Are there direct flights from Chicago to Fort Myers?

Historically, direct flights from Chicago to Fort Myers represent about 31.5% of all available flights across the trailing 90 days. When direct flights are not available, travelers typically encounter flights with stopovers. On average, connecting flights for this route involve 2 stopovers. This indicates that while direct options exist, a significant portion of flights will include at least one stop.

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

The typical direct flight from Chicago to Fort Myers has a duration of approximately 3 hours and 6 minutes. This corresponds to a median flight time of 186 minutes for non-stop journeys. For flights with one stop, the median duration significantly increases to about 10 hours and 27 minutes, or 627 minutes. The distance covered on this route is approximately 1806 kilometers.

How often do Chicago to Fort Myers flight prices drop?

Historically, flight prices for the Chicago to Fort Myers route tend to drop frequently. This suggests that travelers may often find opportunities to secure lower fares. The route has consistently shown price fluctuations, indicating that monitoring prices over time could be beneficial. This pattern has been observed across the trailing 30 days.

Flights From Chicago

To Fort Myers

Cheap Flights from Chicago to Fort Myers

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Deals from

Chicago

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Prices updated 1 day ago

461 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Chicago to Fort Myers

Explore current cheapest deals departing from Chicago to Fort Myers

2026-12-07 – 2026-12-13
CHI - Fort Myers
85% AI deal score
$464
$117
Round trip
2026-12-07 – 2026-12-11
CHI - Fort Myers
82% AI deal score
$476
$145
Round trip
2026-12-06 – 2026-12-07
CHI - Fort Myers
81% AI deal score
$479
$148
Round trip
2026-12-10 – 2026-12-13
CHI - Fort Myers
81% AI deal score
$476
$150
Round trip
2026-12-11 – 2026-12-13
CHI - Fort Myers
81% AI deal score
$479
$152
Round trip
2026-12-06 – 2026-12-13
CHI - Fort Myers
80% AI deal score
$464
$155
Round trip
2026-12-04 – 2026-12-07
CHI - Fort Myers
80% AI deal score
$473
$158
Round trip
2026-12-06 – 2026-12-10
CHI - Fort Myers
79% AI deal score
$476
$168
Round trip
2026-12-07 – 2026-12-14
CHI - Fort Myers
79% AI deal score
$464
$171
Round trip
2026-12-03 – 2026-12-07
CHI - Fort Myers
78% AI deal score
$469
$172
Round trip

Chicago to Fort Myers: Overview

Insights for flights from Chicago to Fort Myers

For travelers looking for cheap flights from Chicago to Fort Myers, fares typically range from $489–$1424, with a median of $959. Right now, current fares are above the typical level, and only 1% of recent fares were classified as a good price.

The journey from Chicago to Fort Myers covers a distance of 1806 kilometers, classifying it as a medium-haul route.

A typical journey from Chicago to Fort Myers takes about 3h 6m, including connections. Since most itineraries connect at least once, you can expect a median of 2 stopovers when not flying direct.

To find the cheapest time to fly from Chicago to Fort Myers, consider traveling in April, when the median fare is $131. May also offers competitive prices with a median of $148, followed by July at a median of $193. New deals appear almost daily, so setting a price alert can be beneficial.

How much is a round trip from Chicago to Fort Myers

Regular price: $199 - $378

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

The regular price range for flights from Chicago to Fort Myers is $199 to $378. The current lowest deal is $219 on Kayak for travel from Oct 7-Oct 10.

now $219

Low $199

High $378

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

Tue, Oct 6

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

American Airlines

$134

$234

One-way

Wed, Oct 7

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

$246

$219

One-way

Wed, Oct 7

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

Southwest Airlines

$395

$229

One-way

Wed, Oct 7

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

Deutsche Luft Hansa

$410

$253

One-way

Sat, Oct 10

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

$396

$219

One-way

Tue, Oct 13

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

$148

$219

One-way

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

5 nights

Dec 13 - Dec 18

$687 → $281

59%

7 nights

Dec 10 - Dec 17

$661 → $269

59%

7 nights

Dec 24 - Dec 31

$687 → $305

56%

1 night

Dec 24 - Dec 25

$706 → $326

54%

Popular Airports to fly from Chicago to Fort Myers

Chicago - Fort Myers route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Chicago to Fort Myers are above the typical level at $959.

📅 Best time to fly

April offers the lowest median prices

Historically, April has the lowest median prices at $131 for this route.

⏱️ Flight duration

Direct flights average 3h 6m

Direct flights from Chicago to Fort Myers typically take 3 hours and 6 minutes.

✈️ Airlines & availability

Connecting flights are more common

Connecting flights make up 68.5% of recent fares for this route.

🏆 Airline highlight

Frontier Airlines offers direct flights

Frontier Airlines provides direct flight options for the Chicago to Fort Myers route.

🎯 Booking tip

Deals are frequent for this route

Deals for flights from Chicago to Fort Myers are frequently available.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers a convenient option for flights from Chicago to Fort Myers.

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

💸 Flights from ~$153

Chicago Midway International (MDW)

Chicago Midway International Airport is another choice for your trip from Chicago to Fort Myers.

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

💸 Flights from ~$282

Chicago Rockford International (RFD)

Chicago Rockford International Airport provides an alternative departure point for flights to Fort Myers.

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

💸 Flights from ~$349

Fort Myers main airports to arrive at

Southwest Florida International (RSW)

Cheapest

Southwest Florida International Airport is a convenient arrival choice for flights to Fort Myers.

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

💸 Flights from ~$153

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 ~$113

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

Dec 12

Fort Myers, United States

85% AI deal score

$1,633

$806

Save $827

United Airlines

Business Class

From ORD

Elite

Oct 14

Fort Myers, United States

83% AI deal score

$1,249

$759

Save $490

United Airlines

Business Class

From ORD

Elite

Dec 08

Fort Myers, United States

82% AI deal score

$1,223

$759

Save $464

United Airlines

Business Class

From ORD

Elite

Oct 14

Fort Myers, United States

81% AI deal score

$1,215

$774

Save $441

United Airlines

Business Class

From ORD

Elite

Dec 12

Fort Myers, United States

81% AI deal score

$1,262

$822

Save $440

United Airlines

Business Class

From ORD

Elite

Sep 29

Fort Myers, United States

81% AI deal score

$1,412

$874

Save $538

United Airlines

Business Class

From ORD

Elite

Sep 29

Fort Myers, United States

81% AI deal score

$1,374

$874

Save $500

United Airlines

Business Class

From ORD

Elite

Sep 30

Fort Myers, United States

81% AI deal score

$1,369

$874

Save $495

United Airlines

Business Class

From ORD

Elite

Jan 07

Fort Myers, United States

79% AI deal score

$1,062

$789

Save $273

United Airlines

Business Class

From ORD

Elite

Oct 17

Fort Myers, United States

78% AI deal score

$1,501

$885

Save $616

From ORD

Elite

Dec 05

Fort Myers, United States

77% AI deal score

$1,200

$812

Save $388

From MDW

Elite

Oct 24

Fort Myers, United States

77% AI deal score

$1,268

$845

Save $423

Frequently Asked Questions About Flights to Fort Myers

Historically, the optimal time to purchase tickets for flights from Chicago to Fort Myers is typically 14-27 days before departure. During this window, the average price observed was $342. In contrast, booking 0-6 days out saw average prices around $893, while booking 60+ days in advance resulted in average prices of $1038. Prices tend to be significantly higher outside of the recommended 14-27 day booking period across the trailing quarter.

A good price for a flight from Chicago to Fort Myers is considered to be $489 or less. Historically, the median price for this route has been $959 across the trailing 90 days. Prices can vary, with 75% of observed prices being $1424 or less. Aiming for a price below $489 typically indicates a favorable deal for this route.

Based on historical data across the trailing 270 days, the cheapest months to fly from Chicago to Fort Myers are typically April, May, and July. In April, the median price was $131, while in May it was $148. July also presented a relatively low median price of $193. The annual median price for this route was $959, indicating significant savings during these months.

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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

The journey from Chicago to Fort Myers covers a distance of 1806 kilometers, classifying it as a medium-haul route.

How much is a round trip from Chicago to Fort Myers

Regular price: $199 - $378

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

The regular price range for flights from Chicago to Fort Myers is $199 to $378. The current lowest deal is $219 on Kayak for travel from Oct 7-Oct 10.

now $219

Low $199

High $378

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

Tue, Oct 6

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

American Airlines

$134

$234

One-way

Wed, Oct 7

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

$246

$219

One-way

Wed, Oct 7

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

Southwest Airlines

$395

$229

One-way

Wed, Oct 7

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

Deutsche Luft Hansa

$410

$253

One-way

Sat, Oct 10

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

$396

$219

One-way

Tue, Oct 13

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

$148

$219

One-way

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

5 nights

Dec 13 - Dec 18

$687 → $281

59%

7 nights

Dec 10 - Dec 17

$661 → $269

59%

7 nights

Dec 24 - Dec 31

$687 → $305

56%

1 night

Dec 24 - Dec 25

$706 → $326

54%

Popular Airports to fly from Chicago to Fort Myers

Chicago - Fort Myers route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Chicago to Fort Myers are above the typical level at $959.

📅 Best time to fly

April offers the lowest median prices

Historically, April has the lowest median prices at $131 for this route.

⏱️ Flight duration

Direct flights average 3h 6m

Direct flights from Chicago to Fort Myers typically take 3 hours and 6 minutes.

✈️ Airlines & availability

Connecting flights are more common

Connecting flights make up 68.5% of recent fares for this route.

🏆 Airline highlight

Frontier Airlines offers direct flights

Frontier Airlines provides direct flight options for the Chicago to Fort Myers route.

🎯 Booking tip

Deals are frequent for this route

Deals for flights from Chicago to Fort Myers are frequently available.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers a convenient option for flights from Chicago to Fort Myers.

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

💸 Flights from ~$153

Chicago Midway International (MDW)

Chicago Midway International Airport is another choice for your trip from Chicago to Fort Myers.

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

💸 Flights from ~$282

Chicago Rockford International (RFD)

Chicago Rockford International Airport provides an alternative departure point for flights to Fort Myers.

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

💸 Flights from ~$349

Fort Myers main airports to arrive at

Southwest Florida International (RSW)

Cheapest

Southwest Florida International Airport is a convenient arrival choice for flights to Fort Myers.

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

💸 Flights from ~$153

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

78% AI deal score

$1,501

$885

Save $616

From ORD

Elite

Dec 05

Fort Myers, United States

77% AI deal score

$1,200

$812

Save $388

From MDW

Elite

Oct 24

Fort Myers, United States

77% AI deal score

$1,268

$845

Save $423

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 above the typical level

April offers the lowest median prices

Direct flights average 3h 6m

Connecting flights are more common

Frontier Airlines offers direct flights

Deals are frequent for this route

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

Dec 12

Oct 14

Dec 08

Oct 14

Dec 12

Sep 29

Sep 29

Sep 30

Jan 07

Oct 17

Dec 05

Oct 24

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 above the typical level

April offers the lowest median prices

Direct flights average 3h 6m

Connecting flights are more common

Frontier Airlines offers direct flights

Deals are frequent for this route

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

Dec 12

Oct 14

Dec 08

Oct 14

Dec 12

Sep 29

Sep 29

Sep 30

Jan 07

Oct 17

Dec 05

Oct 24

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?