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

Across the trailing quarter, approximately 26.4% of flights from Fort Myers to Chicago have been non-stop. For flights that include stopovers, travelers typically encounter a median of 2 stopovers. 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 median duration of 3 hours and 23 minutes. For flights with one stop, the median travel time increases to 7 hours and 15 minutes. The route covers a distance of 1782 kilometers. Travelers should account for these differences when planning their journey.

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

Yes, setting a price alert for flights from Fort Myers to Chicago is advisable. Historically, deals on this route have been frequent. This suggests that prices can fluctuate, and an alert can help you capture a favorable fare. Monitoring prices for this route is a good strategy to secure a competitive offer.

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 today

459 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 7, 2026.)

Today’s best flight deals from Fort Myers to Chicago

Explore current cheapest deals departing from Fort Myers to Chicago

2026-12-04 – 2026-12-07
FMY - Chicago
49% AI deal score
$184
$163
Round trip
2026-12-03 – 2026-12-10
FMY - Chicago
46% AI deal score
$177
$182
Round trip
2026-12-03 – 2026-12-06
FMY - Chicago
46% AI deal score
$182
$187
Round trip
2026-12-03 – 2026-12-13
FMY - Chicago
45% AI deal score
$164
$187
Round trip
2026-12-10 – 2026-12-13
FMY - Chicago
45% AI deal score
$186
$196
Round trip
2026-12-06 – 2026-12-13
FMY - Chicago
45% AI deal score
$179
$197
Round trip
2026-12-06 – 2026-12-10
FMY - Chicago
45% AI deal score
$184
$197
Round trip
2026-11-24 – 2026-12-10
FMY - Chicago
44% AI deal score
$148
$207
Round trip
2026-11-24 – 2026-12-13
FMY - Chicago
44% AI deal score
$145
$207
Round trip
2026-11-24 – 2026-12-06
FMY - Chicago
44% AI deal score
$150
$207
Round trip

Fort Myers to Chicago: Overview

Insights for flights from Fort Myers to Chicago

Fares for cheap 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. Only 3% of recent fares from Fort Myers to Chicago were classified as a good price, indicating that finding a significant discount can be challenging.

When is the cheapest time to fly from Fort Myers to Chicago? The most affordable months to fly are generally April, with a median fare of $271, and September, where the median fare is $279. May also offers competitive pricing, with a median of $314.

A typical journey from Fort Myers to Chicago takes about 3h 23m, including connections. Most itineraries connect at least once, with the median number of stopovers for connecting flights being 2. This route covers a distance of 1782 kilometers, classifying it as a medium-haul flight.

How much is a round trip from Fort Myers to Chicago

Regular price: $141 - $335

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

Regularly, flights from Fort Myers to Chicago range from $141 to $335. The current lowest price is $163 with Frontier Airlines for travel from Dec 4-Dec 7.

now $163

Low $141

High $335

The cheapest time to fly from Fort Myers to Chicago

The cheapest month to fly from FMY to CHI 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, Sep 7

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (MDW)

$536

$535

One-way

Tue, Sep 8

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

$490

$487

One-way

Thu, Sep 10

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (MDW)

$522

$477

One-way

Wed, Sep 23

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

United Airlines

$174

$297

One-way

Fri, Sep 25

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (MDW)

Breeze Airways

$318

$329

One-way

Fri, Sep 25

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

American Airlines

$164

$339

One-way

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

2 nights

Sep 10 - Sep 12

$522 → $477

3 nights

Dec 4 - Dec 7

$184 → $163

11%

3 nights

Sep 8 - Sep 11

$490 → $487

3 nights

Sep 7 - Sep 10

$536 → $535

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

April is historically the cheapest month to fly.

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

⏱️ Flight duration

Direct flights take 3h 23m.

The median flight time for direct flights from Fort Myers to Chicago is 3h 23m.

✈️ Airlines & availability

Connecting flights are more common.

Historically, 26.4% of flights are direct, with connecting flights being more common.

🏆 Airline highlight

Frontier Airlines offers direct flights.

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

🎯 Booking tip

Deals appear frequently on this route.

Deals for flights from Fort Myers to Chicago appear frequently, about every 30 days.

Fort Myers main airports to depart from

Southwest Florida International (RSW)

Cheapest

Southwest Florida International Airport offers flights from Fort Myers to Chicago.

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

💸 Flights from ~$155

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering many connections to Chicago from Fort Myers.

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

💸 Flights from ~$155

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

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 usually results in higher prices, averaging $596. Even booking 7-13 days out sees prices climb to an average of $643, making the 14-27 day window the most economical choice based on past trends.

A flight from Fort Myers to Chicago is considered a good deal if it is priced at or below $295. The median price for this route across the trailing 90 days has been $426. Prices historically tend to increase significantly, with 75% of deals being $671 or more. Therefore, aiming for prices under $295 offers substantial savings.

Historically, April and September have offered the most affordable flights from Fort Myers to Chicago, with median prices of $271 and $279 respectively. May also presents a good option with a median price of $314. These months are typically less expensive than the annual median price for this route, which stands at $426, offering travelers better value.

Related routes

More routes from Fort Myers

Flights from Fort Myers to Colombo Flights from Fort Myers to Copenhagen Flights from Fort Myers to Dublin Flights from Fort Myers to Edinburgh Flights from Fort Myers to Frankfurt Flights from Fort Myers to Guadalajara Flights from Fort Myers to Istanbul Flights from Fort Myers to Las Vegas Flights from Fort Myers to Madrid Flights from Fort Myers to Milan Flights from Fort Myers to Myrtle Beach Flights from Fort Myers to Paris

Flights to Chicago from other cities

Flights from Frankfurt to Chicago Flights from Grand Rapids to Chicago Flights from Guadalajara to Chicago Flights from Hong Kong to Chicago Flights from Houston to Chicago Flights from Hyderabad to Chicago Flights from Indianapolis to Chicago Flights from Istanbul to Chicago Flights from Jacksonville to Chicago Flights from Johannesburg to Chicago Flights from Las Vegas to Chicago Flights from Wichita 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

Regular price: $141 - $335

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

Regularly, flights from Fort Myers to Chicago range from $141 to $335. The current lowest price is $163 with Frontier Airlines for travel from Dec 4-Dec 7.

now $163

Low $141

High $335

The cheapest time to fly from Fort Myers to Chicago

The cheapest month to fly from FMY to CHI 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, Sep 7

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (MDW)

$536

$535

One-way

Tue, Sep 8

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

$490

$487

One-way

Thu, Sep 10

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (MDW)

$522

$477

One-way

Wed, Sep 23

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

United Airlines

$174

$297

One-way

Fri, Sep 25

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (MDW)

Breeze Airways

$318

$329

One-way

Fri, Sep 25

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

American Airlines

$164

$339

One-way

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

2 nights

Sep 10 - Sep 12

$522 → $477

3 nights

Dec 4 - Dec 7

$184 → $163

11%

3 nights

Sep 8 - Sep 11

$490 → $487

3 nights

Sep 7 - Sep 10

$536 → $535

Popular Airports to fly from Fort Myers to Chicago