Find Cheap Flights from Fort Myers to Chicago (FMY - CHI)

Flights overview

Useful information for finding cheap flights from Fort Myers to Chicago and booking your next trip

Cheapest round-trip flights	$295	Southwest Nonstop 3 hr Thu, Jun 4 — Mon, Jun 8	The cheapest round-trip flight from Fort Myers to Chicago is currently $295
Cheapest one-way flight	$146	Southwest Nonstop 3 hr Wed, Jun 3	The cheapest one-way flight from Fort Myers to Chicago is currently $146
Last-minute weekend getaway	$324	Frontier Nonstop 4 hr Sat, May 9 — Sun, May 10	The cheapest last-minute weekend getaway from Fort Myers to Chicago is currently $324
Cheapest business class flights	$709	American Nonstop 4 hr Sat, Jun 6 — Mon, Jun 8	The cheapest business class round-trip flight from Fort Myers to Chicago is currently $709

Fastest flight	2 hr 45 min	The fastest nonstop flight from Fort Myers to Chicago takes 2 hr 45 min
Nonstop flights	Every day	There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Fort Myers to Chicago is typically February. The most expensive month to fly is typically May.

February Cheapest	Typical prices: $65–180
May Most expensive	Typical prices: $155–345

Popular airlines from Fort Myers to Chicago

Southwest

Nonstop

from $295

Typical price: $205–435

26 weekly nonstop flights

RSW - MDW, ORD Every day

2039 weekly connecting flights

RSW - MDW, ORD Every day
United

Nonstop

from $295

Typical price: $185–440

28 weekly nonstop flights

RSW - ORD Every day

274 weekly connecting flights

RSW - ORD Every day
American

Nonstop

from $295

Typical price: $185–465

21 weekly nonstop flights

RSW - ORD Every day

422 weekly connecting flights

RSW - ORD Every day
Delta

from $315

Typical price: $225–560

869 weekly connecting flights

RSW - MDW, ORD Every day
Frontier

Nonstop

from $324

Typical price: $150–530

2 weekly nonstop flights

RSW - ORD Every Sat, Sun

4 weekly connecting flights

RSW - MDW, ORD Every Mon, Thu, Sat
JetBlue

from $533

Typical price: $335–940

21 weekly connecting flights

RSW - ORD Every day

Popular airports near Fort Myers

Southwest Florida International Airport (RSW)

Fort Myers United States 22 min 9 mi
Punta Gorda Airport (PGD)

Punta Gorda United States 35 min 21 mi
Miami International Airport (MIA)

Miami United States 2 hr 17 min 113 mi
Fort Lauderdale-Hollywood International Airport (FLL)

Fort Lauderdale United States 2 hr 6 min 112 mi

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 26 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 25 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 23 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from Fort Myers to Chicago

The cheapest flights from Fort Myers to Chicago are usually in February. Typical ticket prices in February range from $65 to $180.

The cheapest round-trip flight from Fort Myers to Chicago recently found on Google Flights was with Southwest from $295. The cheapest one-way flight was with Southwest from $146.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Fort Myers to Chicago is $295, flying from Jul 16 to Jul 20.
The cheapest United flight from Fort Myers to Chicago is $295, flying from Jun 4 to Jun 8.
The cheapest American flight from Fort Myers to Chicago is $295, flying from Jun 4 to Jun 8.
The cheapest Delta flight from Fort Myers to Chicago is $315, flying from Jul 9 to Jul 13.
The cheapest Frontier flight from Fort Myers to Chicago is $324, flying from May 9 to May 10.
The cheapest JetBlue flight from Fort Myers to Chicago is $533, flying from Jul 24 to Jul 27.

The cheapest round-trip flight from Fort Myers to Chicago starts at $295 from Thu, Jun 4 to Mon, Jun 8. The cheapest one-way flight starts at $146 and departs on Wed, Jun 3.

2 hr 45 min is the shortest flight time from Fort Myers to Chicago.

Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.

It's easy to use Google Flights to find the cheapest days to fly from Fort Myers to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.

What counts as the best airline for your flights from Fort Myers to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Fort Myers to Chicago.

In terms of nonstop flights, United is the most popular. United offers 28 nonstop flights and 274 connecting flights per week. United flies from Southwest Florida International Airport (RSW) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Southwest is the most popular. Southwest offers 26 nonstop flights and 2,039 connecting flights per week. Southwest flies from Southwest Florida International Airport (RSW) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Fort Myers to Chicago are:

American offers 21 nonstop flights and 422 connecting flights per week. American flies from Southwest Florida International Airport (RSW) to Chicago O'Hare International Airport (ORD) .
Delta offers 869 connecting flights per week. Delta flies from Southwest Florida International Airport (RSW) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
Frontier offers 2 nonstop flights and 4 connecting flights per week. Frontier flies from Southwest Florida International Airport (RSW) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
JetBlue offers 21 connecting flights per week. JetBlue flies from Southwest Florida International Airport (RSW) to Chicago O'Hare International Airport (ORD) .

The number of connecting flights refers to distinct flights with at least one stop between Fort Myers and Chicago.

The cheapest round-trip flight from Fort Myers to Chicago recently found on Google Flights was with Southwest from $295. The cheapest one-way flight was with Southwest from $146.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Fort Myers to Chicago is $295, flying from Jul 16 to Jul 20.
The cheapest United flight from Fort Myers to Chicago is $295, flying from Jun 4 to Jun 8.
The cheapest American flight from Fort Myers to Chicago is $295, flying from Jun 4 to Jun 8.
The cheapest Delta flight from Fort Myers to Chicago is $315, flying from Jul 9 to Jul 13.
The cheapest Frontier flight from Fort Myers to Chicago is $324, flying from May 9 to May 10.
The cheapest JetBlue flight from Fort Myers to Chicago is $533, flying from Jul 24 to Jul 27.

Southwest, United, American and Frontier fly direct from Fort Myers to Chicago.

There are 26 Southwest direct flights from Fort Myers to Chicago per week. Flights are available every day.
There are 28 United direct flights from Fort Myers to Chicago per week. Flights are available every day.
There are 21 American direct flights from Fort Myers to Chicago per week. Flights are available every day.
There are 2 Frontier direct flights from Fort Myers to Chicago per week. Flights are available on Saturday and Sunday.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

The cheapest last-minute deal between Fort Myers and Chicago at price $324 is offered by Frontier from Sat, May 9 to Sun, May 10.

Southwest, United, American and Frontier fly direct from Fort Myers to Chicago.

There are 26 Southwest direct flights from Fort Myers to Chicago per week. Flights are available every day.
There are 28 United direct flights from Fort Myers to Chicago per week. Flights are available every day.
There are 21 American direct flights from Fort Myers to Chicago per week. Flights are available every day.
There are 2 Frontier direct flights from Fort Myers to Chicago per week. Flights are available on Saturday and Sunday.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

There are direct flights from Fort Myers to Chicago on a daily basis.

The cheapest direct (nonstop) round-trip flights between Fort Myers and Chicago start at $295 from Thu, Jun 4 to Mon, Jun 8 with Southwest.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Fort Myers to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.

The cheapest business class round-trip flights between Fort Myers and Chicago start at $709 from Sat, Jun 6 to Mon, Jun 8 with American.

The cheapest economy class round-trip flights between Fort Myers and Chicago start at $295 from Thu, Jun 4 to Mon, Jun 8.

To book business class trips from Fort Myers to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.

The best last-minute getaway deal for the next weekend between Fort Myers and Chicago starts at $324 from Sat, May 9 to Sun, May 10 with Frontier.

The cheapest last-minute deal between Fort Myers and Chicago at price $324 is offered by Frontier from Sat, May 9 to Sun, May 10.

To find last-minute flight deals from Fort Myers to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.