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Flights from Chicago Midway Airport to Florida

Flight deals from Chicago Midway Airport to Florida

Looking for cheap tickets from Chicago Midway Airport to Florida, or a last-minute trip? Find the lowest prices on one-way and return tickets right here.
Miami.$51 per passenger.Departing Sat, 11 Apr.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Sat, 11 Apr, arriving in Miami International.Price includes taxes and charges.From $51, select.
Orlando.$61 per passenger.Departing Mon, 2 Mar.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Mon, 2 Mar, arriving in Orlando International.Price includes taxes and charges.From $61, select.
Destin.$63 per passenger.Departing Sun, 8 Mar.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Sun, 8 Mar, arriving in Destin-Ft Walton Beach.Price includes taxes and charges.From $63, select.
Punta Gorda.$70 per passenger.Departing Sun, 19 Apr.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Sun, 19 Apr, arriving in Punta Gorda.Price includes taxes and charges.From $70, select.
Fort Lauderdale.$82 per passenger.Departing Mon, 23 Feb.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 23 Feb, arriving in Fort Lauderdale International.Price includes taxes and charges.From $82, select.
Tampa.$89 per passenger.Departing Wed, 11 Mar.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 11 Mar, arriving in Tampa International.Price includes taxes and charges.From $89, select.
Fort Myers.$90 per passenger.Departing Fri, 27 Feb.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 27 Feb, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From $90, select.
Jacksonville.$91 per passenger.Departing Mon, 2 Mar.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 2 Mar, arriving in Jacksonville International.Price includes taxes and charges.From $91, select.
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Flying from Chicago Midway Airport to Florida

Arm yourself with these facts on the fly.
Cheapest flight found$51
Cheapest month to flyApril
Average flight time2 hrs, 35 mins
Average flights per week332
Most popular airlineSouthwest Airlines

Frequently asked questions

Chicago O'Hare International Airport and Chicago Rockford Airport all offer direct flights to Florida.
We looked at all of the upcoming return flights from Chicago Midway Airport to Florida we could find over the next 12 months. It looks like $88 is the best price. This is good, compared to the average Florida ticket price of $265.
The cheapest month to fly from Chicago Midway Airport to Gainesville Airport is currently March.
The cheapest month to fly from Chicago Midway Airport to Key West International Airport is currently August.
The cheapest month to fly from Chicago Midway Airport to Miami International Airport is currently March.
And the cheapest month to fly from Chicago Midway Airport to West Palm Beach International Airport is usually February.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago Midway Airport to Florida on Sunday, 1 March 2026.
If you're flying from Chicago Midway, the cheapest city in Florida to fly into is Miami. The cheapest airport serving Miami at the moment is Miami International.
The average flight time between Chicago Midway Airport and Florida is 2 hours and 35 minutes.