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$80+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Fort Myers Beach are usually found in August or September, booked 46 days in advance, depart on a Wednesday or Tuesday and return on a Friday

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 November 5, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$153
(Kiwi.com)

One-way from

$80
(Southwest)

Popular in

March

Cheapest in

August

Average price

$335
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. 16% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 5, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/214:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Sat 12/276:15 amRSW - ORD
Nonstop3h 09mSpirit Airlines
Deal found 11/4$155
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/164:22 pmORD - RSW
2 stops24h 23mMultiple Airlines
Tue 12/239:55 pmRSW - ORD
Nonstop3h 01mMultiple Airlines
Deal found 11/5$156
This United Airlines deal was found by Cheapflights users on 11/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:25 amORD - RSW
Nonstop3h 01mUnited Airlines
Wed 12/109:20 amRSW - ORD
Nonstop3h 12mUnited Airlines
Deal found 11/3$157
This American Airlines deal was found by Cheapflights users on 11/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/97:15 pmORD - RSW
Nonstop3h 01mAmerican Airlines
Fri 12/126:20 pmRSW - ORD
Nonstop3h 24mAmerican Airlines
Deal found 11/4$158
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/158:15 amORD - RSW
Nonstop3h 05mSpirit Airlines
Fri 12/269:55 pmRSW - ORD
Nonstop3h 01mSpirit Airlines
Deal found 11/5$159
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:25 pmMDW - RSW
Nonstop2h 45mSouthwest
Thu 12/116:30 amRSW - MDW
Nonstop2h 55mSouthwest
Deal found 11/2$159
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Wed 12/312:29 pmORD - RSW
Nonstop2h 48mMultiple Airlines
Sun 12/712:32 pmRSW - ORD
1 stop26h 31mMultiple Airlines
Deal found 11/3$160
This Priceline deal was found by Cheapflights users on 11/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/178:26 amORD - RSW
1 stop11h 07mMultiple Airlines
Thu 11/201:38 pmRSW - ORD
Nonstop3h 08mMultiple Airlines
Deal found 11/4$161
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Thu 12/411:44 amORD - RSW
2 stops22h 53mMultiple Airlines
Thu 12/111:15 pmRSW - ORD
Nonstop3h 08mMultiple Airlines
Deal found 11/4$163
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Thu 12/118:15 amORD - RSW
Nonstop3h 05mMultiple Airlines
Fri 12/127:14 pmRSW - ORD
2 stops19h 02mMultiple Airlines
Deal found 11/4$164
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/184:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Mon 12/229:55 pmRSW - ORD
Nonstop3h 01mSpirit Airlines
Deal found 11/5$165
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Wed 12/312:29 pmORD - RSW
Nonstop2h 48mSpirit Airlines
Mon 12/81:15 pmRSW - ORD
Nonstop3h 08mSpirit Airlines
Deal found 11/4$166

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 November 5, 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 1/21

12:00 pm-8:02 pm

1 stop7h 02m

Fort Myers SW Florida Intl

Wed 1/28

9:20 am-11:35 am

Nonstop3h 15m

$208

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 12/6

11:25 am-10:17 pm

1 stop9h 52m

Fort Myers SW Florida Intl

Fri 12/12

3:10 pm-9:52 pm

1 stop7h 42m

$211

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 12/7

6:45 am-1:05 pm

1 stop5h 20m

Fort Myers SW Florida Intl

Mon 12/15

8:00 am-12:01 pm

1 stop5h 01m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 12/2

4:20 pm-12:37 am

1 stop7h 17m

Fort Myers SW Florida Intl

Tue 12/9

5:38 pm-10:43 pm

1 stop6h 05m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 12/12

8:55 am-4:51 pm

1 stop6h 56m

Fort Myers SW Florida Intl

Mon 12/15

7:49 pm-12:01 am

1 stop5h 12m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 1/23

5:33 am-11:57 am

1 stop5h 24m

Fort Myers SW Florida Intl

Mon 1/26

6:02 pm-11:57 pm

1 stop6h 55m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 1/31

5:59 pm-12:32 am

1 stop5h 33m

Fort Myers SW Florida Intl

Tue 2/3

8:10 am-1:39 pm

1 stop6h 29m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 12/10

10:49 am-4:32 pm

1 stop4h 43m

Fort Myers SW Florida Intl

Mon 12/15

5:35 am-9:54 am

1 stop5h 19m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 12/9

12:50 pm-6:44 pm

1 stop4h 54m

Fort Myers SW Florida Intl

Sat 12/13

5:38 pm-11:47 pm

1 stop7h 09m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Fri 12/12

1:14 pm-9:45 pm

1 stop7h 31m

Fort Myers SW Florida Intl

Tue 12/16

5:35 am-9:54 am

1 stop5h 19m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

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 October 31, 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, March is the cheapest month in which you can book a flight from Chicago to Fort Myers Beach (average of $44). Flying from Chicago to Fort Myers Beach in November is currently the most expensive (average of $120). 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 November 5, 2025.

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 30% 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 December 16, 2024.

Travelers seeking maximum savings on their Chicago to Fort Myers Beach flight should consider departing on Friday evenings when fares are most often at their lowest. Wednesday 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 November 5, 2025.

The most flights from CHI to FM9 are scheduled on a Monday (22 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 November 5, 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
4,240 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

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
9,002 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

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.
American Airlines
7.2
Good
11,042 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

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.
Spirit Airlines
6.3
Okay
8,115 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

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.
Frontier
5.8
Fair
3,116 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

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.

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

    A quick flight from Chicago to Fort Myers Beach can take about 5h 20m. United Airlines provides one of the quickest options available for as low as $217. The distance between Chicago and Fort Myers Beach is about 1122 mi. This flight may include one or multiple stops.

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

    Consider Spirit Airlines (94%), Air New Zealand (93%) or Air Canada (92%) 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 $617 for a flight from Chicago to Fort Myers Beach. The cheapest flight overall is $75 while the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl) is currently priced at $85.

  • 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, March is the cheapest month in which you can book a flight from Chicago to Fort Myers Beach (average of $44). Flying from Chicago to Fort Myers Beach in November is currently the most expensive (average of $120). 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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See prices for flight routes from nearby airports that may be better suited for you.
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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 November 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$124FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$74Average$175FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$85Average$302FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$95Average$217FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$156Average$297FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$166Average$370FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$172Average$415FlexibilityNo cancel feeOn-time63%
DeltaCheapest$178Average$354FlexibilityNo cancel feeOn-timeN/A

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