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 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.

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

As of December 2025, 18 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 53% of daily flights taking off at noon.

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

129 flights are operational weekly from Chicago to Fort Myers as of December 2025. The most popular departure day for this route is Thu, with 18% of flights per week taking off on this day.

How often are flights from Chicago to Fort Myers delayed?

Historically, on average around 15% 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 149 minutes.

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 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.

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 December 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.

$59 Cheap Flights from Chicago to Fort Myers in 2025/26

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

Prices are currently low for flights on this route. Typical prices usually range from $230 to $555. The lowest price recently found on this route was $110.

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Find the cheapest flights from Chicago to Fort Myers

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:30 am - 10:39 am

ORD

RSW

3h 09mnonstop

12:27 pm - 3:02 pm

RSW

ORD

3h 35mnonstop

$110Frontier

Sun, Mar 1 - Sun, Mar 8

7:00 am - 11:01 am

ORD

RSW

3h 01mnonstop

7:31 am - 9:43 am

RSW

ORD

3h 12mnonstop

$111Spirit Airlines

Thu, Jan 15 - Sun, Jan 18

7:21 pm - 11:24 pm

ORD

RSW

3h 03mnonstop

1:29 pm - 10:39 pm

RSW

ORD

10h 10m1 stop

$114Multiple Airlines

Sat, Jan 31 - Sat, Feb 28

5:50 am - 12:18 pm

ORD

RSW

5h 28m1 stop

7:45 pm - 10:04 pm

RSW

ORD

3h 19mnonstop

$118Multiple Airlines

Mon, Jan 12 - Thu, Jan 22

12:45 pm - 4:47 pm

ORD

RSW

3h 02mnonstop

12:10 pm - 7:36 pm

RSW

ORD

8h 26m1 stop

$120Multiple Airlines

Sat, Jan 10 - Sat, Jan 17

7:00 am - 11:02 am

ORD

RSW

3h 02mnonstop

7:14 pm - 12:01 am

RSW

ORD

5h 47m1 stop

$121Frontier

Sat, Feb 21 - Mon, Mar 9

1:13 pm - 5:30 pm

ORD

RSW

3h 17mnonstop

12:10 pm - 7:36 pm

RSW

ORD

8h 26m1 stop

$122Multiple Airlines

Sat, Jan 17 - Sat, Jan 31

7:20 pm - 11:23 pm

ORD

RSW

3h 03mnonstop

7:00 am - 9:12 am

RSW

ORD

3h 12mnonstop

$124Spirit Airlines

Sat, Feb 14 - Sun, Feb 22

6:05 pm - 9:50 pm

MDW

RSW

2h 45mnonstop

6:15 am - 8:15 am

RSW

MDW

3h 00mnonstop

$157Southwest

Sat, Jan 24 - Sat, Jan 31

6:05 pm - 9:50 pm

MDW

RSW

2h 45mnonstop

5:00 am - 7:00 am

RSW

MDW

3h 00mnonstop

$177Southwest

Sat, Jan 10 - Sun, Jan 11

Frontier flights from Chicago to Fort Myers

Our best Frontier deals on Chicago to Fort Myers flight tickets

Frontier

Mar 1

ORD6:30 amChicago O'Hare Intl

3h 09m

RSW10:39 amFort Myers SW Florida Intl

Mar 8

RSW12:27 pmFort Myers SW Florida Intl

3h 35m

ORD3:02 pmChicago O'Hare Intl

$110

Find similar

Frontier

Feb 22

MDW6:00 amChicago Midway

11h 30m

1 stop

RSW6:30 pmFort Myers SW Florida Intl

Feb 28

RSW7:25 pmFort Myers SW Florida Intl

5h 00m

1 stop

MDW11:25 pmChicago Midway

$155

Find similar

Frontier

Feb 21

MDW6:00 amChicago Midway

11h 30m

1 stop

RSW6:30 pmFort Myers SW Florida Intl

Feb 28

RSW7:25 pmFort Myers SW Florida Intl

5h 00m

1 stop

MDW11:25 pmChicago Midway

$168

Find similar

Spirit Airlines flights from Chicago to Fort Myers

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

Spirit Airlines

Jan 15

ORD7:00 amChicago O'Hare Intl

3h 01m

RSW11:01 amFort Myers SW Florida Intl

Jan 18

RSW7:31 amFort Myers SW Florida Intl

3h 12m

ORD9:43 amChicago O'Hare Intl

$111

Find similar

Spirit Airlines

Jan 3

ORD4:55 pmChicago O'Hare Intl

3h 05m

RSW9:00 pmFort Myers SW Florida Intl

Jan 11

RSW7:31 amFort Myers SW Florida Intl

3h 12m

ORD9:43 amChicago O'Hare Intl

$112

Find similar

Spirit Airlines

Jan 15

ORD7:00 amChicago O'Hare Intl

3h 01m

RSW11:01 amFort Myers SW Florida Intl

Jan 18

RSW7:31 amFort Myers SW Florida Intl

3h 12m

ORD9:43 amChicago O'Hare Intl

$113

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 3/1

6:30 am-10:39 am

Nonstop3h 09m

Fort Myers SW Florida Intl

Sun 3/8

12:27 pm-3:02 pm

Nonstop3h 35m

$110

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 1/15

7:00 am-11:01 am

Nonstop3h 01m

Fort Myers SW Florida Intl

Sun 1/18

7:31 am-9:43 am

Nonstop3h 12m

$111

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 1/31

7:21 pm-11:24 pm

Nonstop3h 03m

Fort Myers SW Florida Intl

Sat 2/28

1:29 pm-10:39 pm

1 stop10h 10m

$114

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Mon 1/12

5:50 am-12:18 pm

1 stop5h 28m

Fort Myers SW Florida Intl

Thu 1/22

7:45 pm-10:04 pm

Nonstop3h 19m

$118

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 1/10

12:45 pm-4:47 pm

Nonstop3h 02m

Fort Myers SW Florida Intl

Sat 1/17

12:10 pm-7:36 pm

1 stop8h 26m

$120

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 2/21

7:00 am-11:02 am

Nonstop3h 02m

Fort Myers SW Florida Intl

Mon 3/9

7:14 pm-12:01 am

1 stop5h 47m

$121

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 1/17

1:13 pm-5:30 pm

Nonstop3h 17m

Fort Myers SW Florida Intl

Sat 1/31

12:10 pm-7:36 pm

1 stop8h 26m

$122

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 2/14

7:20 pm-11:23 pm

Nonstop3h 03m

Fort Myers SW Florida Intl

Sun 2/22

7:00 am-9:12 am

Nonstop3h 12m

$124

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 1/24

6:05 pm-9:50 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Sat 1/31

6:15 am-8:15 am

Nonstop3h 00m

$157

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 1/10

6:05 pm-9:50 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Sun 1/11

5:00 am-7:00 am

Nonstop3h 00m

$177

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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 $296. 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 $266. Flights at noon are often more expensive with an average ticket price of $296.

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 $215 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 December 2025, prices for Chicago to Fort Myers flights are approximately 4% cheaper 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	$98
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 $98. The best round-trip flight deal from Chicago to Fort Myers found on momondo in the last 72 hours is $177.

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 in Fort Myers. From Chicago there are direct flights to 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 December 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 29.29% of the total bookings. Other popular models include Boeing 737 MAX 9 with 13.43%, Airbus A321neo with 11.48%, and Boeing 737 MAX 8 with 9.09%.
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 25%, 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 $53	Free Cancellation	Rating 5.8 3,084 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $80	Free Cancellation	Rating 6.3 8,175 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $143	Free Cancellation	Rating 7.2 2,898 reviews	Search JetBlue flights
American Airlines	PriceFrom $156	Free Cancellation	Rating 7.2 11,048 reviews	Search American Airlines flights
United Airlines	PriceFrom $164	Free Cancellation	Rating 7.4 9,095 reviews	Search United Airlines flights
Southwest	PriceFrom $171	Free Cancellation	Rating 7.9 4,252 reviews	Search Southwest flights
Delta	PriceFrom $178	Free Cancellation	Rating 7.9 8,008 reviews	Search Delta flights

Southwest Flights From Chicago to Fort Myers
Southwest operates around 12 flights from Chicago to Fort Myers every week. The average price of these flights found in the last 72 hours has been $419, but momondo users have found Southwest deals from Chicago to Fort Myers from as low as $171 round-trip. Southwest has been scored 7.9/10 in 4,252 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 $164, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $328 round-trip. United Airlines operates 20 flights out of Chicago into Fort Myers in an average week, so prices vary by time and availability. 9,095 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.

An easier way to manage your Fort Myers trip

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Cheap flights from Chicago to Fort Myers from $76

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 3/5. 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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How to get the cheapest flight ticket from Chicago to Fort Myers

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 $266. Flights at noon are often more expensive with an average ticket price of $296.

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 December 2025, prices for Chicago to Fort Myers flights are approximately 4% cheaper 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 15% 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 149 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 December 2025, 18 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 53% of daily flights taking off at noon.

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

129 flights are operational weekly from Chicago to Fort Myers as of December 2025. The most popular departure day for this route is Thu, with 18% 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

Daily price changes in your inbox - only with Price Alerts.