Cheap flights from Chicago to Valparaiso from $59

If you aren’t able to travel during the month of October, then book flights to Valparaiso, Florida from Chicago during January instead. Flights to Valparaiso, Florida in January, while not as cheap as those in October, still average around $372.

The cheapest day to depart on your flight to Valparaiso, Florida is on a Monday when prices can be found for as low as $168. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $413.

Our data shows that the cheapest Chicago to Valparaiso, Florida flights are usually those with departure times in the afternoon. Our users have found flights to Valparaiso, Florida in the afternoon for as low as $186. In contrast, the most expensive time of day to depart to Valparaiso, Florida is in the morning when prices are around $435.

Fly from Chicago Midway to Valparaiso Destin-Ft Walton Beach for the best Chicago - Valparaiso Destin-Ft Walton Beach flight prices

You are more likely to see cheaper flights to Valparaiso, Florida from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Valparaiso, Florida for around $507 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Valparaiso, Florida from Chicago for as low as $333 on momondo.

There are 3 cabin classes available to choose from on Chicago to Valparaiso, Florida 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 Valparaiso, Florida.

Sun Country Air, Southwest, and Delta are the most popular carriers operating from Chicago to Valparaiso Destin-Ft Walton Beach

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Valparaiso, Florida from Chicago according to our data. American Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Valparaiso, Florida. Keep in mind that there are 5 different airlines that fly to Valparaiso, Florida on a routine basis, so you have a few additional options to choose from.

The number of flights available between Chicago and Valparaiso, Florida is 2 per day as of August 2026. The most frequent departure time is 8:00AM, with 87% of daily flights leaving at noon.

16 flights are operational weekly from Chicago to Valparaiso, Florida as of August 2026. The most popular departure day for this route is Mon, with 19% of flights per week taking off on this day.