Are there direct flights from Chicago to Fort Myers?

Yes, direct flights from Chicago to Fort Myers are available. Historically, approximately 31.5% of flights on this route have been direct. For flights that include stopovers, the median number of stopovers observed was 2. Travelers have options for both direct and connecting services.

How many hours is the flight from Chicago to Fort Myers?

The typical direct flight from Chicago to Fort Myers has a duration of 3 hours and 6 minutes, covering a distance of 1806 kilometers. For flights with one stop, the median duration observed was significantly longer, at 10 hours and 27 minutes. Travelers should consider these durations when planning their journey.

How often do Chicago to Fort Myers flight prices drop?

Historically, flight prices for the Chicago to Fort Myers route are classified as dropping frequently. This suggests that travelers may have regular opportunities to find reduced fares. Monitoring prices in the trailing 30 days can be beneficial for securing a good deal on this route.

Flights From Chicago

To Fort Myers

Cheap Flights from Chicago to Fort Myers

Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights to Fort Myers

Prices updated 11 days ago

406 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 2, 2026.)

Today’s best flight deals from Chicago to Fort Myers

Explore current cheapest deals departing from Chicago to Fort Myers

2026-12-10 – 2026-12-13
CHI - Fort Myers
82% AI deal score
$604
$180
Round trip
2026-09-05 – 2026-09-10
CHI - Fort Myers
76% AI deal score
$283
$184
Round trip
2026-09-10 – 2026-09-14
CHI - Fort Myers
48% AI deal score
$162
$195
Round trip
2026-09-14 – 2026-09-16
CHI - Fort Myers
48% AI deal score
$161
$195
Round trip
2026-09-17 – 2026-09-23
CHI - Fort Myers
48% AI deal score
$153
$195
Round trip
2026-09-16 – 2026-09-22
CHI - Fort Myers
48% AI deal score
$153
$195
Round trip
2026-10-05 – 2026-10-07
CHI - Fort Myers
69% AI deal score
$245
$195
Round trip
2026-10-06 – 2026-10-10
CHI - Fort Myers
69% AI deal score
$246
$195
Round trip
2026-10-19 – 2026-10-28
CHI - Fort Myers
49% AI deal score
$141
$195
Round trip
2026-10-08 – 2026-10-26
CHI - Fort Myers
48% AI deal score
$129
$195
Round trip

Chicago to Fort Myers: Overview

Insights for flights from Chicago to Fort Myers

Fares for flights from Chicago to Fort Myers typically range from $489–$1424, with a median price of $959. Right now, current fares are above the typical level for this route. Only 1% of recent fares were classified as a good price, indicating that finding cheap flights from Chicago to Fort Myers requires careful planning.

The cheapest time to fly from Chicago to Fort Myers is during the spring and summer months. April offers the lowest median fare at $131, followed by May with a median of $148. July also presents a more affordable option, with a median fare of $193.

A typical journey from Chicago to Fort Myers takes about 3h 6m. This route is classified as medium-haul, covering a distance of 1806 kilometers.

For this route, most itineraries connect at least once, with only 31.5% of recent fares being non-stop. When connecting, the median number of stopovers is 2. New deals for this route appear almost daily, suggesting frequent opportunities to find competitive pricing if you are flexible with connections.

How much is a round trip from Chicago to Fort Myers

Regular price: $394 - $1,133

Prices for flights from Chicago to Fort Myers are currently below the regular range.

The regular price range for this route is $394 to $1133. The current lowest deal is $244 with Frontier Airlines for travel from Dec 3-Dec 6.

now $244

Low $394

High $1,133

The cheapest time to fly from Chicago to Fort Myers

The cheapest month to fly from Chicago to Fort Myers is May, with a median price of $167. The most expensive month is December, with a median price of $1404. Prices are generally lower from January to November.

May

Cheapest

Flights from $167

December

Most Expensive

Flights from $1,404

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Fort Myers

Frontier Airlines

Last-minute flights going from Chicago to Fort Myers

Sun, Aug 2

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

Southwest Airlines

$650

$483

One-way

Mon, Aug 3

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

$650

$467

One-way

Tue, Aug 4

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

$629

$429

One-way

Tue, Aug 4

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

$606

$429

One-way

Tue, Aug 4

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

Southwest Airlines

$624

$473

One-way

Wed, Aug 5

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

$610

$429

One-way

Biggest price drops on these dates for flights from Chicago to Fort Myers

7 nights

Dec 24 - Dec 31

$819 → $270

67%

5 nights

Dec 24 - Dec 29

$836 → $324

61%

4 nights

Dec 14 - Dec 18

$809 → $313

61%

6 nights

Dec 24 - Dec 30

$819 → $324

60%

Popular Airports to fly from Chicago to Fort Myers

Chicago - Fort Myers route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Chicago to Fort Myers are below the typical level at $244.

📅 Best time to fly

Fly in May for the best prices

Historically, May is the cheapest month to fly, with a median price of $167.

⏱️ Flight duration

Direct flights take 3h 6m

The median flight time for a direct flight from Chicago to Fort Myers is 3h 6m.

✈️ Airlines & availability

Frontier Airlines offers direct flights

Frontier Airlines provides direct flights on this route, with frequent deals available.

🏆 Airline highlight

Frontier Airlines: 1 direct deal

Frontier Airlines has offered 1 direct deal from Chicago to Fort Myers recently.

🎯 Booking tip

Consider connecting flights for more options

Connecting flights are dominant for this route, with a median of 2 stopovers.

Chicago main airports to depart from

Chicago Midway International (MDW)

Cheapest

Chicago Midway International offers a convenient departure point for flights to Fort Myers.

📍 ~14 km from Chicago city center (reachable by car or train).

💸 Flights from ~$188

Chicago Rockford International (RFD)

Chicago Rockford International provides another option for flights from the wider Chicago area to Fort Myers.

📍 ~126 km from Chicago city center (reachable by car).

💸 Flights from ~$349

O Hare International (ORD)

O Hare International is a major hub providing many flight options to Fort Myers.

📍 ~25 km from Chicago city center (reachable by car or train).

💸 Flights from ~$188

Fort Myers main airports to arrive at

Southwest Florida International (RSW)

Cheapest

Southwest Florida International Airport is a good option for flights from Chicago to Fort Myers.

📍 ~16 km from Fort Myers (reachable by car)

💸 Flights from ~$188

Airports nearby Fort Myers used as alternative

Punta Gorda (PGD)

Punta Gorda is a useful alternative for budget travel due to its proximity to Fort Myers.

📍 ~40 km from Fort Myers (reachable by car)

💸 Flights from ~$102

Business & First Class Flight Deals to Fort Myers

Discover luxury on the budget with premium cabin class on flights from Chicago to Fort Myers.

Elite

Best Elite deals to Fort Myers

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From ORD

Elite

Sep 02

Fort Myers, United States

85% AI deal score

$1,358

$735

Save $623

United Airlines

Business Class

From ORD

Elite

Sep 04

Fort Myers, United States

85% AI deal score

$1,710

$820

Save $890

United Airlines

Business Class

From ORD

Elite

Sep 08

Fort Myers, United States

84% AI deal score

$1,353

$734

Save $619

United Airlines

Business Class

From ORD

Elite

Aug 26

Fort Myers, United States

84% AI deal score

$1,529

$841

Save $688

United Airlines

Business Class

From ORD

Elite

Sep 24

Fort Myers, United States

84% AI deal score

$1,610

$845

Save $765

United Airlines

Business Class

From ORD

Elite

Sep 05

Fort Myers, United States

82% AI deal score

$1,710

$735

Save $975

United Airlines

Business Class

From ORD

Elite

Oct 24

Fort Myers, United States

81% AI deal score

$1,161

$744

Save $417

United Airlines

Business Class

From MDW

Fort Myers, United States

79% AI deal score

$1,003

$725

Save $278

United Airlines

Business Class

Frequently Asked Questions About Flights to Fort Myers

Historically, the optimal booking window for flights from Chicago to Fort Myers is typically 14-27 days before departure. During this period, the average price observed was $342. Prices tend to be higher outside this window, with flights booked 0-6 days out averaging $893 and those booked 60+ days out averaging $1038. Planning your purchase within this timeframe can lead to more favorable pricing.

Across the trailing quarter, a good price for a flight from Chicago to Fort Myers is considered to be $489 or less. The median price for this route was $959. Prices can vary, with 75% of observed fares being $1424 or less. Aiming for a price at or below the $489 threshold indicates a favorable deal.

Historically, the cheapest months to fly from Chicago to Fort Myers include April, with a median price of $131, and May, with a median price of $148. July also showed a relatively low median price of $193. The annual median price for this route was $959. Travelers looking for lower fares should consider these months for their trips.

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Flights to Fort Myers from other cities

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Chicago to Fort Myers: Overview

Insights for flights from Chicago to Fort Myers

A typical journey from Chicago to Fort Myers takes about 3h 6m. This route is classified as medium-haul, covering a distance of 1806 kilometers.

How much is a round trip from Chicago to Fort Myers

Regular price: $394 - $1,133

Prices for flights from Chicago to Fort Myers are currently below the regular range.

The regular price range for this route is $394 to $1133. The current lowest deal is $244 with Frontier Airlines for travel from Dec 3-Dec 6.

now $244

Low $394

High $1,133

The cheapest time to fly from Chicago to Fort Myers

May

Cheapest

Flights from $167

December

Most Expensive

Flights from $1,404

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Fort Myers

Frontier Airlines

Last-minute flights going from Chicago to Fort Myers

Sun, Aug 2

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

Southwest Airlines

$650

$483

One-way

Mon, Aug 3

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

$650

$467

One-way

Tue, Aug 4

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

$629

$429

One-way

Tue, Aug 4

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

$606

$429

One-way

Tue, Aug 4

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

Southwest Airlines

$624

$473

One-way

Wed, Aug 5

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

$610

$429

One-way

Biggest price drops on these dates for flights from Chicago to Fort Myers

7 nights

Dec 24 - Dec 31

$819 → $270

67%

5 nights

Dec 24 - Dec 29

$836 → $324

61%

4 nights

Dec 14 - Dec 18

$809 → $313

61%

6 nights

Dec 24 - Dec 30

$819 → $324

60%

Popular Airports to fly from Chicago to Fort Myers

Chicago - Fort Myers route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Chicago to Fort Myers are below the typical level at $244.

📅 Best time to fly

Fly in May for the best prices

Historically, May is the cheapest month to fly, with a median price of $167.

⏱️ Flight duration

Direct flights take 3h 6m

The median flight time for a direct flight from Chicago to Fort Myers is 3h 6m.

✈️ Airlines & availability

Frontier Airlines offers direct flights

Frontier Airlines provides direct flights on this route, with frequent deals available.

🏆 Airline highlight

Frontier Airlines: 1 direct deal

Frontier Airlines has offered 1 direct deal from Chicago to Fort Myers recently.

🎯 Booking tip

Consider connecting flights for more options

Connecting flights are dominant for this route, with a median of 2 stopovers.

Chicago main airports to depart from

Chicago Midway International (MDW)

Cheapest

Chicago Midway International offers a convenient departure point for flights to Fort Myers.

📍 ~14 km from Chicago city center (reachable by car or train).

💸 Flights from ~$188

Chicago Rockford International (RFD)

Chicago Rockford International provides another option for flights from the wider Chicago area to Fort Myers.

📍 ~126 km from Chicago city center (reachable by car).

💸 Flights from ~$349

O Hare International (ORD)

O Hare International is a major hub providing many flight options to Fort Myers.

📍 ~25 km from Chicago city center (reachable by car or train).

💸 Flights from ~$188

Fort Myers main airports to arrive at

Southwest Florida International (RSW)

Cheapest

Southwest Florida International Airport is a good option for flights from Chicago to Fort Myers.

📍 ~16 km from Fort Myers (reachable by car)

💸 Flights from ~$188

Airports nearby Fort Myers used as alternative

Punta Gorda (PGD)

Punta Gorda is a useful alternative for budget travel due to its proximity to Fort Myers.

Fort Myers, United States

81% AI deal score

$1,565

$785

Save $780

From ORD

Elite

Sep 11

Fort Myers, United States

81% AI deal score

$1,353

$854

Save $499

United Airlines

Business Class

From ORD

Elite

Oct 10

Fort Myers, United States

80% AI deal score

$1,284

$844

Save $440

United Airlines

Business Class

From ORD

Elite

Oct 08

Fort Myers, United States

80% AI deal score

$1,281

$845

Save $436

United Airlines

Business Class

From ORD

Elite

Sep 07

Fort Myers, United States

79% AI deal score

$1,003

$725

Save $278

United Airlines

Business Class

Frequently Asked Questions About Flights to Fort Myers

Cheap Flights from Chicago to Fort Myers

Today’s best flight deals from Chicago to Fort Myers

Chicago to Fort Myers: Overview

Insights for flights from Chicago to Fort Myers

How much is a round trip from Chicago to Fort Myers

The cheapest time to fly from Chicago to Fort Myers

Direct flights from Chicago to Fort Myers

Last-minute flights going from Chicago to Fort Myers

Biggest price drops on these dates for flights from Chicago to Fort Myers

Popular Airports to fly from Chicago to Fort Myers

Chicago - Fort Myers route insights

Recent fares are below the typical level

Fly in May for the best prices

Direct flights take 3h 6m

Frontier Airlines offers direct flights

Frontier Airlines: 1 direct deal

Consider connecting flights for more options

Chicago main airports to depart from

Fort Myers main airports to arrive at

Airports nearby Fort Myers used as alternative

Business & First Class Flight Deals to Fort Myers

Best Elite deals to Fort Myers

Sep 02

Sep 04

Sep 08

Aug 26

Sep 24

Sep 05

Oct 24

Sep 24

Sep 11

Oct 10

Oct 08

Sep 07

Frequently Asked Questions About Flights to Fort Myers

When should I buy Chicago to Fort Myers tickets?

How much should a flight from Chicago to Fort Myers cost?

When is the cheapest time of year to fly from Chicago to Fort Myers?

Are there direct flights from Chicago to Fort Myers?

How many hours is the flight from Chicago to Fort Myers?

How often do Chicago to Fort Myers flight prices drop?

Related routes

More routes from Chicago

Flights to Fort Myers from other cities

Chicago to Fort Myers: Overview

Insights for flights from Chicago to Fort Myers

How much is a round trip from Chicago to Fort Myers

The cheapest time to fly from Chicago to Fort Myers

Direct flights from Chicago to Fort Myers

Last-minute flights going from Chicago to Fort Myers

Biggest price drops on these dates for flights from Chicago to Fort Myers

Popular Airports to fly from Chicago to Fort Myers

Chicago - Fort Myers route insights

Recent fares are below the typical level

Fly in May for the best prices

Direct flights take 3h 6m

Frontier Airlines offers direct flights

Frontier Airlines: 1 direct deal

Consider connecting flights for more options

Chicago main airports to depart from

Fort Myers main airports to arrive at

Airports nearby Fort Myers used as alternative

Business & First Class Flight Deals to Fort Myers

Best Elite deals to Fort Myers

Sep 02

Sep 04

Sep 08

Aug 26

Sep 24

Sep 05

Oct 24

Sep 24

Sep 11

Oct 10

Oct 08

Sep 07

Frequently Asked Questions About Flights to Fort Myers

When should I buy Chicago to Fort Myers tickets?

How much should a flight from Chicago to Fort Myers cost?

When is the cheapest time of year to fly from Chicago to Fort Myers?