Plane tickets from Chicago to Clearwater

As of May 2020, the minimum price for a direct flight from Clearwater, Florida to Chicago, Illinois is around $187. Prices may vary depending on time of booking and airline. The number of times a week that planes fly from Clearwater to Chicago varies depending on the airline and the time of year. For example, American Airlines operates daily direct flights from Clearwater International Airport (PIE) to Chicago O'Hare International Airport (ORD) during the summer months (May–October). During the rest of the year, American typically operates the route three times a week on Mondays, Thursdays, and Saturdays. Other airlines may offer additional flights on this route. The best time to fly from Clearwater to Chicago is typically in the early morning or late evening in order to avoid the peak travel times. Additionally, the most cost-effective flight will usually be the one with the least number of stops. The frequency of flight departure times between Clearwater, Florida and Chicago, Illinois depends on the airline and the time of year. Generally speaking, there are several flights per day during peak season. No, if you are a US citizen, you do not need a visa to travel from Clearwater, FL to Chicago, IL. However, you must have a valid passport. 1. American Airlines 2. Delta Air Lines 3. United Airlines 4. Southwest Airlines 5. Frontier Airlines American Airlines, United Airlines, and Delta Airlines all fly from Clearwater, Florida to Chicago, Illinois.