The cheapest ticket to Florida from Chicago found in the last 72 hours was $26 one-way, and $38 round-trip. The most popular route is from Chicago to West Palm Beach , and the cheapest round-trip airline ticket found on this route in the last 72 hours was $40.

Find United Airlines cheap flights from Chicago to Orlando. Enjoy a Chicago to Orlando modern flight experience in premium cabins with Wi-Fi.

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Orlando in 2025. You can also book with separate airlines for your outbound and return journeys, from $24 one-way.

Find flights to Florida from $24. Fly from Chicago O'Hare Airport on Frontier, Spirit Airlines and more. Search for Florida flights on KAYAK now to find the best deal.

Cheap Flights from Chicago (ORD) to Tampa (TPA) start at $24 for one-way and $48 for round trip. Earn your airline miles on top of our rewards!

Fly one-way from Chicago (Midway) to Fort Lauderdale starting at $119. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

Looking for cheap flights from Chicago to Florida, or a last-minute trip? Find the lowest prices on one-way and round-trip flights right here.

6 days ago · Find United Airlines cheap flights from Chicago to Fort Lauderdale. Enjoy a Chicago to Fort Lauderdale modern flight experience in premium cabins with Wi-Fi.

Flying to Florida from Chicago in the evening is the least expensive time of day to depart. momondo users have found prices as low as $201 when looking at flights departing in the evening. Flights to Florida are more costly in the morning, with an average ticket price of $491.

Our data shows that the cheapest route for a return flight from Chicago to Orlando Sanford Intl Airport cost $155 and was between Chicago Greater Rockford Airport (RFD) and Orlando Sanford Intl Airport (SFB). On average, the best prices are found if you fly this route.