Cheap flights from Sarasota to Chicago from $143

The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Sarasota averaging around $372.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as $387. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Sarasota because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $551.

Flying to Chicago O'Hare Intl Airport from Sarasota at noon is the least expensive time of day to depart. momondo users have found prices as low as $372 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $478. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Sarasota when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $409 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Sarasota for as low as $303 on momondo.

There are 4 cabin classes available to choose from on Sarasota to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport.

As of October 2026, prices for Sarasota to Chicago O'Hare Intl Airport flights are approximately 24% cheaper when compared to flights at the same time last year.

Sun Country Air, United Airlines, and Delta are the most popular carriers operating from Sarasota Bradenton Intl to Chicago O'Hare Intl

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Sarasota according to our data. United Airlines is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 6 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

6 flights are operational daily from Sarasota to Chicago O'Hare Intl Airport as of October 2026. The most popular departure time for this route is 4:00PM, with 100% of flights per day taking off in the afternoon.

As of October 2026, there are 46 flights per week flying from Sarasota to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.