Cheap flights to Florida from Chicago

Round trips from Chicago from $117. Cheapest dates, deal ratings and where to book.

• Miami: $117, 2026-11-07 to 2026-11-17
• Tampa: $120, 2026-10-28 to 2026-11-04
• Jacksonville: $155, 2026-11-04 to 2026-11-06
• Orlando: $176, 2026-11-07 to 2026-11-16
• Panama City Beach: $249, 2027-02-22 to 2027-02-26
• Fort Myers: $280, 2026-10-28 to 2026-11-05
• Sarasota/Bradenton: $295, 2026-10-15 to 2026-10-18
• Daytona Beach: $323, 2026-10-16 to 2026-10-23

Nearby

• Georgia
• South Carolina
• Alabama
• North Carolina
• Mississippi
• Tennessee
• Louisiana
• Kentucky