Skyscanner

Flights from Chicago to Florida

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.$125 per passenger.Departing Fri, 4 Jul, returning Sat, 12 Jul.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Fri, 4 Jul, arriving in Orlando Sanford.Inbound direct flight with Allegiant Air departs from Orlando Sanford on Sat, 12 Jul, arriving in Chicago Rockford.Price includes taxes and charges.From $125, select.
Tampa.$126 per passenger.Departing Wed, 27 Aug, returning Fri, 5 Sep.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Wed, 27 Aug, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Fri, 5 Sep, arriving in Chicago Rockford.Price includes taxes and charges.From $126, select.
Fort Myers.$133 per passenger.Departing Sun, 13 Jul, returning Sun, 13 Jul.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Sun, 13 Jul, arriving in Fort Myers Southwest Florida Reg.Inbound direct flight with Spirit Airlines departs from Fort Myers Southwest Florida Reg on Sun, 13 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $133, select.
Punta Gorda.$135 per passenger.Departing Sat, 9 Aug, returning Sun, 17 Aug.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Sat, 9 Aug, arriving in Punta Gorda.Inbound direct flight with Allegiant Air departs from Punta Gorda on Sun, 17 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $135, select.
Sarasota.$150 per passenger.Departing Sun, 12 Oct, returning Thu, 30 Oct.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Sun, 12 Oct, arriving in Sarasota.Inbound direct flight with Allegiant Air departs from Sarasota on Thu, 30 Oct, arriving in Chicago Rockford.Price includes taxes and charges.From $150, select.
Miami.$178 per passenger.Departing Wed, 16 Jul, returning Tue, 29 Jul.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Wed, 16 Jul, arriving in Miami International.Inbound direct flight with Spirit Airlines departs from Miami International on Tue, 29 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $178, select.
Fort Lauderdale.$178 per passenger.Departing Mon, 14 Jul, returning Tue, 15 Jul.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Mon, 14 Jul, arriving in Fort Lauderdale International.Inbound direct flight with Spirit Airlines departs from Fort Lauderdale International on Tue, 15 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $178, select.
Pensacola.$287 per passenger.Departing Tue, 15 Jul, returning Sat, 2 Aug.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 15 Jul, arriving in Pensacola.Inbound indirect flight with Spirit Airlines, departs from Pensacola on Sat, 2 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $287, select.

Flying from Chicago to Florida

Arm yourself with these facts on the fly.
Cheapest flight found$125, Orlando
Cheapest month to flyJuly
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 $125 is the best price. This is good, compared to the average Florida ticket price of $496.
The cheapest month to fly from Chicago to St. Pete–Clearwater International Airport is usually August. The cheapest month to fly from Chicago to Jacksonville International Airport is usually August. The cheapest month to fly from Chicago to Sarasota Airport is usually October. And the cheapest month to fly from Chicago to Miami International Airport is usually July.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Florida on Friday, 4 July 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 41 minutes.

More travel options

OSZAR »