How many flights depart from Chicago to Fort Myers on average per week?

105 flights are operational weekly from Chicago to Fort Myers as of November 2025. The most popular departure day for this route is Tue, with 26% of flights per week taking off on this day.

How often are flights from Chicago to Fort Myers delayed?

Historically, on average around 14% of flights between Chicago and Fort Myers have experienced a delay on any given week. The average delay length over the past 12 months has been 148 minutes.

How many flights depart from Chicago to Fort Myers on average per day?

As of November 2025, 15 flights take off from Chicago and land in Fort Myers each day. The most common flight departure time for this route is 7:00AM, with 52% of daily flights taking off at noon.

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

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

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

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

What airlines fly to Fort Myers?

United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Fort Myers from Chicago according to our data. United Airlines is the first choice among our users, with 32% of people opting to fly with this airline when traveling to Fort Myers. Keep in mind that there are 8 different airlines that fly to Fort Myers on a routine basis, so you have a few additional options to choose from.

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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 12% of their flights experiencing any sort of delay.

What is the cheapest airline that flies from Chicago to Fort Myers SW Florida Intl?

United Airlines, Southwest, and JetBlue are the most popular carriers operating from Chicago to Fort Myers SW Florida Intl

When did momondo last update prices for flights from Chicago to Fort Myers SW Florida Intl Airport?

Prices for flights from Chicago to Fort Myers SW Florida Intl Airport are refreshed on a daily basis.

How many operators does momondo search for flights from Chicago to Fort Myers SW Florida Intl Airport?

As of November 2025, there are 7 operators available to choose from for flights from Chicago to Fort Myers SW Florida Intl Airport.

How old do you have to be to fly from Chicago to Fort Myers SW Florida Intl Airport?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Fort Myers SW Florida Intl Airport.

What documentation or ID do you need to fly to Fort Myers SW Florida Intl Airport?

The required travel and health documents for your Fort Myers SW Florida Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Fort Myers SW Florida Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$58 Cheap Flights from Chicago to Fort Myers in 2025/26

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4:44 pm - 12:11 pmORD-RSW

18h 27m1 stop

7:20 pm - 9:39 pmRSW-ORD

3h 19mnonstop

$151Multiple Airlines

Find Deal

Fri, Jan 23 - Wed, Jan 28

8:15 am - 12:20 pmORD-RSW

3h 05mnonstop

9:55 pm - 11:56 pmRSW-ORD

3h 01mnonstop

$152Spirit Airlines

Find Deal

Sun, Dec 7 - Sat, Dec 27

6:14 pm - 10:45 amORD-RSW

15h 31m1 stop

7:22 am - 9:34 amRSW-ORD

3h 12mnonstop

$153Multiple Airlines

Find Deal

Thu, Jan 1 - Sat, Jan 31

9:00 pm - 11:46 amORD-RSW

13h 46m1 stop

7:22 am - 9:34 amRSW-ORD

3h 12mnonstop

$154Multiple Airlines

Find Deal

Sat, Jan 10 - Sat, Jan 17

6:10 am - 6:43 pmORD-RSW

11h 33m1 stop

5:42 pm - 8:00 pmRSW-ORD

3h 18mnonstop

$155Frontier

Find Deal

Sat, Jan 3 - Sat, Jan 10

7:00 am - 11:01 amORD-RSW

3h 01mnonstop

8:46 pm - 6:29 pmRSW-ORD

22h 43m2 stops

$156Multiple Airlines

Find Deal

Mon, Jan 19 - Sat, Feb 7

7:35 pm - 9:07 amORD-RSW

12h 32m1 stop

7:22 am - 9:34 amRSW-ORD

3h 12mnonstop

$157Multiple Airlines

Find Deal

Thu, Jan 15 - Tue, Jan 20

6:00 am - 9:55 amMDW-RSW

2h 55mnonstop

6:15 am - 8:15 amRSW-MDW

3h 00mnonstop

$163Southwest

Find Deal

Sun, Jan 11 - Sat, Jan 17

10:00 am - 4:10 pmMDW-RSW

5h 10m1 stop

6:15 am - 8:15 amRSW-MDW

3h 00mnonstop

$173Southwest

Find Deal

Wed, Jan 7 - Sat, Jan 10

6:00 am - 6:30 pmMDW-RSW

11h 30m1 stop

7:14 pm - 11:42 pmRSW-MDW

5h 28m1 stop

$182Frontier

Find Deal

Sat, Feb 21 - Mon, Mar 9

Southwest flights from Chicago to Fort Myers

Our best Southwest deals on Chicago to Fort Myers flight tickets

Southwest

Jan 11

MDW6:00 amChicago Midway

2h 55m

RSW9:55 amFort Myers SW Florida Intl

Jan 17

RSW6:15 amFort Myers SW Florida Intl

3h 00m

MDW8:15 amChicago Midway

$163

Find similar

Southwest

Jan 7

MDW10:00 amChicago Midway

5h 10m

1 stop

RSW4:10 pmFort Myers SW Florida Intl

Jan 10

RSW6:15 amFort Myers SW Florida Intl

3h 00m

MDW8:15 amChicago Midway

$173

Find similar

Southwest

Jan 7

MDW1:15 pmChicago Midway

6h 45m

1 stop

RSW9:00 pmFort Myers SW Florida Intl

Jan 11

RSW5:00 amFort Myers SW Florida Intl

3h 00m

MDW7:00 amChicago Midway

$179

Find similar

Spirit Airlines flights from Chicago to Fort Myers

Our best Spirit Airlines deals on Chicago to Fort Myers flight tickets

Spirit Airlines

Dec 7

ORD8:15 amChicago O'Hare Intl

3h 05m

RSW12:20 pmFort Myers SW Florida Intl

Dec 27

RSW9:55 pmFort Myers SW Florida Intl

3h 01m

ORD11:56 pmChicago O'Hare Intl

$152

Find similar

Spirit Airlines

Dec 5

ORD8:15 amChicago O'Hare Intl

3h 05m

RSW12:20 pmFort Myers SW Florida Intl

Dec 24

RSW9:55 pmFort Myers SW Florida Intl

3h 01m

ORD11:56 pmChicago O'Hare Intl

$159

Find similar

Spirit Airlines

Dec 18

ORD9:19 amChicago O'Hare Intl

3h 10m

RSW1:29 pmFort Myers SW Florida Intl

Dec 23

RSW6:15 amFort Myers SW Florida Intl

3h 09m

ORD8:24 amChicago O'Hare Intl

$160

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Fly from

Fly to

Route

Depart

Return

Price

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 1/23

4:44 pm-12:11 pm

1 stop18h 27m

Fort Myers SW Florida Intl

Wed 1/28

7:20 pm-9:39 pm

Nonstop3h 19m

$151

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 12/7

8:15 am-12:20 pm

Nonstop3h 05m

Fort Myers SW Florida Intl

Sat 12/27

9:55 pm-11:56 pm

Nonstop3h 01m

$152

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 1/1

6:14 pm-10:45 am

1 stop15h 31m

Fort Myers SW Florida Intl

Sat 1/31

7:22 am-9:34 am

Nonstop3h 12m

$153

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 1/10

9:00 pm-11:46 am

1 stop13h 46m

Fort Myers SW Florida Intl

Sat 1/17

7:22 am-9:34 am

Nonstop3h 12m

$154

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 1/3

6:10 am-6:43 pm

1 stop11h 33m

Fort Myers SW Florida Intl

Sat 1/10

5:42 pm-8:00 pm

Nonstop3h 18m

$155

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Mon 1/19

7:00 am-11:01 am

Nonstop3h 01m

Fort Myers SW Florida Intl

Sat 2/7

8:46 pm-6:29 pm

2 stops22h 43m

$156

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 1/15

7:35 pm-9:07 am

1 stop12h 32m

Fort Myers SW Florida Intl

Tue 1/20

7:22 am-9:34 am

Nonstop3h 12m

$157

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

6:15 am-8:15 am

Nonstop3h 00m

$163

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 1/7

10:00 am-4:10 pm

1 stop5h 10m

Fort Myers SW Florida Intl

Sat 1/10

6:15 am-8:15 am

Nonstop3h 00m

$173

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 2/21

6:00 am-6:30 pm

1 stop11h 30m

Fort Myers SW Florida Intl

Mon 3/9

7:14 pm-11:42 pm

1 stop5h 28m

$182

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How to get the cheapest flight ticket from Chicago to Fort Myers

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the typical price of a round-trip flight between Chicago and Fort Myers?

What is the cheapest month to fly to Fort Myers?

In general, August is the cheapest month to fly from Chicago to Fort Myers. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $189. If you are unable to visit Fort Myers during the month of August, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $198.

What is the cheapest day to depart on your flight to Fort Myers?

The cheapest day to depart from Chicago to Fort Myers is on a Wednesday when prices can be found for as low as $245. Flights from Chicago to Fort Myers on a Saturday will generally be more expensive and average around $297. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Fort Myers?

The cheapest time of day to fly to Fort Myers is in the afternoon when flights can be purchased for as low as $263. Flights at noon are often more expensive with an average ticket price of $293.

What is the cheapest Chicago to Fort Myers SW Florida Intl flight route?

Fly from Chicago O'Hare Intl to Fort Myers SW Florida Intl for the best Chicago - Fort Myers SW Florida Intl flight prices

How far in advance should I book a flight to Fort Myers?

You are more likely to see cheaper flights to Fort Myers from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Fort Myers for around $258 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Fort Myers from Chicago for as low as $212 on momondo.

What cabin class options are available on Chicago to Fort Myers SW Florida Intl flights?

There are 4 cabin classes available to choose from on Chicago to Fort Myers SW Florida Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Fort Myers flights?

No. A direct flight is the cheapest option for a flight between Chicago to Fort Myers.

How have Chicago to Fort Myers flight prices changed over time?

As of November 2025, prices for Chicago to Fort Myers flights are approximately 55% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Fort Myers

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Fort Myers according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Fort Myers (CHI to RSW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Fort Myers

Best Price Found	$118
Fastest flight time	2h 45m
Direct flights	Every day
Airports in Fort Myers	1 airport

The best one-way flight to Fort Myers from Chicago in the past 72 hours is $118. The best round-trip flight deal from Chicago to Fort Myers found on momondo in the last 72 hours is $186.

The fastest flight from Chicago to Fort Myers takes 2h 45m

Direct flights go from Chicago to Fort Myers every day.

There is 1 airport near Fort Myers: Fort Myers SW Florida Intl (RSW)

Search flight deals

How far is Chicago to Fort Myers SW Florida Intl by plane?
There are 1101.2 mi between Chicago and Fort Myers SW Florida Intl. 2h 45m is a normal flight duration for this route.
When did momondo last update prices for flights from Chicago to Fort Myers SW Florida Intl Airport?
Prices for flights from Chicago to Fort Myers SW Florida Intl Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago to Fort Myers SW Florida Intl Airport?
As of November 2025, there are 7 operators available to choose from for flights from Chicago to Fort Myers SW Florida Intl Airport.
How old do you have to be to fly from Chicago to Fort Myers SW Florida Intl Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Fort Myers SW Florida Intl Airport.
What documentation or ID do you need to fly to Fort Myers SW Florida Intl Airport?
The required travel and health documents for your Fort Myers SW Florida Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Fort Myers SW Florida Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago to Fort Myers?
Based on momondo bookings for flights between Chicago and Fort Myers, the leading plane model is Boeing 737-800, making up 30.31% of the total bookings. Other popular models include Boeing 737 MAX 9 with 13.01%, Airbus A321neo with 11.75%, and Boeing 737 MAX 8 with 10.16%.
What is the most popular airline from Chicago to Fort Myers?
Based on momondo bookings for flights between Chicago and Fort Myers, the leading airline is Spirit Airlines, making up 33% of the total bookings. Other popular airlines include United Airlines with 27%, American Airlines with 24%, and Southwest with 8%.

Best airlines flying from Chicago to Fort Myers

Compare and see reviews for airlines that fly from Chicago to Fort Myers with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $54	Free Cancellation	Rating 5.8 3,099 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $85	Free Cancellation	Rating 6.3 8,158 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $95	Free Cancellation	Rating 7.2 2,905 reviews	Search JetBlue flights
American Airlines	PriceFrom $156	Free Cancellation	Rating 7.2 11,038 reviews	Search American Airlines flights
United Airlines	PriceFrom $166	Free Cancellation	Rating 7.4 9,046 reviews	Search United Airlines flights
Southwest	PriceFrom $172	Free Cancellation	Rating 8.0 4,254 reviews	Search Southwest flights
Delta	PriceFrom $178	Free Cancellation	Rating 7.9 7,998 reviews	Search Delta flights

Southwest Flights From Chicago to Fort Myers
Southwest operates around 21 flights from Chicago to Fort Myers every week. The average price of these flights found in the last 72 hours has been $425, but momondo users have found Southwest deals from Chicago to Fort Myers from as low as $172 round-trip. Southwest has been scored 8.0/10 in 4,254 reviews.
United Airlines Flights From Chicago to Fort Myers
The best United Airlines deal for Chicago to Fort Myers flight tickets found on momondo in the last 72 hours was $166, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $329 round-trip. United Airlines operates 13 flights out of Chicago into Fort Myers in an average week, so prices vary by time and availability. 9,046 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Fort Myers Beach

Sanibel

Cape Coral

Captiva

Estero

North Fort Myers

Boca Grande

Lehigh Acres

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Fort Myers?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Fort Myers from Chicago.

Can I find flights from Chicago to Fort Myers with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Fort Myers from Chicago with this policy.

How can momondo help me find flights from Chicago to Fort Myers?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Fort Myers.

I’m not ready to book a flight from Chicago to Fort Myers right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Fort Myers now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Fort Myers and let you know when they change.

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Cheap flights from Chicago to Fort Myers from $79

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Fort Myers departing on 1/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Our best Spirit Airlines deals on Chicago to Fort Myers flight tickets

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How to get the cheapest flight ticket from Chicago to Fort Myers

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago and Fort Myers?

What is the cheapest month to fly to Fort Myers?

What is the cheapest day to depart on your flight to Fort Myers?

What is the cheapest time of day to depart on your flight to Fort Myers?

The cheapest time of day to fly to Fort Myers is in the afternoon when flights can be purchased for as low as $263. Flights at noon are often more expensive with an average ticket price of $293.

What is the cheapest Chicago to Fort Myers SW Florida Intl flight route?

Fly from Chicago O'Hare Intl to Fort Myers SW Florida Intl for the best Chicago - Fort Myers SW Florida Intl flight prices

How far in advance should I book a flight to Fort Myers?

What cabin class options are available on Chicago to Fort Myers SW Florida Intl flights?

There are 4 cabin classes available to choose from on Chicago to Fort Myers SW Florida Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Fort Myers flights?

No. A direct flight is the cheapest option for a flight between Chicago to Fort Myers.

How have Chicago to Fort Myers flight prices changed over time?

As of November 2025, prices for Chicago to Fort Myers flights are approximately 55% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Chicago to Fort Myers SW Florida Intl?

United Airlines, Southwest, and JetBlue are the most popular carriers operating from Chicago to Fort Myers SW Florida Intl

What airlines fly to Fort Myers?

How often are flights from Chicago to Fort Myers delayed?

Historically, on average around 14% of flights between Chicago and Fort Myers have experienced a delay on any given week. The average delay length over the past 12 months has been 148 minutes.

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

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

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

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 12% of their flights experiencing any sort of delay.

How many flights depart from Chicago to Fort Myers on average per day?

As of November 2025, 15 flights take off from Chicago and land in Fort Myers each day. The most common flight departure time for this route is 7:00AM, with 52% of daily flights taking off at noon.

How many flights depart from Chicago to Fort Myers on average per week?

105 flights are operational weekly from Chicago to Fort Myers as of November 2025. The most popular departure day for this route is Tue, with 26% of flights per week taking off on this day.

When to book flights from Chicago to Fort Myers

Cheap Chicago to Fort Myers (CHI to RSW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Fort Myers

Best Price Found

Fastest flight time

Direct flights

Airports in Fort Myers

How far is Chicago to Fort Myers SW Florida Intl by plane?

When did momondo last update prices for flights from Chicago to Fort Myers SW Florida Intl Airport?

How many operators does momondo search for flights from Chicago to Fort Myers SW Florida Intl Airport?

How old do you have to be to fly from Chicago to Fort Myers SW Florida Intl Airport?

What documentation or ID do you need to fly to Fort Myers SW Florida Intl Airport?

What is the most popular plane model from Chicago to Fort Myers?

What is the most popular airline from Chicago to Fort Myers?

Best airlines flying from Chicago to Fort Myers

Compare and see reviews for airlines that fly from Chicago to Fort Myers with momondo

Southwest Flights From Chicago to Fort Myers

United Airlines Flights From Chicago to Fort Myers

Traveling to a place near Fort Myers?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Fort Myers?

Can I find flights from Chicago to Fort Myers with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Fort Myers?

I’m not ready to book a flight from Chicago to Fort Myers right now. Can momondo alert me if prices change?

An easier way to manage your Fort Myers trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down