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$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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Fort Myers Beach are usually found in August or January, booked 46 days in advance, depart on a Tuesday or Wednesday 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 July 31, 2025.

Round-trip from

$91
(Kiwi.com)

One-way from

$67
(Booking.com)

Popular in

March

Cheapest in

August

Average price

$256
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. 12% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/29. 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 9/125:31 pmORD - RSW
Nonstop2h 53mSpirit Airlines
Thu 9/187:00 amRSW - ORD
Nonstop3h 13mSpirit Airlines
Deal found 7/29$91
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 9/202:44 pmORD - RSW
Nonstop3h 06mAmerican Airlines
Tue 9/231:36 pmRSW - ORD
Nonstop3h 16mAmerican Airlines
Deal found 7/30$157
This Southwest deal was found by Cheapflights users on 7/29. 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.
Tue 9/26:20 pmMDW - RSW
Nonstop2h 45mSouthwest
Wed 9/109:15 amRSW - MDW
Nonstop2h 50mSouthwest
Deal found 7/29$157
This Booking.com deal was found by Cheapflights users on 7/28. 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.
Sun 8/3110:43 amORD - RSW
1 stop9h 47mMultiple Airlines
Wed 9/37:00 amRSW - ORD
Nonstop3h 07mMultiple Airlines
Deal found 7/28$160
This Delta deal was found by Cheapflights users on 7/30. 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.
Tue 10/216:00 amMDW - RSW
1 stop4h 50mDelta
Mon 10/276:41 pmRSW - MDW
1 stop4h 33mDelta
Deal found 7/30$217
This Priceline deal was found by Cheapflights users on 7/29. 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 8/3111:03 amMDW - RSW
1 stop6h 21mFrontier
Sun 9/147:24 pmRSW - MDW
1 stop4h 56mFrontier
Deal found 7/29$239

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 July 31, 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

Fri 9/12

5:31 pm-9:24 pm

Nonstop2h 53m

Fort Myers SW Florida Intl

Thu 9/18

7:00 am-9:13 am

Nonstop3h 13m

$91

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 9/20

2:44 pm-6:50 pm

Nonstop3h 06m

Fort Myers SW Florida Intl

Tue 9/23

1:36 pm-3:52 pm

Nonstop3h 16m

$157

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 9/2

6:20 pm-10:05 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Wed 9/10

9:15 am-11:05 am

Nonstop2h 50m

$157

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 10/21

6:00 am-11:50 am

1 stop4h 50m

Fort Myers SW Florida Intl

Sun 10/26

5:38 am-9:40 am

1 stop5h 02m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sun 8/31

11:03 am-6:24 pm

1 stop6h 21m

Fort Myers SW Florida Intl

Sun 9/14

7:24 pm-11:20 pm

1 stop4h 56m

$239

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 12/4

7:00 am-10:51 am

Nonstop2h 51m

$63

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 10/7

9:16 am-1:19 pm

Nonstop3h 03m

$79

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 11/19

6:15 pm-10:10 pm

Nonstop2h 55m

$79

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Mon 9/1

6:00 am-11:55 am

1 stop4h 55m

$102

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 10/7

5:20 am-11:50 am

1 stop5h 30m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 15 results
1
2

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 July 25, 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 July 31, 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. Monday 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 July 31, 2025.

The most flights from CHI to FM9 are scheduled on a Thursday (17 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 July 31, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United 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
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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.
JetBlue
7.3
Good
2,914 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

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.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $67. United Airlines flights start at $79 while deals on Southwest start at $79 one-way.

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

    Consider Air New Zealand (88%), Qatar Airways (80%) or Alaska Airlines (80%) 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 $348 for a flight from Chicago to Fort Myers Beach. The cheapest flight overall is $45 while the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl) is currently priced at $57.

  • 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 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$127FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$69Average$382FlexibilityNo cancel feeOn-time83%
Allegiant AirCheapest$74Average$187FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$83Average$319FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$162Average$338FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$173Average$429FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$176Average$399FlexibilityNo cancel feeOn-time69%
DeltaCheapest$196Average$369FlexibilityNo cancel feeOn-timeN/A

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