Cheap flights from South Dakota to Chicago from $108

The month of September is, on average, the cheapest month to fly to Chicago from South Dakota, with most prices found around $244. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from South Dakota to Chicago during January average around $249.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $402. 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 South Dakota to Chicago for around $630.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from South Dakota to Chicago during this time can be as low as $374. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $486.

Fly from Rapid City to Chicago O'Hare Intl for the best South Dakota - Chicago flight prices

You are more likely to see cheaper flights to Chicago from South Dakota when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $297 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from South Dakota for as low as $195 on momondo.

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.

As of March 2026, there are 10 flights per day flying from South Dakota to Chicago. The most common time of day flights depart is 2:00PM, with 46% of flights taking off in the afternoon.

As of March 2026, there are 70 flights per week flying from South Dakota to Chicago. The most common day of the week flights depart is Sat, with 21% of flights taking off on this day.