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$67+ 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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 January, booked 46 days in advance, depart on a Tuesday or Wednesday 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 July 30, 2025.

Round-trip from

$91
(Kiwi.com)

One-way from

$67
(Booking.com)

Popular in

March

Cheapest in

August

Average price

$256
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 ($40 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 July 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 July 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Fri 9/125:31 pmORD - RSW
Nonstop2h 53mSpirit Airlines
Thu 9/187:00 amRSW - ORD
Nonstop3h 13mSpirit Airlines
Deal found 7/29$91
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/202:44 pmORD - RSW
Nonstop3h 06mAmerican Airlines
Wed 9/248:00 amRSW - ORD
Nonstop3h 09mAmerican Airlines
Deal found 7/30$157
This Southwest deal was found by Cheapflights users on 7/29. 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 9/26:20 pmMDW - RSW
Nonstop2h 45mSouthwest
Wed 9/109:15 amRSW - MDW
Nonstop2h 50mSouthwest
Deal found 7/29$157
This Booking.com deal was found by Cheapflights users on 7/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3110:43 amORD - RSW
1 stop9h 47mMultiple Airlines
Wed 9/37:00 amRSW - ORD
Nonstop3h 07mMultiple Airlines
Deal found 7/28$160
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/216:00 amMDW - RSW
1 stop4h 50mDelta
Mon 10/276:41 pmRSW - MDW
1 stop4h 33mDelta
Deal found 7/30$217
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/316:20 amMDW - RSW
1 stop11h 00mFrontier
Sun 8/37:16 pmRSW - MDW
1 stop5h 01mFrontier
Deal found 7/30$238

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 July 30, 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

Fri 9/12

5:31 pm-9:24 pm

Nonstop2h 53m

Fort Myers SW Florida Intl

Thu 9/18

7:00 am-9:13 am

Nonstop3h 13m

$91

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 9/20

2:44 pm-6:50 pm

Nonstop3h 06m

Fort Myers SW Florida Intl

Wed 9/24

8:00 am-10:09 am

Nonstop3h 09m

$157

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 9/2

6:20 pm-10:05 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Wed 9/10

9:15 am-11:05 am

Nonstop2h 50m

$157

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 8/31

10:43 am-9:30 pm

1 stop9h 47m

Fort Myers SW Florida Intl

Wed 9/3

7:00 am-9:07 am

Nonstop3h 07m

$160

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 8/28

7:16 am-11:19 am

Nonstop3h 03m

Fort Myers SW Florida Intl

Thu 8/28

4:39 pm-6:55 pm

Nonstop3h 16m

$171

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 10/21

6:00 am-11:50 am

1 stop4h 50m

Fort Myers SW Florida Intl

Mon 10/27

6:41 pm-10:14 pm

1 stop4h 33m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sun 8/31

11:03 am-6:24 pm

1 stop6h 21m

Fort Myers SW Florida Intl

Sun 9/7

7:24 pm-11:20 pm

1 stop4h 56m

$239

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 8/9

4:34 pm-8:29 pm

Nonstop2h 55m

$67

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 9/6

7:16 am-11:19 am

Nonstop3h 03m

$79

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 10/4

5:30 pm-9:10 pm

Nonstop2h 40m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 18 results
1
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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
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
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 July 25, 2025.

The best time to book flights from Chicago to Fort Myers is 46 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 July 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Fort Myers in the morning. 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 July 27, 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. 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

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 July 30, 2025.

The most flights from CHI to RSW are scheduled on a Wednesday (17 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 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 July 30, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

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 9 daily inbound flights from Chicago from 7 different airlines.

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

    Flying on Spirit Airlines is currently your cheapest option to Fort Myers, with prices starting at $91. Additional round-trip tickets that might be worth considering are offered by American Airlines and Southwest, with the lowest prices starting at $157 and $157, respectively. These flights start at 68% 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 Spirit Airlines ($67), United Airlines ($79), and Southwest ($79).

  • 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%), Qatar Airways (80%) or Alaska Airlines (80%) 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 $348, our data shows the cheapest flight currently is $45. When looking at the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl), you can expect to pay $57 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 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$54Average$135FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$69Average$382FlexibilityNo cancel feeOn-time83%
Spirit AirlinesCheapest$83Average$293FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$162Average$303FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$173Average$444FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$176Average$360FlexibilityNo cancel feeOn-time69%
DeltaCheapest$216Average$370FlexibilityNo cancel feeOn-timeN/A

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