Flights from Chicago to Florida

Flight deals from Chicago to Florida

Looking for a cheap last-minute deal or the best return flight from Chicago to Florida? If you want to travel next month, return fares start from 65 €. Find the lowest prices on one-way and return tickets right here.

Fort Lauderdale.65 € per passenger.Departing Thu, 16 Jul, returning Thu, 6 Aug.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Thu, 16 Jul, arriving in Fort Lauderdale International.Inbound direct flight with Allegiant Air departs from Fort Lauderdale International on Thu, 6 Aug, arriving in Chicago Rockford.Price includes taxes and charges.From 65 €, select.

Orlando.72 € per passenger.Departing Wed, 21 Oct, returning Fri, 30 Oct.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Wed, 21 Oct, arriving in Orlando Sanford.Inbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 30 Oct, arriving in Chicago Rockford.Price includes taxes and charges.From 72 €, select.

Tampa.80 € per passenger.Departing Mon, 31 Aug, returning Fri, 18 Sep.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 31 Aug, arriving in St. Pete–Clearwater International.Inbound direct flight with Allegiant Air departs from St. Pete–Clearwater International on Fri, 18 Sep, arriving in Chicago Rockford.Price includes taxes and charges.From 80 €, select.

Sarasota.86 € per passenger.Departing Wed, 12 Aug, returning Sat, 15 Aug.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Wed, 12 Aug, arriving in Sarasota.Inbound direct flight with Allegiant Air departs from Sarasota on Sat, 15 Aug, arriving in Chicago Rockford.Price includes taxes and charges.From 86 €, select.

Destin.90 € per passenger.Departing Mon, 29 Jun, returning Mon, 20 Jul.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Midway on Mon, 29 Jun, arriving in Destin-Ft Walton Beach.Inbound direct flight with Allegiant Air departs from Destin-Ft Walton Beach on Mon, 20 Jul, arriving in Chicago Midway.Price includes taxes and charges.From 90 €, select.

Jacksonville.157 € per passenger.Departing Thu, 13 Aug, returning Sun, 16 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 13 Aug, arriving in Jacksonville International.Inbound indirect flight with Frontier Airlines, departs from Jacksonville International on Sun, 16 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 157 €, select.

Miami.172 € per passenger.Departing Wed, 12 Aug, returning Wed, 19 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 12 Aug, arriving in Miami International.Inbound direct flight with Southwest Airlines departs from Miami International on Wed, 19 Aug, arriving in Chicago Midway.Price includes taxes and charges.From 172 €, select.

Pensacola.192 € per passenger.Departing Fri, 28 Aug, returning Tue, 1 Sep.Return flight with Frontier Airlines and Breeze Airways.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri, 28 Aug, arriving in Pensacola.Inbound indirect flight with Breeze Airways, departs from Pensacola on Tue, 1 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 192 €, select.

Fort Myers.196 € per passenger.Departing Thu, 10 Sep, returning Mon, 14 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 10 Sep, arriving in Fort Myers Southwest Florida Reg.Inbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Mon, 14 Sep, arriving in Chicago Midway.Price includes taxes and charges.From 196 €, select.

Panama City.208 € per passenger.Departing Wed, 2 Sep, returning Wed, 9 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 2 Sep, arriving in Northwest Florida Beaches International.Inbound indirect flight with Southwest Airlines, departs from Northwest Florida Beaches International on Wed, 9 Sep, arriving in Chicago Midway.Price includes taxes and charges.From 208 €, select.

Key West.209 € per passenger.Departing Thu, 13 Aug, returning Thu, 20 Aug.Return flight with Allegiant Air and Breeze Airways.Outbound indirect flight with Allegiant Air, departs from Chicago Midway on Thu, 13 Aug, arriving in Key West International.Inbound indirect flight with Breeze Airways, departs from Key West International on Thu, 20 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 209 €, select.

West Palm Beach.216 € per passenger.Departing Thu, 16 Jul, returning Sun, 19 Jul.Return flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Thu, 16 Jul, arriving in West Palm Beach International.Inbound indirect flight with Allegiant Air, departs from West Palm Beach International on Sun, 19 Jul, arriving in Chicago Midway.Price includes taxes and charges.From 216 €, select.

Tallahassee.227 € per passenger.Departing Sat, 1 Aug, returning Tue, 4 Aug.Return flight with Frontier Airlines and Breeze Airways.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 1 Aug, arriving in Tallahassee.Inbound indirect flight with Breeze Airways, departs from Tallahassee on Tue, 4 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 227 €, select.

Melbourne.260 € per passenger.Departing Sat, 31 Oct, returning Sat, 7 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 31 Oct, arriving in Melbourne Orlando International.Inbound indirect flight with Delta, departs from Melbourne Orlando International on Sat, 7 Nov, arriving in Chicago Midway.Price includes taxes and charges.From 260 €, select.

Daytona Beach.265 € per passenger.Departing Tue, 11 Aug, returning Tue, 18 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 11 Aug, arriving in Daytona Beach.Inbound indirect flight with Delta, departs from Daytona Beach on Tue, 18 Aug, arriving in Chicago Midway.Price includes taxes and charges.From 265 €, select.

Gainesville.343 € per passenger.Departing Wed, 1 Jul, returning Tue, 7 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Wed, 1 Jul, arriving in Gainesville.Inbound indirect flight with Delta, departs from Gainesville on Tue, 7 Jul, arriving in Chicago Midway.Price includes taxes and charges.From 343 €, select.

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Flying from Chicago to Florida

Arm yourself with these facts on the fly.

Cheapest flight found	65 €
Cheapest month to fly	July
Average flight time	2 hrs, 45 mins
Cheapest airport to fly from	Chicago Rockford
Most popular airline	American Airlines

How to find cheap flights from Chicago to Florida

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago to Florida. Other savvy travellers recently found return flights from 65 € and one-way tickets from 33 € one-way. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago Rockford into Fort Lauderdale International

At the moment, the lowest priced flight tickets to Florida are from Chicago Rockford Airport to Fort Lauderdale International Airport.

Fly in July

We crunched the flight calendar and found the cheapest time to fly from Chicago to Florida is currently July.

Flex your dates for the best rates

If you’re flexible on your departure dates, you can use Skyscanner's whole month tool to find the cheapest day of the year to fly from Chicago to anywhere you choose in Florida.

Watch as fares rise and fall

With Price Alerts, we'll let you know when flight prices from Chicago to Florida go up or down so you can book when the time is just right.

Relax – these are fee-free flight tickets

With us, there are no added fees – the Florida to Florida flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

What's the average Chicago to Florida flight price?

We looked at all of the upcoming return flights from Chicago to Florida we could find over the next 12 months. It looks like 65 € is the best price. This is good, compared to the average Florida ticket price of 200 €.

What is the cheapest month to fly from Chicago to Florida?

The cheapest month to fly from Chicago to Lakeland Airport is usually June. The cheapest month to fly from Chicago to St. Pete–Clearwater International Airport is usually August. The cheapest month to fly from Chicago to Sarasota Airport is usually August. And the cheapest month to fly from Chicago to Miami International Airport is usually August.

Which upcoming date is cheapest to fly from Chicago to Florida on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Florida on Thursday, 16 July 2026.

Are there any direct flights from Chicago to Florida?

Chicago Rockford Airport, Chicago Midway Airport and Chicago O'Hare International Airport all offer direct flights to Florida.

If I'm flying from Chicago, where in Florida is cheapest to fly into?

If you're flying from Chicago, the cheapest city in Florida to fly into is Fort Lauderdale. The cheapest airport serving Fort Lauderdale at the moment is Fort Lauderdale International.