Cheap flights from South Dakota to Chicago from $101

The month of November is, on average, the cheapest month to fly to Chicago from South Dakota, with most prices found around $246. If you’re not able to fly to Chicago in November, then January is your next best option. Flight prices from South Dakota to Chicago during January average around $258.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $457. 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 South Dakota to Chicago for around $609.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from South Dakota to Chicago during this time can be as low as $475. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $497.

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

There are 4 cabin classes available to choose from on South Dakota 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 5% on your flight if you consider stops on a South Dakota to Chicago flight.

As of August 2026, there are 21 flights per day flying from South Dakota to Chicago. The most common time of day flights depart is 12:00PM, with 61% of flights taking off in the afternoon.

As of August 2026, there are 148 flights per week flying from South Dakota to Chicago. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.