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$74+ Cheap flights from Chicago (CHI) to Fort Myers (RSW)

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 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Find cheap flights from Chicago to Fort Myers 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

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3. Compare prices and book

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Cheapflights Tip: The best prices from Chicago to Fort Myers SW Florida Intl 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

Cheapest flights from Chicago to Fort Myers
Explore the most affordable flight options available from Chicago to Fort Myers. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 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 12/22. 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 12/21. 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 1/105:42 pmRSW - ORD
Nonstop3h 18mFrontier
Deal found 12/21$172
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/312:15 pmORD - RSW
1 stop19h 03mMultiple Airlines
Tue 1/137:31 amRSW - ORD
Nonstop3h 12mMultiple Airlines
Deal found 12/21$179
This American Airlines deal was found by Cheapflights users on 12/21. 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 1/106:04 amRSW - ORD
Nonstop3h 16mAmerican Airlines
Deal found 12/21$185
This Southwest deal was found by Cheapflights users on 12/21. 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 12/3111:25 amMDW - RSW
1 stop9h 20mSouthwest
Thu 1/111:00 amRSW - MDW
1 stop9h 15mSouthwest
Deal found 12/21$308

Find flight deals from Chicago to Fort Myers

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Fort Myers (RSW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 23, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$96
(Frontier)

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 SW Florida Intl
Search Deals
One-way flight from Chicago (CHI) to Fort Myers SW Florida Intl
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 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 23, 2025.
Use the filters below to find and compare flights from Chicago to Fort Myers that are best for you.

Fly from

Chicago

Fly to

Fort Myers

Route

Depart

Return

Price

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 1/20

9:40 am-6:30 pm

1 stop7h 50m

Fort Myers SW Florida Intl

Tue 1/27

10:10 am-7:36 pm

1 stop10h 26m

$181

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 3/18

10:56 am-7:03 pm

1 stop7h 07m

Fort Myers SW Florida Intl

Thu 3/19

7:19 am-5:24 pm

1 stop11h 05m

$197

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sun 1/11

6:00 am-9:55 am

Nonstop2h 55m

Fort Myers SW Florida Intl

Sat 1/17

10:00 am-6:40 pm

2 stops9h 40m

$200

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 1/10

9:15 am-1:29 pm

Nonstop3h 14m

Fort Myers SW Florida Intl

Sat 1/17

4:27 pm-6:50 pm

Nonstop3h 23m

$207

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 2/4

9:50 am-5:20 pm

1 stop6h 30m

Fort Myers SW Florida Intl

Sat 2/7

6:15 am-8:15 am

Nonstop3h 00m

$207

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 1/21

5:59 pm-12:32 am

1 stop5h 33m

Fort Myers SW Florida Intl

Thu 1/29

7:49 pm-11:56 pm

1 stop5h 07m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 1/25

5:30 am-11:55 am

1 stop5h 25m

Fort Myers SW Florida Intl

Wed 1/28

3:05 pm-7:21 pm

1 stop5h 16m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 1/25

10:35 am-5:51 pm

1 stop6h 16m

Fort Myers SW Florida Intl

Sun 2/1

6:00 am-1:13 pm

1 stop8h 13m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 1/6

9:35 am-6:30 pm

1 stop7h 55m

Fort Myers SW Florida Intl

Tue 1/13

12:10 pm-7:36 pm

1 stop8h 26m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 1/24

5:30 am-11:29 am

1 stop4h 59m

Fort Myers SW Florida Intl

Sat 1/24

6:02 pm-11:56 pm

1 stop6h 54m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 45 results
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Compare providers for flights from Chicago to Fort Myers

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Fort Myers in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Fort Myers flights, users find the pricing of Justfly.com to be most consistent on Cheapflights vs. Justfly.com Users can find the same prices on Chicago-Fort Myers flight deals on Cheapflights vs. Justfly.com >95% of the time. Price accuracy is based on data collected from Chicago-Fort Myers flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Fort Myers flights, Cheapflights users trust Justfly.com the most. Justfly.com has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Fort Myers flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Fort Myers

Have a flexible travel schedule? Discover the best time to fly to Fort Myers 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

How far ahead should I book a flight from Chicago to Fort Myers?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Fort Myers. Price data was last updated on December 19, 2025.

The best time to book flights from Chicago to Fort Myers is 55 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Fort Myers?

Currently, March is the cheapest month in which you can book a flight from Chicago to Fort Myers (average of $42). Flying from Chicago to Fort Myers 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 RSW?

Find hourly flight availability from Chicago to Fort Myers. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Fort Myers in the evening. If you’re flexible enough to do this you can expect to save up to 28% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Chicago to Fort Myers?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Fort Myers. Price data was last updated on December 20, 2025.

Travelers seeking maximum savings on their Chicago to Fort Myers flight should consider departing on Wednesday mornings when fares are most often at their lowest. Sunday 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

Explore weekly flight availability from Chicago to Fort Myers. 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 23, 2025.

The most flights from CHI to RSW are scheduled on a Sunday (32 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (13 on average).

How much does it cost to fly round-trip from Chicago to Fort Myers?

How often are flights from Chicago to Fort Myers delayed?

About 15% of weekly flights between Chicago and Fort Myers have experienced delays in the past year, with the average delay time being 149 minutes.

What is the most punctual flight time for Chicago to Fort Myers flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Fort Myers flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 12% of flights being delayed.

The best insider tips for Chicago to Fort Myers flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Fort Myers trip
Airlines
Spirit Airlines

Spirit's Big Front Seats offer 11 extra inches of legroom, ideal for comfort on short flights.


Use Spirit's self-service bag drop for a quicker airport experience; print your boarding pass in advance.

Read more about Spirit AirlinesBy Daniel Scheffler
Southwest

Southwest offers free snacks and non-alcoholic drinks, enhancing the short flight experience.


Enjoy free messaging and in-flight entertainment on Southwest, perfect for staying connected.

Read more about SouthwestBy Marisa Garcia
Airports
ORD

Take the “L” train to ORD to avoid Chicago traffic; it’s a reliable public transport option from the city center.

Read more about ORDBy Ramsey Qubein
MDW

Order food via the airport’s mobile system directly to your gate to save time and keep your place in line.

Read more about MDWBy Ramsey Qubein
RSW

Use LeeTran Route 50 for public transport from RSW; it runs hourly from 7:24 am to 8:50 pm.

Read more about RSWBy Matt Meltzer
Our travel experts
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Matt Meltzer

Matt Meltzer

Expert on RSW

Matt Meltzer

Matt Meltzer

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more

Reviews of airlines servicing Fort Myers

Get insights into the airlines that provide service to Fort Myers. 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. Reviews last updated December 23, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from Chicago to Fort Myers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

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
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

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
9,105 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

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
11,054 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

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
8,196 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

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
3,075 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

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. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Fort Myers from Chicago?

    Located just 10.0 mi from the city center, Fort Myers SW Florida Intl is the airport most travelers will use when flying to Fort Myers from Chicago. Booking flights from Chicago to SW Florida Intl (RSW) should be relatively easy as there are 25 daily inbound flights from Chicago from 7 different airlines.

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

    Airlines like JetBlue, Southwest, and United Airlines fly from Chicago to Fort Myers in about 2h 55m. The time it takes to get you to your destination can typically vary by up to 4h 55m. The distance between Chicago and Fort Myers is about 1106 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Fort Myers round-trip?

    Flying on Frontier is currently your cheapest option to Fort Myers, with prices starting at $52. Additional round-trip tickets that might be worth considering are offered by Spirit Airlines and JetBlue, with the lowest prices starting at $76 and $95, respectively. These flights start at 80% lower than the current average price 3 months from now.

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

    The cheapest airlines for a one-way flight from Chicago to Fort Myers are Frontier ($29), Spirit Airlines ($40), and American Airlines ($78).

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

    No one likes to see their flight delayed. When booking a flight from Chicago to Fort Myers consider choosing Air New Zealand (85%), Air Canada (81%) or Spirit Airlines (81%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Fort Myers?

    While on average a flight from Chicago to Fort Myers is generally $577, our data shows the cheapest flight currently is $56. When looking at the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl), you can expect to pay $59 for that flight.

  • Can I find deals for flights from Chicago to Fort Myers that include hotel bookings?

    Yes. In addition to deals on Chicago to Fort Myers flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Fort Myers?

    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.

  • Can I find deals for business class flights from Chicago to Fort Myers?

    Yes. Cheapflights offers flight deals from Chicago to Fort Myers 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?

    Currently, March is the cheapest month in which you can book a flight from Chicago to Fort Myers (average of $42). Flying from Chicago to Fort Myers 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

Traveling to a place near Fort Myers?

Book flights to Fort Myers if you plan to visit one of these locations
Sanibel
North Fort Myers
Estero
Lehigh Acres

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Alternative routes for Chicago to Fort Myers

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Chicago to Fort Myers

Discover the top 7 airlines that operate flights from Chicago to Fort Myers. 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 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$55Average$138FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$79Average$220FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$143Average$217FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$156Average$254FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$160Average$326FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$171Average$400FlexibilityNo cancel feeOn-time63%
DeltaCheapest$178Average$466FlexibilityNo cancel feeOn-timeN/A

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