$54 Cheap flights from Midway Intl. to Southwest Florida Intl. (MDW to RSW)

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Find The Best Dates To Fly from Midway Intl. to Southwest Florida Intl.

Amazing MDW to RSW Flight Deals

The cheapest flights to Southwest Florida Intl. found within the past 7 days were $134 round trip and $54 one way. Prices and availability subject to change. Additional terms may apply.

Sat, May 4 - Wed, May 22
MDW
Chicago
RSW
Fort Myers
$134 Roundtrip, found 2 days ago
$134
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 4 from Chicago to Fort Myers, returning Wed, May 22, priced at $134 found 2 days ago
Wed, May 22 - Wed, May 29
MDW
Chicago
RSW
Fort Myers
$139 Roundtrip, found 8 hours ago
$139
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, May 22 from Chicago to Fort Myers, returning Wed, May 29, priced at $139 found 8 hours ago
Mon, May 20 - Fri, May 31
MDW
Chicago
RSW
Fort Myers
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, May 20 from Chicago to Fort Myers, returning Fri, May 31, priced at $147 found 2 days ago
Thu, May 16 - Mon, May 20
MDW
Chicago
RSW
Fort Myers
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 16 from Chicago to Fort Myers, returning Mon, May 20, priced at $160 found 2 days ago
Sat, Apr 27 - Thu, May 9
MDW
Chicago
RSW
Fort Myers
$162 Roundtrip, found 3 days ago
$162
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Apr 27 from Chicago to Fort Myers, returning Thu, May 9, priced at $162 found 3 days ago
Sat, May 11 - Wed, May 29
MDW
Chicago
RSW
Fort Myers
$163 Roundtrip, found 2 days ago
$163
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 11 from Chicago to Fort Myers, returning Wed, May 29, priced at $163 found 2 days ago
Sat, May 11 - Sun, May 12
MDW
Chicago
RSW
Fort Myers
$164 Roundtrip, found 7 hours ago
$164
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, May 11 from Chicago to Fort Myers, returning Sun, May 12, priced at $164 found 7 hours ago
Mon, May 20 - Wed, May 29
MDW
Chicago
RSW
Fort Myers
$165 Roundtrip, found 2 days ago
$165
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, May 20 from Chicago to Fort Myers, returning Wed, May 29, priced at $165 found 2 days ago
Tue, Jun 4 - Sat, Jun 8
MDW
Chicago
RSW
Fort Myers
$170 Roundtrip, found 2 days ago
$170
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jun 4 from Chicago to Fort Myers, returning Sat, Jun 8, priced at $170 found 2 days ago
Sat, May 11 - Fri, May 31
MDW
Chicago
RSW
Fort Myers
$171 Roundtrip, found 5 days ago
$171
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 11 from Chicago to Fort Myers, returning Fri, May 31, priced at $171 found 5 days ago

Best Southwest Florida Intl. Flight and Hotel Packages

Southwest Florida Intl. flight + hotel packages - economy flights

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
per person
May 19 - May 23
Roundtrip flight included
Chicago (CHI) to Fort Myers (RSW)
South Seas Resort

South Seas Resort

3.5 out of 5
Save 100% on your flight
per person
May 19 - May 23
Roundtrip flight included
Chicago (CHI) to Fort Myers (RSW)
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Save 100% on your flight
per person
May 19 - May 23
Roundtrip flight included
Chicago (CHI) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
per person
May 19 - May 23
Roundtrip flight included
Chicago (CHI) to Fort Myers (RSW)
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Save 100% on your flight
per person
May 19 - May 23
Roundtrip flight included
Chicago (CHI) to Fort Myers (RSW)
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Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I catch a flight from MDW to RSW right now?
For information on any current Southwest Florida Intl. Airport (RSW) travel advice and quarantine requirements, visit our Covid-19 Travel Advisor. Look before you arrange your flight, so you don’t get caught up en route.
Are there direct flights from Midway Airport to RSW?
If you can’t wait to get started on your sightseeing adventures in Fort Myers, fly with Southwest Airlines. This airline operates nonstop flights from Midway Airport to Southwest Florida Intl. Airport.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to RSW, please visit our Customer Service Portal.
How long is the flight from MDW to Southwest Florida Intl. Airport?
The flight from Chicago to Fort Myers is a mere 2 hours and 45 minutes in total. With such a short travel time, you won’t need to fret if you forget to pack a phone charger in your carry-on luggage.
What is the flight distance from Chicago Airport to Southwest Florida Intl. Airport?
You’ll need to journey about 1,100 mi from MDW to Southwest Florida Intl. Airport before you can officially kick-start your vacation. Order a refreshment when the drink cart comes by and watch one or two of your favorite movies. You’ll have lots of time!
What airlines fly from Chicago Airport to RSW?
Eager to fly direct from Chicago to Fort Myers? Southwest Airlines (WN) offers 117 flights per month and is a popular choice with many wise wanderers.
What airlines have practices regarding COVID-19 in place and use social distancing?
From the moment you enter the departure terminal to when you leave the arrivals terminal, if you’re flying with Southwest Airlines, United Airlines or Delta you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It’s possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

 

Traveling From
Midway Intl.
Traveling To
Southwest Florida Intl.
Shortest Flight Time
2 hours 40 mins
Earliest Departure Time
7:45AM CDT
Latest Departure Time
8:10PM CDT
Lowest Flight Price
$134

Route Info

Flight path for flights from Chicago Midway International Airport to Southwest Florida International Airport.


Origin:
MDW - Chicago Midway International Airport
Destination:
RSW - Southwest Florida International Airport
Distance:
1,113.00 miles


Discover our best flights from Chicago MDW to Fort Myers RSW. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Chicago MDW to Fort Myers RSW at the right price  

Airfares to Fort Myers RSW from Chicago MDW currently cost between $134 and $171. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Chicago MDW to Fort Myers RSW 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Chicago MDW to Fort Myers RSW on Travelocity starting at $54. Prices and availability subject to change. Additional terms may apply. 

 

Get to Fort Myers RSW from Chicago MDW quicker with direct flights. 

Get to Fort Myers faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to RSW from MDW to take around 2 hour(s) 40 min(s).  

 

Find our cheapest airfares for flights from Chicago MDW to Fort Myers RSW

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to RSW from MDW. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Chicago MDW to Fort Myers RSW today 

If you’re flexible about when you travel, May is usually the cheapest month to fly from Chicago MDW to Fort Myers RSW. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Fort Myers RSW from Chicago MDW 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to RSW from MDW have this option.  

 

Travel with confidence when you book flights to Fort Myers RSW from Chicago MDW with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.