Cheap Flight Tickets from Chicago (MDW) to Fort Myers (RSW), Starting at $395

Good to Know: Cheapest and Fastest MDW - RSW Flights

Useful information for finding best airline tickets from Chicago Midway International to Southwest Florida International on your next trip.

Cheapest Round Trip Flight

$698

WN Southwest Airlines • 1 stop • 16h 50m

Nov 21 – Nov 28

The cheapest round trip flight from Chicago to Fort Myers (MDW-RSW-MDW) is currently $698

🔍 Search Flights

Cheapest Direct Flight

$395

WN Southwest Airlines • nonstop • 4h

Oct 30

The cheapest nonstop flight from Chicago to Fort Myers (MDW-RSW) is currently $395

🔍 Search Flights

Fastest Flight

4h

The fastest nonstop flight from Chicago to Fort Myers (MDW-RSW) takes 4h

Top Airlines Flying from Chicago to Fort Myers

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Alaska Airlines -AS

Alaska Airlines

Latest Flight Deals from Chicago (MDW) to Fort Myers (RSW)

Compare and book low fare round-trip air tickets from Chicago to Fort Myers. Ideal for travelers with confirmed return itineraries.

Nov 21 - Nov 28, Economy
WN
Chicago → Fort Myers
16h 50m
9:30 PM - 8:40 AM • 1 stop
WN
Chicago → Fort Myers
20h 45m
7:05 PM - 6:50 AM • 2 stops
$698
Southwest Airlines
Nov 21 - Nov 28, Economy
WN
Chicago → Fort Myers
16h 45m
12:45 PM - 11:50 PM • 1 stop
WN
Chicago → Fort Myers
17h
3:05 PM - 12:25 AM • 1 stop
$743
Southwest Airlines
Nov 21 - Nov 28, Economy
WN
Chicago → Fort Myers
21h 45m
10:10 AM - 12:15 AM • 2 stops
WN
Chicago → Fort Myers
10h 5m
7:20 PM - 12:25 AM • 1 stop
$749
Southwest Airlines
Nov 21 - Nov 28, Economy
DL
Chicago → Fort Myers
15h 31m
12:30 PM - 11:01 PM • 1 stop
DL
Chicago → Fort Myers
12h 31m
6:00 AM - 12:51 PM • 1 stop
$797
Delta Airlines
Nov 21 - Nov 28, Economy
DL
Chicago → Fort Myers
18h 47m
10:34 AM - 11:01 PM • 1 stop
DL
Chicago → Fort Myers
12h 31m
6:00 AM - 12:51 PM • 1 stop
$797
Delta Airlines
Nov 21 - Nov 28, Economy
WN
Chicago → Fort Myers
15h 55m
10:10 AM - 9:05 PM • 1 stop
WN
Chicago → Fort Myers
20h 45m
7:05 PM - 6:50 AM • 2 stops
$798
Southwest Airlines

Fly from Chicago to Fort Myers with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Fort Myers? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to Fort Myers Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to RSW?
The most popular airline flying from Chicago to Fort Myers are
Can I fly from MDW to RSW non-stop?
Yes, you can fly MDW to RSW non-stop on
Which airlines fly nonstop between Chicago and Fort Myers?
The non-stop flights between Chicago and Fort Myers are .
What’s the earliest departure time from MDW to RSW Airport?
The earliest flight leaves MDW at 5:05 am and lands in RSW - Southwest Florida International
What are the airports in Fort Myers?
RSW
Can I make changes to my Chicago to Fort Myers flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from MDW to RSW?
Read the fare rules of the Chicago to Fort Myers air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and Fort Myers?
operate flights between Chicago and Fort Myers
How long does a flight from Chicago to Fort Myers take?
It takes approximately 3 hour to fly non-stop from MDW to RSW, which is 1105.1 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to Fort Myers (RSW) ?
In the past couple of days, the cheapest tickets to RSW from MDW were found on DL : USD 797
Do I need a passport to fly between MDW and RSW?
No
What’s the latest departure time from MDW to RSW ?
The last flight leaves MDW at 9:30 pm

Essential Information for Booking Flights from Chicago (MDW) - AI Insights

What's the cheapest airline from mdw to rsw?
You can find the cheapest flights from Chicago Midway International Airport (mdw) to Southwest Florida International Airport (rsw) with Southwest Airlines. For a round-trip economy flight with one stop, you can expect to pay around $200-$300. Booking in advance is recommended, as fares tend to decrease after 14 days. Look for Low Fares and Budget-friendly options on fareleaders.com for the best deals.
What's the popular airline to fly from mdw to rsw?
You can fly from Chicago Midway International Airport (mdw) to Southwest Florida International Airport (rsw) with Southwest Airlines (WN), which offers flights with one stop. It's recommended to book your flight at least 14 days in advance to get the best Low Fares. You can find the cheapest airfares on our website, which provides a comprehensive comparison of airfares from various airlines.
What's the cheapest day of the week to fly from mdw to rsw?
The cheapest day to fly from Chicago Midway International Airport (mdw) to Southwest Florida International Airport (rsw) is Sunday. Flying on Sundays can result in budget-friendly flights, making it a great option for travelers looking for affordable airfares. Low fares can be found on Sundays, especially during off-peak travel seasons like February or July.
What's the cheapest month to fly from mdw to rsw?
The cheapest month to fly from Chicago Midway International (mdw) to Southwest Florida International (rsw) is typically November or December, with average airfares for a Round Trip (return journey) economy ticket ranging from $150-$250. For a budget-friendly option, consider flying in July or October. Low Fares and Savings can be found with airlines offering competitive airfares.
Which airline/airlines fly from mdw to rsw?
The airlines that fly from Chicago Midway International Airport (mdw) to Southwest Florida International Airport (rsw) include Porter Airline (PD), American Airlines (AA), Southwest Airlines (WN), Allegiant (G4), JetBlue Airways (B6), United Airlines (UA), WestJet Airlines (WS), Air Transat (TS), Volaris Airline (Y4), and Delta Airlines (DL). You can find more information about these airlines and their flight schedules on their official websites. For budget-friendly flights, consider checking the websites of these airlines for the cheapest airfares.
What are the available flights from Chicago Midway International Airport (mdw) to Southwest Florida International Airport (rsw)?
You can find available flights from Chicago Midway International Airport (mdw) to Southwest Florida International Airport (rsw) on our website, which offers a comprehensive fare comparison for flights from Milwaukee to Southwest Florida International Airport (rsw) via other airlines.
How can I book a one-way ticket from Milwaukee to Southwest Florida International Airport (rsw)?
To book a one-way ticket from Milwaukee to Southwest Florida International Airport (rsw), simply search for flights on our website and select the desired airline, such as Southwest Airlines (WN), and choose your preferred travel dates.
Can I get a fare comparison for flights from Milwaukee to Southwest Florida International Airport (rsw) via other airlines?
Yes, you can get a fare comparison for flights from Milwaukee to Southwest Florida International Airport (rsw) via other airlines, such as Porter Airline (PD), American Airlines (AA), Allegiant (G4), JetBlue Airways (B6), United Airlines (UA), WestJet Airlines (WS), Air Transat (TS), Volaris Airline (Y4), and Delta Airlines (DL).
How do I find the best airline for my Southwest Florida International Airport (rsw) destination?
To find the best airline for your Southwest Florida International Airport (rsw) destination, compare fares on our website and choose the airline that best suits your needs, such as Southwest Airlines (WN), which is known for its affordable fares and convenient flight schedules.
How can I search for flights from Milwaukee to Southwest Florida International Airport (rsw) on your website?
To search for flights from Milwaukee to Southwest Florida International Airport (rsw) on our website, simply enter your travel dates and destinations in the search bar and select the desired airline, such as Southwest Airlines (WN), and choose your preferred travel dates.

Chicago (MDW) to Fort Myers (RSW): Airport Information

Origin Airport Chicago Midway International , Chicago, US
Destination Airport Southwest Florida International , Fort Myers, US
Distance 1105 miles

More Flight Options for Chicago (MDW) and Fort Myers (RSW)

Why Fareleaders for MDW to RSW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Chicago to Fort Myers flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on MDW to RSW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Chicago to Fort Myers flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Chicago (MDW) to Fort Myers (RSW)
Terms and Conditions*