Cheap flights from Sioux Falls to Chicago from $152

The month of January is, on average, the cheapest month to fly to Chicago from Sioux Falls, with most prices found around $242. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Sioux Falls to Chicago during February average around $296.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $433. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Sioux Falls to Chicago for around $749.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Sioux Falls to Chicago during this time can be as low as $402. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $530.

Fly from Sioux Falls Joe Foss Field to Chicago O'Hare Intl for the best Sioux Falls Joe Foss Field - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Sioux Falls when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $384 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Sioux Falls for as low as $255 on momondo.

There are 4 cabin classes available to choose from on Sioux Falls to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 20% on your flight if you consider stops on a Sioux Falls to Chicago flight.

As of November 2026, prices for Sioux Falls to Chicago flights are approximately 215% more expensive when compared to flights at the same time last year.

As of November 2026, 14 flights take off from Sioux Falls and land in Chicago each day. The most common flight departure time for this route is 3:00PM, with 40% of daily flights taking off in the afternoon.

As of November 2026, 101 flights take off from Sioux Falls and land in Chicago each week. The most common flight departure day for this route is Mon, with 19% of weekly flights taking off on this day.