Cheap flights from Tampa to Chicago from $106

The month of October is, on average, the cheapest month to fly to Chicago from Tampa, with most prices found around $198. If you’re not able to fly to Chicago in October, then February is your next best option. Flight prices from Tampa to Chicago during February average around $203.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $340. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Tampa to Chicago for around $523.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Tampa to Chicago during this time can be as low as $318. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $400.

Fly from Tampa to Chicago Midway for the best Tampa - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Tampa when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $282 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Tampa for as low as $233 on momondo.

There are 4 cabin classes available to choose from on Tampa to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 25% on your flight if you consider stops on a Tampa to Chicago flight.

As of August 2026, prices for Tampa to Chicago flights are approximately 76% more expensive when compared to flights at the same time last year.

Southwest, Delta, and United Airlines are the most popular carriers operating from Tampa to Chicago

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago from Tampa according to our data. United Airlines is the first choice among our users, with 31% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of August 2026, there are 33 flights per day flying from Tampa to Chicago. The most common time of day flights depart is 12:00PM, with 59% of flights taking off in the afternoon.

As of August 2026, there are 235 flights per week flying from Tampa to Chicago. The most common day of the week flights depart is Wed, with 17% of flights taking off on this day.