Are there direct flights from Chicago to Fort Myers?

In the trailing 90 days, approximately 32.6% of flights from Chicago to Fort Myers were direct. For itineraries that included connecting flights, the median number of stopovers was 2. Travelers seeking a more direct journey should consider that a significant portion of available flights may involve 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 median duration of 3 hours and 5 minutes, covering a distance of 1806 kilometers. Flights with one stop, however, historically have a significantly longer median duration of 8 hours and 43 minutes. Travelers should account for these differences when planning their journey.

How often do Chicago to Fort Myers flight prices drop?

Historically, flight prices for the Chicago to Fort Myers route experience frequent drops. This indicates that travelers may often find opportunities for more favorable pricing. Monitoring prices over time could 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 7 days ago

483 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Oct 26, 2026.)

Today’s best flight deals from Chicago to Fort Myers

Explore current cheapest deals departing from Chicago to Fort Myers

2026-12-13 – 2026-12-14
CHI - Fort Myers
85% AI deal score
$445
$110
Round trip
2026-12-13 – 2027-01-07
CHI - Fort Myers
82% AI deal score
$340
$113
Round trip
2026-12-13 – 2026-12-23
CHI - Fort Myers
83% AI deal score
$385
$113
Round trip
2026-12-13 – 2026-12-29
CHI - Fort Myers
82% AI deal score
$357
$113
Round trip
2026-12-07 – 2026-12-14
CHI - Fort Myers
83% AI deal score
$419
$118
Round trip
2026-12-07 – 2026-12-23
CHI - Fort Myers
81% AI deal score
$357
$118
Round trip
2026-12-07 – 2026-12-29
CHI - Fort Myers
81% AI deal score
$345
$118
Round trip
2026-12-14 – 2026-12-23
CHI - Fort Myers
81% AI deal score
$398
$128
Round trip
2026-12-14 – 2026-12-29
CHI - Fort Myers
80% AI deal score
$358
$128
Round trip
2026-12-14 – 2027-01-07
CHI - Fort Myers
79% AI deal score
$340
$128
Round trip

Chicago to Fort Myers: Overview

Insights for flights from Chicago to Fort Myers

For cheap flights from Chicago to Fort Myers, fares typically range from $432–$1135, with a median of $698. Right now, current fares are below the typical level, and about 26% of recent fares were classified as a good price. New deals appear almost daily, offering frequent opportunities to find competitive pricing for this route.

A typical journey from Chicago to Fort Myers covers a distance of 1806 kilometers, classifying it as a medium-haul flight. This distance means you can expect a moderate travel duration, bridging the gap between short regional trips and longer international journeys.

The typical journey time for flights from Chicago to Fort Myers is 3h 5m. Since most itineraries connect at least once, this duration reflects the median time for all flights, including those with stopovers. For connecting flights specifically, the median journey time is 22h 15m, while non-stop flights have a median duration of 3h 5m.

When is the cheapest time to fly from Chicago to Fort Myers? The most affordable months to travel are October, with a median fare of $372, followed by June and April, both showing median fares of $395. These months present the best opportunities for travelers seeking lower prices on this route.

Regarding direct flights from Chicago to Fort Myers, only 32.6% of recent fares were non-stop. This indicates that most itineraries connect at least once, with the typical number of connections for these flights being 2. Travelers should account for potential layovers when planning their trip.

How much is a round trip from Chicago to Fort Myers

Regular price: $243 - $1,076

Prices are currently below the regular range.

The regular price range for flights from Chicago to Fort Myers is $243-$1076. The current lowest deal is $110 with Frontier Airlines for travel from Dec 13-Jan 7.

now $110

Low $243

High $1,076

The cheapest time to fly from Chicago to Fort Myers

The cheapest month to fly from Chicago to Fort Myers is October, with a median price of $371. The most expensive month is March, with a median price of $885. Prices are generally lower from January to October.

October

Cheapest

Flights from $371

March

Most Expensive

Flights from $885

Jan

Feb

Mar

Apr

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, Nov 8

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

American Airlines

$153

$353

One-way

Tue, Nov 10

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

United Airlines

$162

$352

One-way

Wed, Nov 11

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

United Airlines

$154

$353

One-way

Thu, Nov 12

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

United Airlines

$174

$352

One-way

Sat, Nov 14

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

United Airlines

$158

$352

One-way

Sun, Nov 15

⌛ Last-Minute

RFD - Fort Myers

Chicago (RFD) - Fort Myers (RSW)

Allegiant Air

$326

$290

One-way

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

6 nights

Dec 17 - Dec 23

$636 → $194

69%

4 nights

Dec 17 - Dec 21

$668 → $245

63%

5 nights

Dec 17 - Dec 22

$657 → $235

64%

1 night

Dec 13 - Dec 14

$445 → $110

75%

Popular Airports to fly from Chicago to Fort Myers

Chicago - Fort Myers route insights

💸 Price insights

Recent fares below the typical level

Recent fares from Chicago to Fort Myers are below the typical level at a median of $698.

📅 Best time to fly

October offers the lowest median price

Historically, October is the cheapest month to fly, with a median price of $372.

⏱️ Flight duration

Direct flights average 3h 5m

The typical direct flight from Chicago to Fort Myers takes 3h 5m.

✈️ Airlines & availability

Connecting flights are more common

Connecting flights are more common, with 32.6% of recent flights being direct.

🏆 Airline highlight

Frontier Airlines offers direct deals

Frontier Airlines has offered direct deals on this route recently.

🎯 Booking tip

Deals are frequent on this route

Deals on flights from Chicago to Fort Myers are frequent, appearing every 30 days.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers flights to Fort Myers and is often a budget-friendly option.

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

💸 Flights from ~$75

Chicago Midway International (MDW)

Chicago Midway International Airport is a convenient option for flights to Fort Myers.

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

💸 Flights from ~$219

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 ~$377

Fort Myers main airports to arrive at

Southwest Florida International (RSW)

Cheapest

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

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

💸 Flights from ~$75

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 ~$109

Business & First Class Flight Deals to Fort Myers

71% AI deal score

$3,656

$2,553

Save $1,103

Alaska Airlines, Inc.

Business Class

From MDW

Elite

Jan 24

Fort Myers, United States

70% AI deal score

$4,611

$3,306

Save $1,305

Aeroméxico, +1

Business Class

From MDW

Elite

Jan 24

Fort Myers, United States

70% AI deal score

$4,575

$3,306

Save $1,269

Aeroméxico, +1

Business Class

From MDW

Elite

Jan 24

Fort Myers, United States

70% AI deal score

$4,872

$3,306

Save $1,566

Aeroméxico, +1

Business Class

From MDW

Elite

Jan 24

Fort Myers, United States

70% AI deal score

$4,596

$3,387

Save $1,209

Aeroméxico, +1

Business Class

From ORD

Elite

Feb 25

Fort Myers, United States

69% AI deal score

$3,939

$3,206

Save $733

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Feb 20

Fort Myers, United States

69% AI deal score

$1,031

$869

Save $162

From ORD

Elite

Oct 27

Fort Myers, United States

69% AI deal score

$1,967

$1,449

Save $518

From ORD

Elite

Dec 03

Fort Myers, United States

68% AI deal score

$3,656

$3,107

Save $549

Air Canada, +1

Business Class

From ORD

Elite

Dec 10

Fort Myers, United States

68% AI deal score

$3,546

$3,126

Save $420

Air Canada, +1

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. Across the trailing quarter, prices averaged around $1715 during this period. Booking too early, such as 60+ days out, showed an average price of $1830. Conversely, waiting until 0-6 days before departure often results in significantly higher prices, with an average of $2468.

In the trailing 90 days, a good price for a flight from Chicago to Fort Myers was considered to be $432 or less. The median price for this route was $698. Prices above $1135 were observed for the more expensive tickets. These figures provide a historical benchmark for travelers planning their trips.

Historically, the cheapest months to fly from Chicago to Fort Myers include October, with a median price of $372, and both June and April, each with a median price of $395. The annual median price for this route is $698. These months typically offer more budget-friendly options compared to other times of the year.

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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

How much is a round trip from Chicago to Fort Myers

Regular price: $243 - $1,076

Prices are currently below the regular range.

The regular price range for flights from Chicago to Fort Myers is $243-$1076. The current lowest deal is $110 with Frontier Airlines for travel from Dec 13-Jan 7.

now $110

Low $243

High $1,076

The cheapest time to fly from Chicago to Fort Myers

October

Cheapest

Flights from $371

March

Most Expensive

Flights from $885

Jan

Feb

Mar

Apr

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, Nov 8

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

American Airlines

$153

$353

One-way

Tue, Nov 10

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

United Airlines

$162

$352

One-way

Wed, Nov 11

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

United Airlines

$154

$353

One-way

Thu, Nov 12

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

United Airlines

$174

$352

One-way

Sat, Nov 14

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

United Airlines

$158

$352

One-way

Sun, Nov 15

⌛ Last-Minute

RFD - Fort Myers

Chicago (RFD) - Fort Myers (RSW)

Allegiant Air

$326

$290

One-way

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

6 nights

Dec 17 - Dec 23

$636 → $194

69%

4 nights

Dec 17 - Dec 21

$668 → $245

63%

5 nights

Dec 17 - Dec 22

$657 → $235

64%

1 night

Dec 13 - Dec 14

$445 → $110

75%

Popular Airports to fly from Chicago to Fort Myers

Chicago - Fort Myers route insights

💸 Price insights

Recent fares below the typical level

Recent fares from Chicago to Fort Myers are below the typical level at a median of $698.

📅 Best time to fly

October offers the lowest median price

Historically, October is the cheapest month to fly, with a median price of $372.

⏱️ Flight duration

Direct flights average 3h 5m

The typical direct flight from Chicago to Fort Myers takes 3h 5m.

✈️ Airlines & availability

Connecting flights are more common

Connecting flights are more common, with 32.6% of recent flights being direct.

🏆 Airline highlight

Frontier Airlines offers direct deals

Frontier Airlines has offered direct deals on this route recently.

🎯 Booking tip

Deals are frequent on this route

Deals on flights from Chicago to Fort Myers are frequent, appearing every 30 days.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers flights to Fort Myers and is often a budget-friendly option.

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

💸 Flights from ~$75

Chicago Midway International (MDW)

Chicago Midway International Airport is a convenient option for flights to Fort Myers.

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

💸 Flights from ~$219

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 ~$377

Fort Myers main airports to arrive at

Southwest Florida International (RSW)

Cheapest

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

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

💸 Flights from ~$75

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 ~$109

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 MDW

Elite

Oct 31

Fort Myers, United States

78% AI deal score

$1,699

$1,003

Save $696

From ORD

Fort Myers, United States

69% AI deal score

$1,031

$869

Save $162

From ORD

Elite

Oct 27

Fort Myers, United States

69% AI deal score

$1,967

$1,449

Save $518

From ORD

Elite

Dec 03

Fort Myers, United States

68% AI deal score

$3,656

$3,107

Save $549

Air Canada, +1

Business Class

From ORD

Elite

Dec 10

Fort Myers, United States

68% AI deal score

$3,546

$3,126

Save $420

Air Canada, +1

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 below the typical level

October offers the lowest median price

Direct flights average 3h 5m

Connecting flights are more common

Frontier Airlines offers direct deals

Deals are frequent on 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

Oct 31

Dec 01

Dec 04

Jan 24

Jan 24

Jan 24

Jan 24

Feb 25

Feb 20

Oct 27

Dec 03

Dec 10

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 below the typical level

October offers the lowest median price

Direct flights average 3h 5m

Connecting flights are more common

Frontier Airlines offers direct deals

Deals are frequent on 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

Oct 31

Dec 01

Dec 04

Jan 24

Jan 24

Jan 24

Jan 24

Feb 25

Feb 20

Oct 27

Dec 03

Dec 10

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?