Cheap flights from Tampa to Chicago from $109

The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from Tampa, with most prices found around $204. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Tampa during the month November is also very affordable. Most momondo users find prices during this month for around $245.

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Tampa. The lowest ticket price found for a Friday departure recently was $292. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Tampa because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $385.

Flying to Chicago Midway Airport from Tampa at noon is the least expensive time of day to depart. momondo users have found prices as low as $246 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $359. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago Midway Airport from Tampa when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $312 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Tampa for as low as $232 on momondo.

There is only 1 cabin class available to choose from on Tampa to Chicago Midway Airport 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 19% on your flight if you consider stops on a Tampa to Chicago Midway Airport flight.

As of August 2026, prices for Tampa to Chicago Midway Airport flights are approximately 209% more expensive when compared to flights at the same time last year.

Southwest is the most popular carrier operating from Tampa to Chicago Midway

Southwest, Frontier and JetBlue are the top three most popular airlines that fly to Chicago Midway Airport from Tampa according to our data. Southwest is the first choice among our users, with 63% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

2 flights are operational daily from Tampa to Chicago Midway Airport as of August 2026. The most popular departure time for this route is 11:00AM, with 53% of flights per day taking off at noon.

As of August 2026, there are 15 flights per week flying from Tampa to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 33% of flights taking off on this day.