Cheap flights from Sarasota to Chicago from $57

The month of September is, on average, the cheapest month to fly to Chicago from Sarasota, with most prices found around $353. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from Sarasota to Chicago during May average around $364.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $382. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Sarasota to Chicago for around $514.

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Sarasota to Chicago during this time can be as low as $343. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $451.

Fly from Sarasota Bradenton Intl to Chicago O'Hare Intl for the best Sarasota Bradenton Intl - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Sarasota when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $393 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Sarasota for as low as $308 on momondo.

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

As of September 2026, prices for Sarasota to Chicago flights are approximately 74% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Sarasota according to our data. United Airlines is the first choice among our users, with 43% 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.

The number of flights available between Sarasota and Chicago is 2 per day as of September 2026. The most frequent departure time is 4:00PM, with 91% of daily flights leaving in the afternoon.

As of September 2026, there are 14 flights per week flying from Sarasota to Chicago. The most common day of the week flights depart is Thu, with 29% of flights taking off on this day.