Cheap flights from Chicago Midway Airport to Tampa from $99

The month of October is, on average, the cheapest month to fly to Tampa from Chicago Midway Airport, with most prices found around $157. If you aren’t able to travel to Tampa during the month of October, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $157.

The cheapest day to depart from Chicago Midway Airport to Tampa is on a Wednesday. Travelers who choose to depart for Tampa on a Wednesday will often find tickets for as low as $277. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Tampa on Monday is $341.

The cheapest time of day to fly to Tampa is in the evening when flights can be purchased for as low as $282. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $303 on average. Flights to Tampa from Chicago Midway Airport at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

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

You are more likely to see cheaper flights to Tampa from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Tampa for around $281 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Tampa from Chicago Midway Airport for as low as $221 on momondo.

There is only 1 cabin class available to choose from on Chicago Midway Airport to Tampa flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Tampa.

As of June 2026, prices for Chicago Midway Airport to Tampa flights are approximately 133% more expensive when compared to flights at the same time last year.

Historically, on average around 19% of flights between Chicago and Tampa have experienced a delay on any given week. The average delay length over the past 12 months has been 126 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 19% of their flights experiencing any sort of delay.

Detroit (DTW) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

Flights via Atlanta (ATL) offer the lowest average round-trip price of $368.

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 4h 02m.

Atlanta (ATL) has the shortest average layover time for this route: 1h 14m.

The number of flights available between Chicago Midway Airport and Tampa is 3 per day as of June 2026. The most frequent departure time is 5:00AM, with 42% of daily flights leaving in the afternoon.

27 flights are operational weekly from Chicago Midway Airport to Tampa as of June 2026. The most popular departure day for this route is Sat, with 22% of flights per week taking off on this day.