How many flights from Fort Myers to Chicago are non-stop?

Based on data from the trailing 90 days, approximately 26.4% of flights from Fort Myers to Chicago are non-stop. For flights that do include stopovers, the median number of stopovers is typically two. This indicates that while direct options are available, a significant portion of routes involve connections.

What's the flight time from Fort Myers to Chicago?

The typical direct flight from Fort Myers to Chicago has a duration of 3 hours and 23 minutes, covering a distance of 1782 kilometers. For flights with one stop, the median travel time increases significantly to 7 hours and 15 minutes. This difference highlights the convenience of non-stop options for this route.

Should I set a price alert for Fort Myers to Chicago flights?

Yes, setting a price alert for Fort Myers to Chicago flights is advisable. Historically, deals on this route are classified as frequent, indicating that prices fluctuate regularly. This frequency of price changes, observed over a 30-day period, suggests that alerts can help you capture better fares as they become available. Monitoring prices can lead to potential savings on your travel.

Flights From Fort Myers

To Chicago

Cheap Flights from Fort Myers to Chicago

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

Deals from

Fort Myers

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

Prices updated 7 days ago

454 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 24, 2026.)

Today’s best flight deals from Fort Myers to Chicago

Explore current cheapest deals departing from Fort Myers to Chicago

2026-12-07 – 2026-12-13
FMY - Chicago
48% AI deal score
$194
$182
Round trip
2026-12-03 – 2026-12-06
FMY - Chicago
47% AI deal score
$193
$188
Round trip
2026-12-04 – 2026-12-06
FMY - Chicago
46% AI deal score
$194
$197
Round trip
2026-12-03 – 2026-12-14
FMY - Chicago
44% AI deal score
$172
$205
Round trip
2026-12-03 – 2026-12-07
FMY - Chicago
45% AI deal score
$193
$205
Round trip
2026-11-21 – 2026-12-06
FMY - Chicago
44% AI deal score
$157
$205
Round trip
2026-12-03 – 2026-12-10
FMY - Chicago
45% AI deal score
$188
$206
Round trip
2026-11-22 – 2026-12-06
FMY - Chicago
44% AI deal score
$160
$207
Round trip
2026-12-04 – 2026-12-07
FMY - Chicago
45% AI deal score
$193
$213
Round trip
2026-12-04 – 2026-12-14
FMY - Chicago
44% AI deal score
$174
$213
Round trip

Fort Myers to Chicago: Overview

Insights for flights from Fort Myers to Chicago

Fares for flights from Fort Myers to Chicago typically range from $295 to $671, with a median price of $426. Right now, current fares are above the typical level for this route, and only 3% of recent fares were classified as a good price. New deals appear almost daily, suggesting frequent opportunities to find better prices.

If you are looking for cheap flights from Fort Myers to Chicago, the data indicates that April is often the most affordable month to fly, with a median fare of $271. Following closely, September also presents a good value, with a median fare of $279. May is another favorable month, showing a median fare of $314.

A typical journey from Fort Myers to Chicago takes about 3h 23m, including connections. Most itineraries for this route connect at least once. For those connecting, the median number of stopovers is 2.

The distance between Fort Myers and Chicago is 1782 kilometers, classifying this as a medium-haul route. This distance means you can expect a flight that is neither very short nor extremely long, balancing travel time with the opportunity to reach a significant destination.

How much is a round trip from Fort Myers to Chicago

Regular price: $152 - $338

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

The regular price range for flights from Fort Myers to Chicago is between $152 and $338. The current lowest deal is $182 with Frontier Airlines for travel from Dec 7-Dec 13.

now $182

Low $152

High $338

The cheapest time to fly from Fort Myers to Chicago

The cheapest month to fly from Fort Myers to Chicago is March, with a median price of $148. The most expensive month is February, with a median price of $926. Prices are generally lower from March to November.

March

Cheapest

Flights from $148

February

Most Expensive

Flights from $926

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Fort Myers to Chicago

Frontier Airlines

Southwest Airlines

Last-minute flights going from Fort Myers to Chicago

Mon, Aug 31

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

$644

$487

One-way

Tue, Sep 1

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

Deutsche Luft Hansa

$496

One-way

Wed, Sep 2

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

$471

$424

One-way

Thu, Sep 3

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

$471

$472

One-way

Thu, Sep 3

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

$477

One-way

Fri, Sep 4

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (MDW)

Frontier Airlines

$512

$459

One-way

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

1 night

Aug 24 - Aug 25

$686 → $467

32%

1 night

Aug 26 - Aug 27

$623 → $476

24%

3 nights

Aug 28 - Aug 31

$640 → $515

20%

2 nights

Aug 29 - Aug 31

$589 → $477

19%

Popular Airports to fly from Fort Myers to Chicago

Fort Myers - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from Fort Myers to Chicago are above the typical level of $426.

📅 Best time to fly

Fly in April for the best prices

Historically, April is the cheapest month to fly, with a median price of $271.

⏱️ Flight duration

Direct flights average 3h 23m

The typical direct flight from Fort Myers to Chicago takes 3h 23m.

✈️ Airlines & availability

Connecting flights are more common

Historically, 26.4% of recent flights from Fort Myers to Chicago were direct.

🏆 Airline highlight

Frontier Airlines offers direct flights

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

🎯 Booking tip

Deals appear frequently

Deals on flights from Fort Myers to Chicago appear frequently, typically every 30 days.

Fort Myers main airports to depart from

Southwest Florida International (RSW)

Cheapest

Southwest Florida International Airport offers flights to Chicago, providing a convenient option for your journey.

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

💸 Flights from ~$188

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights from Fort Myers to Chicago.

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

💸 Flights from ~$237

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

📍 ~135 km from Chicago (reachable by car or train)

💸 Flights from ~$219

Business & First Class Flight Deals to Chicago

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

Elite

Best Elite deals to Chicago

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

From RSW

Elite

Oct 05

Chicago, United States

82% AI deal score

$1,485

$865

Save $620

United Airlines

Business Class

From RSW

Elite

Sep 25

Chicago, United States

81% AI deal score

$1,448

$879

Save $569

United Airlines

Business Class

From RSW

Elite

Sep 22

Chicago, United States

81% AI deal score

$1,498

$893

Save $605

United Airlines

Business Class

From RSW

Elite

Oct 02

Chicago, United States

79% AI deal score

$1,476

$824

Save $652

From RSW

Elite

Sep 29

Chicago, United States

78% AI deal score

$1,211

$875

Save $336

United Airlines

Business Class

From RSW

Elite

Oct 02

Chicago, United States

77% AI deal score

$1,458

$889

Save $569

From RSW

Chicago, United States

70% AI deal score

$1,028

$886

Save $142

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the best prices for flights from Fort Myers to Chicago are found when booking 14-27 days in advance. During this period, the average price is typically around $392. Booking within 0-6 days of departure generally sees prices rise to approximately $596, while booking 7-13 days out averages $643. Prices tend to be higher for bookings made further out, with flights booked 60+ days in advance averaging $511. This trend is based on pricing data observed over a 90-day period.

A good deal for a flight from Fort Myers to Chicago is considered to be around $295 or less. Historically, 25% of all observed prices for this route have been at or below this threshold. The median price for this route across the trailing 90 days was $426, while prices at the 75th percentile reached $671. These figures can help you gauge whether a particular fare is favorable.

Historically, the cheapest months to fly from Fort Myers to Chicago are April, September, and May. April typically sees a median price of $271, while September's median is $279. May also offers competitive pricing, with a median of $314. The annual median price for this route, based on data from the trailing 270 days, is $426, indicating that these months offer significant savings compared to the yearly average.

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More routes from Fort Myers

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Fort Myers to Chicago: Overview

Insights for flights from Fort Myers to Chicago

How much is a round trip from Fort Myers to Chicago

Regular price: $152 - $338

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

The regular price range for flights from Fort Myers to Chicago is between $152 and $338. The current lowest deal is $182 with Frontier Airlines for travel from Dec 7-Dec 13.

now $182

Low $152

High $338

The cheapest time to fly from Fort Myers to Chicago

March

Cheapest

Flights from $148

February

Most Expensive

Flights from $926

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Fort Myers to Chicago

Frontier Airlines

Southwest Airlines

Last-minute flights going from Fort Myers to Chicago

Mon, Aug 31

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

$644

$487

One-way

Tue, Sep 1

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

Deutsche Luft Hansa

$496

One-way

Wed, Sep 2

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

$471

$424

One-way

Thu, Sep 3

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

$471

$472

One-way

Thu, Sep 3

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

$477

One-way

Fri, Sep 4

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (MDW)

Frontier Airlines

$512

$459

One-way

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

1 night

Aug 24 - Aug 25

$686 → $467

32%

1 night

Aug 26 - Aug 27

$623 → $476

24%

3 nights

Aug 28 - Aug 31

$640 → $515

20%

2 nights

Aug 29 - Aug 31

$589 → $477

19%

Popular Airports to fly from Fort Myers to Chicago

Fort Myers - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from Fort Myers to Chicago are above the typical level of $426.

📅 Best time to fly

Fly in April for the best prices

Historically, April is the cheapest month to fly, with a median price of $271.

⏱️ Flight duration

Direct flights average 3h 23m

The typical direct flight from Fort Myers to Chicago takes 3h 23m.

✈️ Airlines & availability

Connecting flights are more common

Historically, 26.4% of recent flights from Fort Myers to Chicago were direct.

🏆 Airline highlight

Frontier Airlines offers direct flights

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

🎯 Booking tip

Deals appear frequently

Deals on flights from Fort Myers to Chicago appear frequently, typically every 30 days.

Fort Myers main airports to depart from

Southwest Florida International (RSW)

Cheapest

Southwest Florida International Airport offers flights to Chicago, providing a convenient option for your journey.

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

💸 Flights from ~$188

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights from Fort Myers to Chicago.

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

💸 Flights from ~$237

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

Chicago, United States

79% AI deal score

$1,476

$824

Save $652

From RSW

Elite

Sep 29

Chicago, United States

78% AI deal score

$1,211

$875

Save $336

United Airlines

Business Class

From RSW

Elite

Oct 02

Chicago, United States

77% AI deal score

$1,458

$889

Save $569

From RSW

Chicago, United States

70% AI deal score

$1,028

$886

Save $142

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Fort Myers to Chicago

Today’s best flight deals from Fort Myers to Chicago

Fort Myers to Chicago: Overview

Insights for flights from Fort Myers to Chicago

How much is a round trip from Fort Myers to Chicago

The cheapest time to fly from Fort Myers to Chicago

Direct flights from Fort Myers to Chicago

Last-minute flights going from Fort Myers to Chicago

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

Popular Airports to fly from Fort Myers to Chicago

Fort Myers - Chicago route insights

Recent fares are above the typical level

Fly in April for the best prices

Direct flights average 3h 23m

Connecting flights are more common

Frontier Airlines offers direct flights

Deals appear frequently

Fort Myers main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Oct 05

Sep 25

Sep 22

Oct 02

Sep 29

Oct 02

Feb 11

Feb 02

Dec 28

Dec 10

Sep 29

Oct 01

Frequently Asked Questions About Flights to Chicago

How early should I book Fort Myers to Chicago flights to get the cheapest price?

How do I know if a Fort Myers to Chicago flight is a good deal?

What's the best month to fly from Fort Myers to Chicago?

How many flights from Fort Myers to Chicago are non-stop?

What's the flight time from Fort Myers to Chicago?

Should I set a price alert for Fort Myers to Chicago flights?

Related routes

More routes from Fort Myers

Flights to Chicago from other cities

Fort Myers to Chicago: Overview

Insights for flights from Fort Myers to Chicago

How much is a round trip from Fort Myers to Chicago

The cheapest time to fly from Fort Myers to Chicago

Direct flights from Fort Myers to Chicago

Last-minute flights going from Fort Myers to Chicago

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

Popular Airports to fly from Fort Myers to Chicago

Fort Myers - Chicago route insights

Recent fares are above the typical level

Fly in April for the best prices

Direct flights average 3h 23m

Connecting flights are more common

Frontier Airlines offers direct flights

Deals appear frequently

Fort Myers main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Oct 05

Sep 25

Sep 22

Oct 02

Sep 29

Oct 02

Feb 11

Feb 02

Dec 28

Dec 10

Sep 29

Oct 01

Frequently Asked Questions About Flights to Chicago

How early should I book Fort Myers to Chicago flights to get the cheapest price?

How do I know if a Fort Myers to Chicago flight is a good deal?

What's the best month to fly from Fort Myers to Chicago?