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Flights from Chicago to Florida

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Flight deals from Chicago to Florida

Looking for cheap tickets from Chicago to Florida, or a last-minute trip? Find the lowest prices on one-way and return tickets right here.
Orlando.R 1,398 per passenger.Departing Mon, 12 May, returning Wed, 21 May.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 12 May, arriving in Orlando Sanford.Inbound direct flight with Allegiant Air departs from Orlando Sanford on Wed, 21 May, arriving in Chicago Rockford.Price includes taxes and charges.From R 1,398, select.
Tampa.R 1,445 per passenger.Departing Wed, 14 May, returning Wed, 21 May.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Wed, 14 May, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Wed, 21 May, arriving in Chicago Rockford.Price includes taxes and charges.From R 1,445, select.
Sarasota.R 1,656 per passenger.Departing Sun, 11 May, returning Wed, 21 May.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Sun, 11 May, arriving in Sarasota.Inbound direct flight with Allegiant Air departs from Sarasota on Wed, 21 May, arriving in Chicago Rockford.Price includes taxes and charges.From R 1,656, select.
Punta Gorda.R 1,681 per passenger.Departing Sun, 11 May, returning Thu, 22 May.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Sun, 11 May, arriving in Punta Gorda.Inbound direct flight with Allegiant Air departs from Punta Gorda on Thu, 22 May, arriving in Chicago Midway.Price includes taxes and charges.From R 1,681, select.
Miami.R 1,801 per passenger.Departing Tue, 16 Sep, returning Sat, 20 Sep.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Tue, 16 Sep, arriving in Miami International.Inbound direct flight with Spirit Airlines departs from Miami International on Sat, 20 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,801, select.
Fort Lauderdale.R 1,806 per passenger.Departing Tue, 20 May, returning Tue, 3 Jun.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Tue, 20 May, arriving in Fort Lauderdale International.Inbound direct flight with Spirit Airlines departs from Fort Lauderdale International on Tue, 3 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,806, select.
Fort Myers.R 2,413 per passenger.Departing Sat, 18 Oct, returning Tue, 21 Oct.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Sat, 18 Oct, arriving in Fort Myers Southwest Florida Reg.Inbound direct flight with Spirit Airlines departs from Fort Myers Southwest Florida Reg on Tue, 21 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,413, select.
Pensacola.R 3,003 per passenger.Departing Sun, 18 May, returning Thu, 22 May.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sun, 18 May, arriving in Pensacola.Inbound indirect flight with Spirit Airlines, departs from Pensacola on Thu, 22 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 3,003, select.

Flying from Chicago to Florida

Arm yourself with these facts on the fly.
Cheapest flight foundR 681, Orlando
Cheapest month to flyMay
Average flight time2 hrs, 41 mins
Cheapest airport to fly fromChicago Rockford
Most popular airlineAmerican Airlines

Frequently asked questions

We looked at all of the upcoming return flights from Chicago to Florida we could find over the next 12 months. It looks like R 1,398 is the best price. This is good, compared to the average Florida ticket price of R 5,475.
The cheapest month to fly from Chicago to Sarasota Airport is usually May. The cheapest month to fly from Chicago to Jacksonville International Airport is usually June. The cheapest month to fly from Chicago to Miami International Airport is usually September. And the cheapest month to fly from Chicago to Gainesville Airport is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Florida on Monday, 12 May 2025.
If you're flying from Chicago, the cheapest city in Florida to fly into is Orlando. The cheapest airport serving Orlando at the moment is Orlando Sanford.
The average flight time between Chicago and Florida is 2 hours and 40 minutes.

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