Cheap Flights from Chicago to Fort Myers (MDW to RSW)

Swap the chilly winds of Chicago for the sunny shores of Fort Myers with affordable flights from Globitude Travels. Flying out of Chicago Midway (MDW) to Southwest Florida International Airport (RSW) is one of the easiest ways to escape to warm beaches, vibrant seafood spots, and relaxed coastal vibes. Book your getaway today and save on top airlines!

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Fly from Chicago Midway to Sunny Fort Myers

Traveling from Chicago Midway Airport (MDW) to Southwest Florida International Airport (RSW) in Fort Myers connects you straight to Florida's Gulf Coast. Fort Myers is famous for its year-round sunshine, shell-lined beaches like Sanibel Island, and historic attractions such as the Edison and Ford Winter Estates. Whether you are seeking a quick weekend escape from Midwest winters or a longer tropical vacation, this route offers convenient travel options.

When planning your trip, consider Southwest Florida's tropical climate. Winter and spring bring warm, dry days ideal for sightseeing, while summer offers balmy beach weather and fewer crowds. Upon landing at RSW, you will find easy access to downtown Fort Myers, nearby Naples, and stunning barrier islands where fresh Gulf seafood and waterfront dining await.

Money-saving tips for this route

Fly during mid-week days like Tuesday or Wednesday to secure lower fares on flights from MDW to RSW.
Book your travel at least three to four weeks in advance to get the best Economy rates on Delta and Southwest.
Review baggage policies before booking, as Southwest includes two free checked bags while Delta Economy fares may charge extra.
Consider traveling during shoulder seasons like May or September to enjoy great Florida weather with fewer tourists and discounted airfare.

Frequently asked questions

Which airlines fly from Chicago (MDW) to Fort Myers (RSW)?

Globitude Travels offers competitive Economy rates on Southwest Airlines starting from $250 and Delta Air Lines starting from $251 for MDW to RSW flights.

What are the primary airports for this flight route?

Your flight departs from Chicago Midway International Airport (MDW) in Illinois and arrives at Southwest Florida International Airport (RSW) in Fort Myers.

What is generally the cheapest month to fly to Fort Myers?

Late summer and early fall, particularly September and October, generally offer the lowest airfares and hotel rates for travel to Fort Myers.

Are flights between Chicago Midway and Fort Myers direct or connecting?

Both nonstop flights and options with convenient single stops are available on this route depending on the airline and departure date.

Can I book my MDW to RSW flight over the phone?

Yes, you can call Globitude Travels customer support directly to reserve your tickets, check live fare availability, or get assistance with your travel plans.

Related routes

↩ Fort Myers to Chicago Chicago to Atlanta Chicago to Cancún Chicago to Charlotte Chicago to Denver Chicago to Fort Lauderdale Chicago to Houston Albuquerque to Fort Myers Charleston to Fort Myers Chicago to Fort Myers Des Moines to Fort Myers Detroit to Fort Myers Evansville to Fort Myers All routes →

Why book with Globitude Travels

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Globitude Travels is an independent travel agency — call 1-856-513-6369 or use the search above to compare live fares on this route. See our terms, privacy policy, refund policy and service fees for full details, or contact us any time.

Page updated September 13, 2026 · fare data refreshed automatically from live flight searches.