Cheap flights from Chicago to Sarasota from $64

The cheapest month to fly to Sarasota from Chicago is in January. Flight prices, which tend to average around $298, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Sarasota from Chicago during August instead. Flights to Sarasota in August, while not as cheap as those in January, still average around $302.

The cheapest day to depart from Chicago to Sarasota is on a Sunday when prices can be found for as low as $295. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Sarasota for around $434.

The cheapest time of day to fly to Sarasota is in the afternoon when flights can be purchased for as low as $335. In the evening is when there is more demand to fly to Sarasota, so prices are often more expensive at around $439 per ticket.

Fly from Chicago Greater Rockford to Sarasota Bradenton Intl for the best Chicago - Sarasota Bradenton Intl flight prices

You are more likely to see cheaper flights to Sarasota from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Sarasota for around $406 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Sarasota from Chicago for as low as $359 on momondo.

There are 4 cabin classes available to choose from on Chicago to Sarasota 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 to Sarasota.

As of September 2026, prices for Chicago to Sarasota flights are approximately 26% cheaper when compared to flights at the same time last year.

Allegiant Air, United Airlines, and Southwest are the most popular carriers operating from Chicago to Sarasota Bradenton Intl

United Airlines, Allegiant Air and American Airlines are the top three most popular airlines that fly to Sarasota from Chicago according to our data. United Airlines is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Sarasota. Keep in mind that there are 7 different airlines that fly to Sarasota on a routine basis, so you have a few additional options to choose from.

Nashville (BNA) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Atlanta (ATL) offer the lowest average round-trip price of $298.

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 4h 16m.

Nashville (BNA) has the shortest average layover time for this route: 0h 53m.

The number of flights available between Chicago and Sarasota is 7 per day as of September 2026. The most frequent departure time is 11:00AM, with 94% of daily flights leaving at noon.

50 flights are operational weekly from Chicago to Sarasota as of September 2026. The most popular departure day for this route is Sun, with 18% of flights per week taking off on this day.