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$43+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Fort Myers Beach are usually found in August or September, booked 87 days in advance, depart on a Tuesday or Wednesday and return on a Friday

Cheap 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 February 4, 2026.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/15:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Fri 3/67:51 pm
RSW
-
ORD
Nonstop3h 10m
Spirit Airlines
Deal found 2/2$91
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.
Sat 2/289:30 am
ORD
-
RSW
Nonstop3h 14m
Multiple Airlines
Mon 3/96:00 am
RSW
-
ORD
Nonstop3h 13m
Multiple Airlines
Deal found 2/1$93
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.
Thu 3/56:30 am
ORD
-
RSW
Nonstop3h 09m
Multiple Airlines
Wed 3/189:54 pm
RSW
-
ORD
Nonstop3h 05m
Multiple Airlines
Deal found 2/3$94
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/211:37 pm
ORD
-
RSW
Nonstop3h 14m
Multiple Airlines
Sat 2/286:00 am
RSW
-
ORD
Nonstop3h 13m
Multiple Airlines
Deal found 2/2$95
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.
Sun 3/16:30 am
ORD
-
RSW
Nonstop3h 09m
Multiple Airlines
Mon 3/97:51 pm
RSW
-
ORD
Nonstop3h 10m
Multiple Airlines
Deal found 2/2$96
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.
Mon 3/27:20 am
ORD
-
RSW
Nonstop2h 56m
Multiple Airlines
Thu 3/511:34 am
RSW
-
ORD
Nonstop3h 34m
Multiple Airlines
Deal found 2/1$97
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Sun 3/86:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Deal found 2/2$98
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.
Tue 3/35:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Sat 3/147:35 am
RSW
-
ORD
Nonstop3h 15m
Spirit Airlines
Deal found 2/3$99
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/285:05 am
ORD
-
RSW
1 stop5h 56m
Multiple Airlines
Sat 3/76:00 am
RSW
-
ORD
Nonstop3h 13m
Multiple Airlines
Deal found 2/2$100
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.
Mon 3/27:20 am
ORD
-
RSW
Nonstop2h 56m
Spirit Airlines
Mon 3/96:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Deal found 2/2$101
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Sun 2/226:30 am
ORD
-
RSW
Nonstop3h 09m
Multiple Airlines
Tue 2/246:00 am
RSW
-
ORD
Nonstop3h 13m
Multiple Airlines
Deal found 2/4$102
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/117:00 am
ORD
-
RSW
Nonstop3h 01m
Spirit Airlines
Wed 2/186:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Deal found 2/3$103

Find 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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$91
(Cheapflightsfares)

One-way from

$43
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$254
Provider with most accurate pricing for Chicago (CHI)-Fort Myers SW Florida Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Fort Myers SW Florida Intl flights.
Search Deals
From Chicago (CHI) to Fort Myers Beach
Search Deals
One-way flight from Chicago (CHI) to Fort Myers Beach
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 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 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 February 4, 2026.
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

MDW - RSW

MDWRSW

Chicago Midway

Sat 3/7

8:35 pm-12:25 am

Nonstop2h 50m

Fort Myers SW Florida Intl

Wed 3/11

6:15 am-8:15 am

Nonstop3h 00m

$174

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 2/24

5:53 pm-12:33 am

1 stop5h 40m

Fort Myers SW Florida Intl

Thu 3/5

6:35 am-10:14 am

1 stop4h 39m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Mon 3/9

9:02 am-1:10 pm

Nonstop3h 08m

Fort Myers SW Florida Intl

Mon 3/16

12:29 pm-2:55 pm

Nonstop3h 26m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Mon 3/9

10:42 am-2:49 pm

Nonstop3h 07m

Fort Myers SW Florida Intl

Thu 3/12

7:00 am-9:25 am

Nonstop3h 25m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 3/4

9:52 am-5:18 pm

1 stop6h 26m

Fort Myers SW Florida Intl

Tue 3/17

5:59 pm-11:54 pm

1 stop6h 55m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 2/28

6:00 pm-9:45 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Sat 3/7

7:40 pm-9:40 pm

Nonstop3h 00m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 2/25

9:52 am-5:18 pm

1 stop6h 26m

Fort Myers SW Florida Intl

Sat 3/7

7:50 pm-11:56 pm

1 stop5h 06m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 3/3

12:45 pm-8:43 pm

1 stop6h 58m

Fort Myers SW Florida Intl

Tue 3/10

4:30 pm-10:31 pm

1 stop7h 01m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Mon 2/23

9:48 am-5:18 pm

1 stop6h 30m

Fort Myers SW Florida Intl

Thu 3/5

5:35 am-10:14 am

1 stop5h 39m

$218

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Mon 3/2

10:49 am-5:18 pm

1 stop5h 29m

Fort Myers SW Florida Intl

Tue 3/10

4:30 pm-10:31 pm

1 stop7h 01m

$218

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 43 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 January 30, 2026.

Booking 87 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, February is the cheapest month in which you can book a flight from Chicago to Fort Myers Beach (average of $50). Flying from Chicago to Fort Myers Beach in November is currently the most expensive (average of $133). 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 February 4, 2026.

One of the essential ways to save on airfare from Chicago to Fort Myers Beach is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 24% on airfare.

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 January 31, 2026.

Travelers seeking maximum savings on their Chicago to Fort Myers Beach flight should consider departing on Wednesday 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 February 4, 2026.

The most flights from CHI to FM9 are scheduled on a Monday (23 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 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 February 4, 2026.
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
4,274 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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
4,274 reviews
Southwest
8.0
Very good
4,274 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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
9,236 reviews
Southwest
8.0
Very good
4,274 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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
11,222 reviews
Southwest
8.0
Very good
4,274 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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
8,411 reviews
Southwest
8.0
Very good
4,274 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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
5.7
Fair
3,052 reviews
Southwest
8.0
Very good
4,274 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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. Southwest provides one of the quickest options available for as low as $174. The distance between Chicago and Fort Myers Beach is about 1106 mi. This flight may include one or multiple stops.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $30. Spirit Airlines flights start at $38 while deals on American Airlines start at $78 one-way.

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

    Consider Air New Zealand (87%), Emirates (83%) or SWISS (83%) 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 $536 for a flight from Chicago to Fort Myers Beach. The cheapest flight overall is $36 while the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl) is currently priced at $54.

  • 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, February is the cheapest month in which you can book a flight from Chicago to Fort Myers Beach (average of $50). Flying from Chicago to Fort Myers Beach in November is currently the most expensive (average of $133). 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 8 airlines flying from Chicago to Fort Myers Beach

Discover the top 8 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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$32Average$141FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$69Average$208FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$99Average$196FlexibilityNo cancel feeOn-time88%
DeltaCheapest$129Average$406FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$143Average$217FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$351FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$159Average$357FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$171Average$373FlexibilityNo cancel feeOn-time63%

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