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$79+ 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 49 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 June 16, 2025.

Round-trip from

$155
(FlightHub)

One-way from

$79
(Southwest)

Popular in

March

Cheapest in

August

Average price

$260
From Chicago (CHI) to Fort Myers Beach
Search Deals
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 ($37 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 June 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 June 16, 2025.

This FlightHub deal was found by Cheapflights users on 6/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/28:00 amORD - RSW
Nonstop2h 53mSpirit Airlines
Mon 7/79:04 amRSW - ORD
Nonstop3h 09mSpirit Airlines
Deal found 6/16$155
This Southwest deal was found by Cheapflights users on 6/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/209:05 amMDW - RSW
Nonstop2h 45mSouthwest
Wed 8/279:15 amRSW - MDW
Nonstop2h 50mSouthwest
Deal found 6/15$157
This American Airlines deal was found by Cheapflights users on 6/16. 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.
Sun 8/106:50 amORD - RSW
Nonstop2h 52mAmerican Airlines
Fri 8/1511:48 amRSW - ORD
Nonstop3h 17mAmerican Airlines
Deal found 6/16$159
This United Airlines deal was found by Cheapflights users on 6/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/27:11 amORD - RSW
Nonstop3h 05mUnited Airlines
Sat 8/167:15 amRSW - ORD
Nonstop3h 14mUnited Airlines
Deal found 6/14$167
This Booking.com deal was found by Cheapflights users on 6/14. 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.
Sat 7/56:09 pmORD - RSW
1 stop14h 39mMultiple Airlines
Wed 7/98:17 pmRSW - ORD
Nonstop3h 15mMultiple Airlines
Deal found 6/14$176
This JetBlue deal was found by Cheapflights users on 6/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/68:34 amORD - RSW
1 stop8h 31mJetBlue
Sat 9/1311:30 amRSW - ORD
1 stop7h 54mJetBlue
Deal found 6/16$211
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/98:30 amORD - RSW
1 stop7h 41mDelta
Fri 7/187:52 pmRSW - ORD
1 stop5h 17mDelta
Deal found 6/15$217
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/910:30 amMDW - RSW
1 stop7h 11mDelta
Sat 7/195:46 pmRSW - MDW
1 stop4h 56mDelta
Deal found 6/15$217
This FlightHub deal was found by Cheapflights users on 6/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/76:20 amMDW - RSW
1 stop11h 00mFrontier
Sun 8/107:16 pmRSW - MDW
1 stop5h 01mFrontier
Deal found 6/14$244
This Sun Country Air deal was found by Cheapflights users on 6/16. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2411:42 amORD - RSW
1 stop22h 01mSun Country Air
Fri 11/286:15 amRSW - ORD
1 stop27h 47mSun Country Air
Deal found 6/16$265
This Southwest deal was found by Cheapflights users on 6/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/71:50 pmORD - RSW
1 stop7h 50mSouthwest
Fri 8/157:15 amRSW - ORD
1 stop5h 35mSouthwest
Deal found 6/15$267
This FlightHub deal was found by Cheapflights users on 6/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/175:01 amORD - RSW
1 stop12h 19mFrontier
Sun 7/207:17 pmRSW - ORD
1 stop16h 08mFrontier
Deal found 6/14$296

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 June 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

Wed 7/2

8:00 am-11:53 am

Nonstop2h 53m

Fort Myers SW Florida Intl

Mon 7/7

9:04 am-11:13 am

Nonstop3h 09m

$155

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 8/20

9:05 am-12:50 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Wed 8/27

9:15 am-11:05 am

Nonstop2h 50m

$157

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 8/10

6:50 am-10:42 am

Nonstop2h 52m

Fort Myers SW Florida Intl

Fri 8/15

11:48 am-2:05 pm

Nonstop3h 17m

$159

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 8/2

7:11 am-11:16 am

Nonstop3h 05m

Fort Myers SW Florida Intl

Sat 8/16

7:15 am-9:29 am

Nonstop3h 14m

$167

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 7/5

6:09 pm-9:48 am

1 stop14h 39m

Fort Myers SW Florida Intl

Wed 7/9

8:17 pm-10:32 pm

Nonstop3h 15m

$176

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 9/6

8:34 am-6:05 pm

1 stop8h 31m

Fort Myers SW Florida Intl

Sat 9/13

11:30 am-6:24 pm

1 stop7h 54m

$211

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 7/9

8:30 am-5:11 pm

1 stop7h 41m

Fort Myers SW Florida Intl

Fri 7/18

7:52 pm-12:09 am

1 stop5h 17m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 7/9

9:24 am-5:11 pm

1 stop6h 47m

Fort Myers SW Florida Intl

Tue 7/15

5:45 pm-9:42 pm

1 stop4h 57m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Thu 8/7

6:20 am-6:20 pm

1 stop11h 00m

Fort Myers SW Florida Intl

Sun 8/10

7:16 pm-11:17 pm

1 stop5h 01m

$244

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Mon 11/24

11:42 am-10:43 am

1 stop22h 01m

Fort Myers SW Florida Intl

Fri 11/28

6:15 am-9:02 am

1 stop27h 47m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

Showing 1-10 of 24 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 June 13, 2025.

Booking 49 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 $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 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 June 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 June 9, 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 June 16, 2025.

The most flights from CHI to FM9 are scheduled on a Saturday (18 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (14 on average).

Rainfall in Fort Myers Beach by month

Plan your trip to Fort Myers Beach by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Fort Myers Beach 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 Beach when rainfall is around 1.7 in.

Temperature in Fort Myers Beach by month

Plan your trip to Fort Myers Beach by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Fort Myers Beach, 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 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 June 16, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Chicago to Fort Myers Beach. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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
7,963 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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
8,801 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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
2,922 reviews
Southwest
8.0
Very good
4,278 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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
4,278 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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 Southwest, which is currently one of the cheapest options available, starting at $79. United Airlines flights start at $80 while deals on Spirit Airlines start at $82 one-way.

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

    Consider Frontier (100%), Spirit Airlines (91%) or Air New Zealand (88%) 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 $567 for a flight from Chicago to Fort Myers Beach. The cheapest flight overall is $61 while the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl) is currently priced at $98.

  • 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 $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.

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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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$127FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$74Average$191FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$74Average$258FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$95Average$386FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$171Average$342FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$194Average$441FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$391FlexibilityNo cancel feeOn-timeN/A

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