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

Across the trailing quarter, approximately 21.7% of flights from Fort Myers to Chicago were non-stop. For travelers who opt for connecting flights, the median number of stopovers observed was 2. This indicates that while direct options are available, a significant portion of routes involve at least one connection.

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 21 minutes, covering a distance of 1782 kilometers. For flights that include one stop, the median travel time increases significantly to 8 hours and 30 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?

Given that deals for flights from Fort Myers to Chicago are classified as frequent, setting a price alert is a recommended strategy. Historically, this route has shown consistent price fluctuations, making it beneficial to monitor prices over time. An alert can help you identify when prices drop to a more favorable rate within a 30-day window.

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 4 days ago

476 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 12, 2026.)

Today’s best flight deals from Fort Myers to Chicago

Explore current cheapest deals departing from Fort Myers to Chicago

2027-01-16 – 2027-01-19
FMY - Chicago
66% AI deal score
$148
$124
Round trip
2027-01-16 – 2027-01-27
FMY - Chicago
48% AI deal score
$134
$128
Round trip
2027-01-16 – 2027-01-25
FMY - Chicago
49% AI deal score
$142
$128
Round trip
2027-01-13 – 2027-01-19
FMY - Chicago
65% AI deal score
$146
$128
Round trip
2027-01-13 – 2027-01-25
FMY - Chicago
47% AI deal score
$133
$128
Round trip
2027-01-16 – 2027-01-28
FMY - Chicago
48% AI deal score
$134
$128
Round trip
2027-01-16 – 2027-02-01
FMY - Chicago
47% AI deal score
$132
$128
Round trip
2027-01-11 – 2027-01-19
FMY - Chicago
49% AI deal score
$142
$128
Round trip
2027-01-13 – 2027-01-16
FMY - Chicago
65% AI deal score
$147
$128
Round trip
2027-01-16 – 2027-01-20
FMY - Chicago
65% AI deal score
$148
$128
Round trip

Fort Myers to Chicago: Overview

Insights for flights from Fort Myers to Chicago

A typical journey from Fort Myers to Chicago takes about 3h 21m, including connections. This route covers a distance of 1782 kilometers, classifying it as a medium-haul flight. Most itineraries on this route involve at least one connection.

For travelers seeking cheap flights from Fort Myers to Chicago, fares typically range from $373–$1119, with a median of $631. Right now, current fares are below the typical level, and only 4% of recent fares were classified as a good price. New deals appear almost daily for this route, suggesting frequent opportunities to find better prices.

When is the cheapest time to fly from Fort Myers to Chicago? The most affordable month to fly is November, with a median fare of $327. Following closely is July, where the median fare is $385. January also offers relatively lower prices, with a median fare of $565.

Most itineraries for flights from Fort Myers to Chicago connect at least once, with only 21.7% of recent fares being non-stop. For connecting flights, the typical number of connections is 2, which significantly extends the overall journey time compared to direct options.

How much is a round trip from Fort Myers to Chicago

Regular price: $112 - $353

Prices are within the regular range.

The regular price range for flights from Fort Myers to Chicago is $112 to $353. The current lowest deal is $126 with Frontier Airlines for travel from Nov 24-Dec 13.

now $126

Low $112

High $353

The cheapest time to fly from Fort Myers to Chicago

The cheapest month to fly from Fort Myers to Chicago is November, with a median price of $330. The most expensive month is October, with a median price of $820. Prices are generally lower from January to December.

November

Cheapest

Flights from $330

October

Most Expensive

Flights from $820

Jan

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Fort Myers to Chicago

Frontier Airlines

Last-minute flights going from Fort Myers to Chicago

Wed, Oct 28

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

American Airlines

$167

$218

One-way

Tue, Nov 3

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

United Airlines

$157

$218

One-way

Wed, Nov 4

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

United Airlines

$157

$218

One-way

Thu, Nov 5

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

United Airlines

$157

$218

One-way

Thu, Nov 5

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

American Airlines

$162

$219

One-way

Thu, Nov 12

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

United Airlines

$246

$253

One-way

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

4 nights

Dec 10 - Dec 14

$174 → $139

20%

3 nights

Dec 10 - Dec 13

$174 → $145

17%

3 nights

Dec 3 - Dec 6

$174 → $150

14%

7 nights

Dec 3 - Dec 10

$167 → $148

11%

Popular Airports to fly from Fort Myers to Chicago

Fort Myers - Chicago route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Fort Myers to Chicago are below the typical level for this route.

📅 Best time to fly

November is historically cheapest at $327.

Historically, November is the cheapest month to fly, with a median price of $327.

⏱️ Flight duration

Direct flights average 3h 21m.

Direct flights from Fort Myers to Chicago typically take 3 hours and 21 minutes.

✈️ Airlines & availability

Connecting flights are dominant.

Connecting flights are dominant on this route, with a median of 2 stopovers.

🏆 Airline highlight

Frontier Airlines has a deal for $126.

Frontier Airlines offers a deal for $126 from Fort Myers to Chicago.

🎯 Booking tip

Deals appear frequently.

Deals on flights from Fort Myers to Chicago appear frequently, so check often.

Fort Myers main airports to depart from

Southwest Florida International (RSW)

Cheapest

Southwest Florida International is a good option for flights from Fort Myers to Chicago.

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

💸 Flights from ~$124

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 city center (reachable by car, train, bus)

💸 Flights from ~$124

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

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

💸 Flights from ~$198

Business & First Class Flight Deals to Chicago

$979

Save $516

From RSW

Elite

Oct 07

Chicago, United States

77% AI deal score

$1,688

$1,069

Save $619

From RSW

Elite

Oct 21

Chicago, United States

74% AI deal score

$1,196

$912

Save $284

From RSW

Chicago, United States

69% AI deal score

$870

$797

Save $73

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the sweet spot for booking flights from Fort Myers to Chicago to secure the lowest prices is typically between 28 and 59 days before departure. During this period, the average price observed was $1350. Booking within 14-27 days of departure also showed favorable pricing, with an average of $1446. Prices tend to be higher for very last-minute bookings, with flights booked 0-6 days out averaging around $2676.

A flight from Fort Myers to Chicago is generally considered a good deal if it is priced at or below $373. This threshold represents the lowest 25% of prices observed across the trailing quarter. The median price for this route historically stands at $631, while prices in the higher range can go up to $1119 or more.

Historically, November has been the most affordable month to fly from Fort Myers to Chicago, with a median price of $327. July also offers competitive pricing, with a median of $385. While January is listed among the cheapest months with a median of $565, it also represents the most expensive month on an annual basis, with the same median price. The overall annual median price for this route is $631.

Related routes

More routes from Fort Myers

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 from Fort Myers to Philadelphia

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: $112 - $353

Prices are within the regular range.

The regular price range for flights from Fort Myers to Chicago is $112 to $353. The current lowest deal is $126 with Frontier Airlines for travel from Nov 24-Dec 13.

now $126

Low $112

High $353

The cheapest time to fly from Fort Myers to Chicago

November

Cheapest

Flights from $330

October

Most Expensive

Flights from $820

Jan

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Fort Myers to Chicago

Frontier Airlines

Last-minute flights going from Fort Myers to Chicago

Wed, Oct 28

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

American Airlines

$167

$218

One-way

Tue, Nov 3

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

United Airlines

$157

$218

One-way

Wed, Nov 4

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

United Airlines

$157

$218

One-way

Thu, Nov 5

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

United Airlines

$157

$218

One-way

Thu, Nov 5

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

American Airlines

$162

$219

One-way

Thu, Nov 12

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

United Airlines

$246

$253

One-way

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

4 nights

Dec 10 - Dec 14

$174 → $139

20%

3 nights

Dec 10 - Dec 13

$174 → $145

17%

3 nights

Dec 3 - Dec 6

$174 → $150

14%

7 nights

Dec 3 - Dec 10

$167 → $148

11%

Popular Airports to fly from Fort Myers to Chicago