HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Fort Myers Beach

$74+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Jan 23 — Jan 301
Fri 1/23
Fri 1/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Fort Myers Beach with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Fort Myers Beach are usually found in August or September, booked 55 days in advance, depart on a Wednesday or Tuesday 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 December 24, 2025.

This Expedia deal was found by Cheapflights users on 12/22. 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.
Wed 12/316:05 amORD - RSW
1 stop11h 13mFrontier
Sat 2/216:49 pmRSW - ORD
Nonstop3h 32mFrontier
Deal found 12/22$120
This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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.
Wed 12/314:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Sat 2/216:00 amRSW - ORD
Nonstop3h 13mSpirit Airlines
Deal found 12/22$124
This Super.com deal was found by Cheapflights users on 12/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Fri 2/206:00 amRSW - ORD
Nonstop3h 13mSpirit Airlines
Deal found 12/22$132
This Super.com deal was found by Cheapflights users on 12/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Sat 2/146:00 amRSW - ORD
Nonstop3h 13mSpirit Airlines
Deal found 12/22$150
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/316:05 amORD - RSW
1 stop11h 13mMultiple Airlines
Fri 2/206:00 amRSW - ORD
Nonstop3h 13mMultiple Airlines
Deal found 12/22$152
This American Airlines deal was found by Cheapflights users on 12/23. 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.
Wed 12/317:49 pmORD - RSW
Nonstop3h 08mAmerican Airlines
Sat 2/148:00 amRSW - ORD
Nonstop3h 17mAmerican Airlines
Deal found 12/23$157
This American Airlines deal was found by Cheapflights users on 12/22. 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.
Wed 12/317:49 pmORD - RSW
Nonstop3h 08mAmerican Airlines
Thu 1/226:28 amRSW - ORD
Nonstop3h 16mAmerican Airlines
Deal found 12/22$168
This Super.com deal was found by Cheapflights users on 12/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Fri 1/97:45 pmRSW - ORD
Nonstop3h 19mSpirit Airlines
Deal found 12/22$169
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/314:55 pmORD - RSW
Nonstop3h 05mMultiple Airlines
Fri 1/97:25 pmRSW - ORD
1 stop28h 11mMultiple Airlines
Deal found 12/22$171
This Expedia deal was found by Cheapflights users on 12/22. 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.
Wed 12/316:05 amORD - RSW
1 stop11h 13mFrontier
Sat 2/141:55 pmRSW - ORD
1 stop9h 44mFrontier
Deal found 12/22$182
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/316:05 amORD - RSW
1 stop11h 13mFrontier
Fri 2/202:41 pmRSW - ORD
1 stop8h 58mFrontier
Deal found 12/22$197
This Southwest deal was found by Cheapflights users on 12/24. 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 12/314:35 pmMDW - RSW
1 stop4h 30mSouthwest
Thu 1/111:00 amRSW - MDW
1 stop9h 15mSouthwest
Deal found 12/24$262

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 December 24, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$95
(CheapOair)

One-way from

$74
(Super.com)

Popular in

December

Cheapest in

August

Average price

$388
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. 15% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 24, 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

9:40 am-6:30 pm

1 stop7h 50m

Fort Myers SW Florida Intl

Fri 2/6

12:10 pm-7:45 pm

1 stop8h 35m

$181

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 2/7

7:45 am-7:03 pm

1 stop10h 18m

Fort Myers SW Florida Intl

Tue 2/10

12:10 pm-7:31 pm

1 stop8h 21m

$181

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Mon 3/9

12:41 pm-11:53 pm

1 stop10h 12m

Fort Myers SW Florida Intl

Fri 3/13

10:30 am-5:24 pm

1 stop7h 54m

$181

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sun 1/25

7:30 am-1:10 pm

1 stop4h 40m

Fort Myers SW Florida Intl

Sat 1/31

6:15 am-8:15 am

Nonstop3h 00m

$207

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Mon 2/2

5:45 pm-9:30 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Thu 2/5

5:00 am-7:00 am

Nonstop3h 00m

$208

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 2/6

5:59 pm-12:32 am

1 stop5h 33m

Fort Myers SW Florida Intl

Wed 2/11

6:02 pm-11:56 pm

1 stop6h 54m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 1/30

5:59 pm-12:32 am

1 stop5h 33m

Fort Myers SW Florida Intl

Sun 2/1

5:35 am-10:05 am

1 stop5h 30m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 1/22

9:55 am-6:42 pm

1 stop7h 47m

Fort Myers SW Florida Intl

Sun 1/25

7:49 pm-11:56 pm

1 stop5h 07m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 2/3

9:40 am-6:30 pm

1 stop7h 50m

Fort Myers SW Florida Intl

Sat 2/7

12:10 pm-7:45 pm

1 stop8h 35m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 1/23

5:59 pm-12:32 am

1 stop5h 33m

Fort Myers SW Florida Intl

Mon 1/26

7:49 pm-11:56 pm

1 stop5h 07m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/23

Showing 1-10 of 48 results
1
2
3
...
5

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 December 19, 2025.

Booking 55 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 $42). 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 December 24, 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 at noon 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 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. 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 December 24, 2025.

The most flights from CHI to FM9 are scheduled on a Monday (28 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (19 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 December 24, 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
4,257 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

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
4,257 reviews
Southwest
8.0
Very good
4,257 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

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
9,116 reviews
Southwest
8.0
Very good
4,257 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

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
11,056 reviews
Southwest
8.0
Very good
4,257 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

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
8,203 reviews
Southwest
8.0
Very good
4,257 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

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
3,068 reviews
Southwest
8.0
Very good
4,257 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

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 4h 40m. JetBlue provides one of the quickest options available for as low as $207. 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 $29. Spirit Airlines flights start at $40 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 (85%), Air Canada (81%) or Spirit Airlines (81%) 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 $577 for a flight from Chicago to Fort Myers Beach. The cheapest flight overall is $56 while the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl) is currently priced at $59.

  • 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 $42). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Fort Myers Beach

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Myers flights
Midway to Orlando flights
O'Hare Intl to West Palm Beach flights
Midway to Fort Lauderdale flights
Midway to Miami flights
O'Hare Intl to Sarasota flights
Midway to Tampa flights
O'Hare Intl to Key West flights
St. Louis to Orlando flights
O'Hare Intl to Jacksonville flights
Midway to Fort Myers flights
St. Louis to Miami flights
O'Hare Intl to Pensacola flights
St. Louis to Fort Lauderdale flights
Midway to West Palm Beach flights
O'Hare Intl to Panama City flights
Midway to Key West flights
St. Louis to Tampa flights
St. Louis to Fort Myers flights
Midway to Jacksonville flights
Midway to Pensacola flights
Midway to Sarasota flights
St. Louis to Key West flights
St. Louis to Jacksonville flights
Moline to Orlando flights
Rockford to St Petersburg flights
Peoria to Orlando flights
Moline to Tampa flights
Peoria to Miami flights
Rockford to Orlando Sanford Intl flights
Midway to Panama City flights
Rockford to Punta Gorda flights
St. Louis to Sarasota flights
Moline to Fort Myers flights
Moline to Miami flights
Peoria to Fort Myers flights
O'Hare Intl to Valparaiso flights
Peoria to Fort Lauderdale flights
St. Louis to Pensacola flights
Midway to Punta Gorda flights
O'Hare Intl to Daytona Beach flights
Moline to Pensacola flights
St. Louis to West Palm Beach flights
Moline to Fort Lauderdale flights
Bloomington to Orlando flights
O'Hare Intl to Melbourne flights

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 December 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$127FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$75Average$198FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$79Average$295FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$143Average$217FlexibilityNo cancel feeOn-time62%
DeltaCheapest$149Average$426FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$156Average$293FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$160Average$363FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$171Average$401FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2025 Cheapflights