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 journeys involving connecting flights, travelers typically encounter a median of 2 stopovers. This indicates that while direct options exist, a significant portion of flights 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 median duration of 3 hours and 6 minutes. This route covers a distance of 1806 kilometers. For flights that include one stop, the median travel time increases significantly to 10 hours and 27 minutes. Travelers should consider these differences in duration when planning their journey.

How often do Chicago to Fort Myers flight prices drop?

Historically, flight prices for the Chicago to Fort Myers route have shown frequent drops. This suggests that travelers may often find opportunities for price reductions when monitoring this specific route. The frequent classification indicates that price fluctuations are common, potentially offering chances to book at a lower cost.

Flights From Chicago

To Fort Myers

Cheap Flights from Chicago to Fort Myers

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Deals from

Chicago

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

Prices updated 2 days ago

405 airlines compared

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

Today’s best flight deals from Chicago to Fort Myers

Explore current cheapest deals departing from Chicago to Fort Myers

2026-12-04 – 2026-12-07
CHI - Fort Myers
82% AI deal score
$612
$255
Round trip
2026-09-24 – 2026-09-28
CHI - Fort Myers
45% AI deal score
$166
$273
Round trip
2026-10-28 – 2026-10-31
CHI - Fort Myers
47% AI deal score
$258
$273
Round trip
2026-11-12 – 2026-11-16
CHI - Fort Myers
50% AI deal score
$195
$273
Round trip
2026-12-08 – 2026-12-15
CHI - Fort Myers
84% AI deal score
$598
$273
Round trip
2026-08-18 – 2026-08-25
CHI - Fort Myers
49% AI deal score
$199
$274
Round trip
2026-08-22 – 2026-08-29
CHI - Fort Myers
46% AI deal score
$188
$274
Round trip
2026-08-19 – 2026-08-25
CHI - Fort Myers
46% AI deal score
$190
$274
Round trip
2026-08-13 – 2026-08-19
CHI - Fort Myers
49% AI deal score
$198
$274
Round trip
2026-08-13 – 2026-08-20
CHI - Fort Myers
49% AI deal score
$197
$274
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 may require careful planning.

The cheapest time to fly from Chicago to Fort Myers is during the spring and summer months. April stands out as the most affordable month, with a median fare of $131. Following closely, May offers a median fare of $148, while July presents another cost-effective option with a median fare of $193.

A typical journey from Chicago to Fort Myers takes about 3h 6m. This route is classified as a medium-haul flight, covering a distance of 1806 kilometers. While direct flights from Chicago to Fort Myers are available, most itineraries connect at least once, with a median of 2 stopovers when connecting. New deals for this route appear almost daily, suggesting frequent opportunities to find suitable flights.

How much is a round trip from Chicago to Fort Myers

Regular price: $400 - $1,140

Prices are currently below the regular range.

The regular price range for flights from Chicago to Fort Myers is $400 to $1140. The current lowest deal is $255 with Frontier Airlines for travel from Dec 4-Dec 7.

now $255

Low $400

High $1,140

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

Southwest Airlines

Last-minute flights going from Chicago to Fort Myers

Thu, Aug 13

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

American Airlines

$198

$274

One-way

Thu, Aug 13

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

American Airlines

$197

$274

One-way

Thu, Aug 13

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

Southwest Airlines

$347

$284

One-way

Sat, Aug 15

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

$206

$275

One-way

Sat, Aug 15

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

$204

$275

One-way

Sat, Aug 15

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

Southwest Airlines

$334

$284

One-way

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

6 nights

Dec 20 - Dec 26

$839 → $354

58%

6 nights

Dec 22 - Dec 28

$838 → $383

54%

3 nights

Dec 25 - Dec 28

$861 → $423

51%

3 nights

Dec 12 - Dec 15

$637 → $274

57%

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 are above the typical level for Chicago to Fort Myers, with a median price of $959.

📅 Best time to fly

Fly in May for the best prices

Historically, May has offered the lowest median price at $167, making it the cheapest month to fly.

⏱️ Flight duration

Direct flights average 3h 6m

The typical direct flight from Chicago to Fort Myers takes 3 hours and 6 minutes.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 68.5% of recent routes, with a median of 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers a recent deal

A recent deal from Frontier Airlines was found for $255 via skyscanner, departing December 4.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Chicago to Fort Myers are frequently available, so check often.

Chicago main airports to depart from

Chicago Midway International (MDW)

Cheapest

Chicago Midway International offers a convenient departure point for flights to Fort Myers, often with competitive pricing.

📍 ~14 km from Chicago city center (reachable by car or public transport)

💸 Flights from ~$188

Fort Myers main airports to arrive at

Southwest Florida International (RSW)

Cheapest

Southwest Florida International 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 ~$93

Business & First Class Flight Deals to Fort Myers

80% AI deal score

$1,195

$823

Save $372

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 for a ticket has been observed at around $342. In contrast, purchasing tickets 0-6 days out typically sees average prices rise to $893, while booking 60+ days in advance can result in an average price of $1038. Planning your purchase within the recommended 14-27 day period can lead to significant savings.

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 has been $959. Prices can vary, with 75% of observed fares being $1424 or less. Aiming for a price at or below the good price threshold of $489 can help travelers secure a more economical fare.

Historically, the cheapest months to fly from Chicago to Fort Myers have been April, May, and July. In April, the median price was $131, while in May it was $148. July also presented a median price of $193, making it one of the more affordable options. The annual median price for this route has been $959, indicating that these months offer considerably lower fares compared to the yearly average.

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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: $400 - $1,140

Prices are currently below the regular range.

The regular price range for flights from Chicago to Fort Myers is $400 to $1140. The current lowest deal is $255 with Frontier Airlines for travel from Dec 4-Dec 7.

now $255

Low $400

High $1,140

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

Southwest Airlines

Last-minute flights going from Chicago to Fort Myers

Thu, Aug 13

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

American Airlines

$198

$274

One-way

Thu, Aug 13

⌛ Last-Minute

ORD - Fort Myers

Chicago (ORD) - Fort Myers (RSW)

American Airlines

$197

$274

One-way

Thu, Aug 13

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

Southwest Airlines

$347

$284

One-way

Sat, Aug 15

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

$206

$275

One-way

Sat, Aug 15

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

$204

$275

One-way

Sat, Aug 15

⌛ Last-Minute

MDW - Fort Myers

Chicago (MDW) - Fort Myers (RSW)

Southwest Airlines

$334

$284

One-way

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

6 nights

Dec 20 - Dec 26

$839 → $354

58%

6 nights

Dec 22 - Dec 28

$838 → $383

54%

3 nights

Dec 25 - Dec 28

$861 → $423

51%

3 nights

Dec 12 - Dec 15

$637 → $274

57%

Popular Airports to fly from Chicago to Fort Myers