mMultiple Airlines
lun. 11/36:22 amRSW - ORD
Nonstop2h 54mMultiple Airlines
Deal found 9/15$138
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/106:16 pmORD - RSW
Nonstop2h 53mSpirit Airlines
dom. 10/126:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Deal found 9/15$139
This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/67:00 amORD - RSW
Nonstop2h 51mSpirit Airlines
lun. 11/1011:56 amRSW - ORD
Nonstop3h 10mSpirit Airlines
Deal found 9/14$140
This Orbitz deal was found by Cheapflights users on 9/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/137:00 amORD - RSW
Nonstop2h 51mMultiple Airlines
dom. 11/161:13 pmRSW - ORD
1 stop11h 58mMultiple Airlines
Deal found 9/14$143
This Priceline deal was found by Cheapflights users on 9/14. 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. 10/306:20 amMDW - RSW
1 stop4h 52mFrontier
dom. 11/21:14 pmRSW - MDW
1 stop9h 49mFrontier
Deal found 9/14$143
This Booking.com deal was found by Cheapflights users on 9/14. 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.
jue. 10/305:11 amORD - RSW
1 stop6h 01mFrontier
dom. 11/21:14 pmRSW - ORD
1 stop11h 57mFrontier
Deal found 9/14$144

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Fort Myers Beach 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 septiembre 16, 2025.
Use the filters below to find and compare flights from Chicago to Fort Myers Beach that are best for you.

Fly from

Chicago

Fly to

Fort Myers Beach

Route

Depart

Return

Price

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

lun. 10/13

7:15 am-11:18 am

Nonstop3h 03m

Fort Myers SW Florida Intl

mié. 10/15

4:35 pm-6:50 pm

Nonstop3h 15m

$169

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

mié. 12/10

8:20 am-12:10 pm

Nonstop2h 50m

Fort Myers SW Florida Intl

mar. 12/16

5:10 pm-8:40 pm

1 stop4h 30m

$187

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

mié. 10/8

5:45 am-12:00 pm

1 stop5h 15m

Fort Myers SW Florida Intl

mié. 10/15

6:05 am-7:55 am

Nonstop2h 50m

$188

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

sáb. 10/25

5:30 pm-9:10 pm

Nonstop2h 40m

Fort Myers SW Florida Intl

sáb. 11/1

4:20 pm-10:35 pm

1 stop7h 15m

$191

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

jue. 10/30

9:45 am-8:10 pm

2 stops9h 25m

Fort Myers SW Florida Intl

mar. 11/4

6:30 am-8:25 am

Nonstop2h 55m

$196

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

sáb. 10/25

6:00 am-2:35 pm

1 stop7h 35m

Fort Myers SW Florida Intl

sáb. 11/1

12:39 pm-2:53 pm

Nonstop3h 14m

$198

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

sáb. 2/7

4:10 pm-8:12 pm

Nonstop3h 02m

Fort Myers SW Florida Intl

mié. 2/11

1:45 pm-6:37 pm

1 stop5h 52m

$198

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

mar. 12/9

6:15 pm-10:10 pm

Nonstop2h 55m

Fort Myers SW Florida Intl

lun. 12/15

6:30 am-8:25 am

Nonstop2h 55m

$206

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

mar. 12/23

4:25 pm-10:50 pm

1 stop5h 25m

Fort Myers SW Florida Intl

mar. 12/30

11:20 am-1:30 pm

Nonstop3h 10m

$207

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

vie. 12/12

5:35 am-9:20 am

Nonstop2h 45m

Fort Myers SW Florida Intl

jue. 12/18

8:50 pm-10:45 pm

Nonstop2h 55m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 41 results
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Best time to book a flight from Chicago to Fort Myers Beach

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

How far ahead should I book a flight from Chicago to Fort Myers Beach?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Fort Myers Beach. Price data was last updated on September 12, 2025.

Booking 46 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Fort Myers Beach. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Fort Myers Beach (average of $205). Flying from Chicago to Fort Myers Beach in June is currently the most expensive (average of $290). 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 CHI to FM9?

Find hourly flight availability from Chicago to Fort Myers Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 16, 2025.

When flying from Chicago to Fort Myers Beach, 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 Chicago to Fort Myers Beach?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Fort Myers Beach. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Fort Myers Beach flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Fort Myers Beach

Explore weekly flight availability from Chicago to Fort Myers Beach. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated septiembre 16, 2025.

The most flights from CHI to FM9 are scheduled on a Monday (16 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from Chicago to Fort Myers Beach?

Reviews of airlines servicing Fort Myers Beach

Get insights into the airlines that provide service to Fort Myers Beach. 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 Beach. Reviews last updated septiembre 16, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Chicago to Fort Myers Beach by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Spirit Airlines
6.3
Okay
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Fort Myers Beach. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Fort Myers Beach?

    A quick flight from Chicago to Fort Myers Beach can take about 2h 50m. United Airlines provides one of the quickest options available for as low as $187. The distance between Chicago and Fort Myers Beach is about 1106 mi. This flight may include one or multiple stops.

  • What are the most reliable airlines from Chicago to Fort Myers Beach?

    Consider Air New Zealand (89%), Air Canada (84%) or Alaska Airlines (81%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Fort Myers Beach.

  • What are the cheapest flights from Chicago to Fort Myers Beach?

    On average you can expect to pay $542 for a flight from Chicago to Fort Myers Beach. The cheapest flight overall is $49 while the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl) is currently priced at $119.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Fort Myers Beach 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 Chicago to Fort Myers Beach?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Fort Myers Beach (average of $205). Flying from Chicago to Fort Myers Beach in June is currently the most expensive (average of $290). 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 7 airlines flying from Chicago to Fort Myers Beach

Discover the top 7 airlines that operate flights from Chicago to Fort Myers Beach. 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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$127FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$74Average$176FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$84Average$302FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$160Average$335FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$174Average$418FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$176Average$395FlexibilityNo cancel feeOn-time69%
DeltaCheapest$178Average$350FlexibilityNo cancel feeOn-timeN/A

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