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

In the trailing 90 days, approximately 26.4% of flights from Fort Myers to Chicago were non-stop. For flights that include stopovers, the median number of stopovers observed was 2. This indicates that while direct options are available, a significant portion of flights on this route involve at least one connection. Travelers should consider this when planning their journey and evaluating travel time.

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 flight time is considerably longer, averaging 7 hours and 15 minutes. This difference highlights the convenience of direct flights for this route. Travelers should account for these durations when planning their itinerary.

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

Based on historical data from the trailing 30 days, deals for flights from Fort Myers to Chicago are classified as frequent. This suggests that price fluctuations and opportunities for good deals occur regularly on this route. Setting a price alert could be beneficial for travelers looking to secure a favorable fare, as new deals tend to appear often. Monitoring prices can help identify opportune booking moments.

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

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Prices updated 5 days ago

402 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Jul 12, 2026.)

Today’s best flight deals from Fort Myers to Chicago

Explore current cheapest deals departing from Fort Myers to Chicago

Round trip

Sort by: Cheapest

August 10 - August 15

Cheapest

RSW - Chicago

$198

$188

Round trip

August 19 - August 22

Cheapest

RSW - Chicago

$195

$188

Round trip

August 18 - August 25

Cheapest

RSW - Chicago

$183

$188

Round trip

August 26 - August 29

Cheapest

RSW - Chicago

$193

$188

Round trip

September 26 - September 29

Cheapest

RSW - Chicago

$170

$188

Round trip

September 5 - September 7

Cheapest

RSW - Chicago

$167

$188

Round trip

August 5 - August 8

Best

Earliest

RSW - Chicago

$205

$189

Round trip

August 13 - August 15

RSW - Chicago

$202

$189

Round trip

August 20 - August 25

RSW - Chicago

$193

$189

Round trip

August 6 - August 10

Best

RSW - Chicago

$205

$189

Round trip

Unlock all 500+ flight deals to Chicago and get alerts when great deals appear

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–$671, with a median price of $426. Right now, current fares are above the typical level, and only 3% of recent fares were classified as a good price. New deals appear almost daily, suggesting frequent opportunities to find better prices.

When looking for cheap flights from Fort Myers to Chicago, the data indicates that April is the most affordable month to fly, with a median fare of $271. Following closely, September also offers competitive pricing, with a median fare of $279. May is another favorable month, showing a median fare of $314.

The typical journey time for flights from Fort Myers to Chicago is 3h 23m. However, only 26.4% of recent itineraries are non-stop, meaning most itineraries connect at least once. For connecting flights, 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 typically involves a flight duration that balances direct travel with the potential for connecting itineraries.

How much is a round trip from Fort Myers to Chicago

Regular price: $151 - $422

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

The regular price range for this route is $151 to $422. The current lowest deal is $188 with American Airlines, for travel from Aug 10-Aug 15.

now $188

Low $151

High $422

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

American Airlines

Southwest Airlines

Last-minute flights going from Fort Myers to Chicago

Sat, Jul 11

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

American Airlines

$964

$536

One-way

Wed, Jul 15

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

American Airlines

$736

$473

One-way

Mon, Jul 20

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

Avelo Airlines

$776

$465

One-way

Mon, Jul 20

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

Avelo Airlines

$776

$517

One-way

Tue, Jul 21

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

United Airlines

$635

$431

One-way

Wed, Jul 22

⌛ Last-Minute

RSW - Chicago

Fort Myers (RSW) - Chicago (ORD)

Avelo Airlines

$708

$428

One-way

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

2 nights

Jul 4 - Jul 6

$960 → $465

52%

1 night

Jul 4 - Jul 5

$964 → $475

51%

1 night

Jul 7 - Jul 8

$958 → $473

51%

3 nights

Jul 8 - Jul 11

$945 → $473

50%

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 at $188.

📅 Best time to fly

Fly in March for the cheapest prices.

Historically, March is the cheapest month to fly, with a median price of $148.

⏱️ Flight duration

Direct flights take 3h 23m.

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

✈️ Airlines & availability

Connecting flights are dominant.

26.4% of recent flights from Fort Myers to Chicago are direct, with 2 stopovers typical.

🏆 Airline highlight

American Airlines offers a recent deal.

American Airlines recently offered a deal for $188 from Fort Myers to Chicago.

🎯 Booking tip

Deals are frequent on this route.

Deals on flights from Fort Myers to Chicago are frequent, appearing within 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 departure option from Fort Myers.

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

💸 Flights from ~$188

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

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

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

💸 Flights from ~$188

Chicago Rockford International (RFD)

Chicago Rockford International Airport offers an alternative arrival option for your trip to Chicago.

📍 ~126 km from Chicago city center (reachable by car)

💸 Flights from ~$346

O Hare International (ORD)

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

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

💸 Flights from ~$188

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, train)

💸 Flights from ~$282

Gerald R. Ford International (GRR)

Gerald R. Ford International is Michigan's second largest airport with a robust domestic network.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$223

Dane County Regional (MSN)

Dane County Regional is a reliable regional hub with efficient operations and good amenities.

📍 ~205 km from Chicago (reachable by car)

💸 Flights from ~$159

South Bend International (SBN)

Cheapest

South Bend International is the closest alternative airport to the Chicago metro area.

📍 ~120 km from Chicago (reachable by car, train)

💸 Flights from ~$139

Fort Wayne International (FWA)

Fort Wayne International offers multiple cabin classes and solid connectivity for eastern domestic destinations.

📍 ~235 km from Chicago (reachable by car)

💸 Flights from ~$278

Business & First Class Flight Deals to Chicago

65% AI deal score

$1,858

From RSW

Elite

Nov 19

Chicago, United States

65% AI deal score

$1,858

From RSW

Elite

Aug 03

Chicago, United States

50% AI deal score

Chicago, United States

49% AI deal score

$1,202

$1,127

Save $75

From RSW

Elite

Dec 04

Chicago, United States

49% AI deal score

Chicago, United States

49% AI deal score

$2,024

From RSW

Elite

Oct 15

Chicago, United States

49% AI deal score

$2,024

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 around $392. Booking within 0-6 days of departure typically sees prices rise to an average of $596. Even booking 7-13 days out can result in higher prices, averaging $643. For the trailing 90 days, prices generally increase the closer you get to the departure date, with the exception of the 14-27 day window.

Across the trailing quarter, 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 over the same 90-day period was $426. Prices above $671 are typically in the more expensive range. Keeping an eye out for fares at or below the $295 threshold can help travelers secure a favorable price.

Historically, April and September have been the cheapest months to fly from Fort Myers to Chicago, with median prices of $271 and $279, respectively. May also offers competitive prices, with a median of $314. The annual median price for this route is $426. Travelers looking for more affordable options should consider these months for their journeys.

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