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$64+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Fort Myers SW Florida Intl are usually found in August or July, booked 36 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap 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 September 11, 2025.

Round-trip from

$109
(Cheapflightsfares)

One-way from

$64
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$255
From Chicago (CHI) to Fort Myers SW Florida Intl
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One-way flight from Chicago (CHI) to Fort Myers SW Florida Intl
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Highest demand for flights based on searches. 12% potential increase in price ($39 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 September 2025
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Find 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 September 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 10/124:51 pmORD - RSW
Nonstop2h 50mSpirit Airlines
Thu 10/166:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Deal found 9/9$109
This Priceline deal was found by Cheapflights users on 9/9. 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.
Sun 10/54:51 pmORD - RSW
Nonstop2h 50mSpirit Airlines
Fri 10/176:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Deal found 9/9$110
This Priceline deal was found by Cheapflights users on 9/9. 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.
Fri 11/77:00 amORD - RSW
Nonstop2h 51mSpirit Airlines
Fri 11/1411:56 amRSW - ORD
Nonstop3h 10mSpirit Airlines
Deal found 9/9$115
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/25:23 pmORD - RSW
Nonstop2h 53mSpirit Airlines
Fri 10/37:00 amRSW - ORD
Nonstop3h 13mSpirit Airlines
Deal found 9/9$116
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Thu 10/25:23 pmORD - RSW
Nonstop2h 53mSpirit Airlines
Mon 10/66:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Deal found 9/10$117
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Fri 10/35:23 pmORD - RSW
Nonstop2h 53mSpirit Airlines
Mon 10/66:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Deal found 9/11$119
This CheapOair deal was found by Cheapflights users on 9/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:16 pmORD - RSW
Nonstop2h 53mSpirit Airlines
Fri 10/106:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Deal found 9/11$120
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sun 10/124:51 pmORD - RSW
Nonstop2h 50mSpirit Airlines
Fri 10/176:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Deal found 9/9$121
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 12/117:00 amORD - RSW
Nonstop2h 51mSpirit Airlines
Sun 12/1411:56 amRSW - ORD
Nonstop3h 10mSpirit Airlines
Deal found 9/10$123
This Priceline deal was found by Cheapflights users on 9/11. 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 9/295:23 pmORD - RSW
Nonstop2h 53mSpirit Airlines
Fri 10/37:00 amRSW - ORD
Nonstop3h 13mSpirit Airlines
Deal found 9/11$124
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 9/295:23 pmORD - RSW
Nonstop2h 53mSpirit Airlines
Thu 10/27:00 amRSW - ORD
Nonstop3h 13mSpirit Airlines
Deal found 9/10$125
This Southwest deal was found by Cheapflights users on 9/11. 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.
Tue 10/286:50 pmMDW - RSW
Nonstop2h 40mSouthwest
Tue 11/46:30 amRSW - MDW
Nonstop2h 55mSouthwest
Deal found 9/11$133

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 September 11, 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

Wed 10/29

7:25 am-11:26 am

Nonstop3h 01m

Fort Myers SW Florida Intl

Fri 11/7

4:38 pm-6:50 pm

Nonstop3h 12m

$146

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 10/29

7:25 am-11:26 am

Nonstop3h 01m

Fort Myers SW Florida Intl

Thu 10/30

2:45 pm-4:59 pm

Nonstop3h 14m

$146

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 1/13

5:45 pm-9:30 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Fri 1/23

7:25 am-9:20 am

Nonstop2h 55m

$165

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 10/18

5:30 pm-9:10 pm

Nonstop2h 40m

Fort Myers SW Florida Intl

Wed 10/22

6:05 am-7:55 am

Nonstop2h 50m

$175

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 12/10

10:35 am-8:14 pm

1 stop8h 39m

Fort Myers SW Florida Intl

Sat 12/13

4:29 pm-6:41 pm

Nonstop3h 12m

$177

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 11/12

11:00 am-8:03 pm

1 stop8h 03m

Fort Myers SW Florida Intl

Tue 11/18

9:10 am-11:22 am

Nonstop3h 12m

$177

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 10/15

7:15 am-11:18 am

Nonstop3h 03m

Fort Myers SW Florida Intl

Wed 10/22

7:00 am-2:55 pm

1 stop8h 55m

$177

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 10/15

6:50 pm-10:30 pm

Nonstop2h 40m

Fort Myers SW Florida Intl

Wed 10/22

6:05 am-7:55 am

Nonstop2h 50m

$186

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 10/8

5:45 am-12:00 pm

1 stop5h 15m

Fort Myers SW Florida Intl

Sat 10/11

7:10 am-9:00 am

Nonstop2h 50m

$187

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 10/15

7:15 am-11:18 am

Nonstop3h 03m

Fort Myers SW Florida Intl

Tue 10/21

12:25 pm-2:40 pm

Nonstop3h 15m

$190

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 44 results
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The best insider tips for Chicago to Fort Myers flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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

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 August 29, 2025.

The best time to book flights from Chicago to Fort Myers is 35 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, January is the cheapest month in which you can book a flight from Chicago to Fort Myers (average of $205). Flying from Chicago to Fort Myers in June is currently the most expensive (average of $290). 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 September 11, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Fort Myers in the afternoon. If you’re flexible enough to do this you can expect to save up to 14% 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 September 7, 2025.

Travelers seeking maximum savings on their Chicago to Fort Myers flight should consider departing on Sunday afternoons 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 September 11, 2025.

The most flights from CHI to RSW are scheduled on a Thursday (16 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

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

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 September 11, 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
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

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
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

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
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

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. 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 13 daily inbound flights from Chicago from 6 different airlines.

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

    Airlines like United Airlines and Southwest fly from Chicago to Fort Myers in about 2h 45m. The time it takes to get you to your destination is usually consistent. The distance between Chicago and Fort Myers is about 1106 mi. Generally, flights for this route are nonstop.

  • 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 $54. Additional round-trip tickets that might be worth considering are offered by Spirit Airlines and American Airlines, with the lowest prices starting at $83 and $160, respectively. These flights start at 81% lower than the current average price 3 months from now.

  • 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 (88%), Air Canada (80%) or Spirit Airlines (79%) 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 $468, our data shows the cheapest flight currently is $48. When looking at the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl), you can expect to pay $107 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, January is the cheapest month in which you can book a flight from Chicago to Fort Myers (average of $205). Flying from Chicago to Fort Myers in June is currently the most expensive (average of $290). 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 6 airlines flying from Chicago to Fort Myers

Discover the top 6 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$54Average$135FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$291FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$160Average$299FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$174Average$467FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$177Average$365FlexibilityNo cancel feeOn-time69%
DeltaCheapest$178Average$372FlexibilityNo cancel feeOn-timeN/A

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