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$77+ 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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Fort Myers Beach are usually found in January or August, 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 April 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$139
(Kiwi.com)

One-way from

$77
(Priceline)

Popular in

March

Cheapest in

January

Average price

$247
Provider with most accurate pricing for Chicago (CHI)-Fort Myers SW Florida Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Fort Myers SW Florida Intl flights.
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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. 8% potential increase in price ($26 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 April 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 April 2, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Thu 4/108:50 pmORD - RSW
Nonstop3h 09mMultiple Airlines
Wed 4/168:52 amRSW - ORD
Nonstop3h 07mMultiple Airlines
Deal found 4/1$139
This Frontier deal was found by Cheapflights users on 4/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/138:50 pmORD - RSW
Nonstop3h 09mFrontier
Sat 4/196:00 amRSW - ORD
Nonstop3h 21mFrontier
Deal found 4/1$142
This FlightHub deal was found by Cheapflights users on 4/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/82:45 pmORD - RSW
Nonstop3h 02mSpirit Airlines
Fri 4/118:52 amRSW - ORD
Nonstop3h 07mSpirit Airlines
Deal found 4/1$157
This American Airlines deal was found by Cheapflights users on 4/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/106:45 pmORD - RSW
Nonstop3h 07mAmerican Airlines
Sat 5/175:40 pmRSW - ORD
Nonstop3h 14mAmerican Airlines
Deal found 4/1$177
This Southwest deal was found by Cheapflights users on 4/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/176:15 pmMDW - RSW
Nonstop2h 50mSouthwest
Sat 5/245:55 amRSW - MDW
Nonstop2h 55mSouthwest
Deal found 4/1$187
This United Airlines deal was found by Cheapflights users on 4/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2510:52 amORD - RSW
Nonstop3h 05mUnited Airlines
Tue 6/34:33 pmRSW - ORD
Nonstop3h 22mUnited Airlines
Deal found 4/1$208
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/226:04 amMDW - RSW
1 stop4h 36mDelta
Tue 4/295:40 amRSW - MDW
1 stop7h 23mDelta
Deal found 4/1$217
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/37:05 amORD - RSW
1 stop6h 08mDelta
Wed 5/75:30 amRSW - ORD
1 stop5h 33mDelta
Deal found 4/1$227
This Frontier deal was found by Cheapflights users on 3/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/912:15 pmMDW - RSW
1 stop8h 08mFrontier
Mon 5/1210:11 amRSW - MDW
1 stop8h 17mFrontier
Deal found 3/31$228
This JetBlue deal was found by Cheapflights users on 4/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/18:40 amORD - RSW
1 stop10h 06mJetBlue
Thu 11/66:00 amRSW - ORD
1 stop10h 08mJetBlue
Deal found 4/1$275
This Sun Country Air deal was found by Cheapflights users on 4/1. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/317:51 pmORD - RSW
1 stop16h 21mSun Country Air
Wed 11/54:20 pmRSW - ORD
1 stop27h 00mSun Country Air
Deal found 4/1$285

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 April 2, 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

Thu 4/10

8:50 pm-12:59 am

Nonstop3h 09m

Fort Myers SW Florida Intl

Wed 4/16

8:52 am-10:59 am

Nonstop3h 07m

$139

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 4/13

8:50 pm-12:59 am

Nonstop3h 09m

Fort Myers SW Florida Intl

Sat 4/19

6:00 am-8:21 am

Nonstop3h 21m

$142

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 4/8

2:45 pm-6:47 pm

Nonstop3h 02m

Fort Myers SW Florida Intl

Fri 4/11

8:52 am-10:59 am

Nonstop3h 07m

$157

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 5/10

6:45 pm-10:52 pm

Nonstop3h 07m

Fort Myers SW Florida Intl

Sat 5/17

5:40 pm-7:54 pm

Nonstop3h 14m

$177

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 5/17

6:15 pm-10:05 pm

Nonstop2h 50m

Fort Myers SW Florida Intl

Sat 5/24

5:55 am-7:50 am

Nonstop2h 55m

$187

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 5/25

10:52 am-2:57 pm

Nonstop3h 05m

Fort Myers SW Florida Intl

Tue 6/3

4:33 pm-6:55 pm

Nonstop3h 22m

$208

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 4/22

6:04 am-11:40 am

1 stop4h 36m

Fort Myers SW Florida Intl

Tue 4/29

5:40 am-12:03 pm

1 stop7h 23m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 5/3

7:05 am-2:13 pm

1 stop6h 08m

Fort Myers SW Florida Intl

Wed 5/7

5:30 am-10:03 am

1 stop5h 33m

$227

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Fri 5/9

12:15 pm-9:23 pm

1 stop8h 08m

Fort Myers SW Florida Intl

Mon 5/12

10:11 am-5:28 pm

1 stop8h 17m

$228

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 6/8

6:30 am-9:12 pm

1 stop13h 42m

Fort Myers SW Florida Intl

Fri 6/13

11:43 am-5:15 pm

1 stop6h 32m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 24 results
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2
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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 March 28, 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 April 2, 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. Friday evenings 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 April 2, 2025.

The most flights from CHI to FM9 are scheduled on a Monday (31 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (8 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 April 2, 2025.
Read reviews from past customers who have flown Southwest, Delta and Avelo 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
4,272 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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.
Delta
8.0
Very good
7,898 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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
8,615 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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.
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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.

  • 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 $77. Frontier flights start at $82 while deals on American Airlines start at $89 one-way.

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

    Consider Air New Zealand (92%), Qatar Airways (92%) or Air Canada (91%) 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 $716 for a flight from Chicago to Fort Myers Beach. The cheapest flight overall is $54 while the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl) is currently priced at $89.

  • 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 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 April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$126FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$74Average$198FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$74Average$214FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$95Average$390FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$134Average$348FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$165Average$348FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$395FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$238Average$448FlexibilityNo cancel feeOn-time63%

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