Cheap flights from Chicago to South Dakota from $126

The month of May is, on average, the cheapest month to fly to South Dakota from Chicago, with most prices found around $168. If you aren’t able to travel to South Dakota during the month of May, then flying in December is also cheap. Prices for this month can be found on momondo for an average of $189.

The cheapest day to depart from Chicago to South Dakota is on a Wednesday. Travelers who choose to depart for South Dakota on a Wednesday will often find tickets for as low as $249. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $470. These prices are subject to change though, so be sure to set up a Price Alert for flights to South Dakota.

The cheapest time of day to fly to South Dakota is in the evening when flights can be purchased for as low as $303. At noon is when there is more demand to fly to South Dakota, so prices are often more expensive at around $374 per ticket.

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

There are 3 cabin classes available to choose from on Chicago to South Dakota 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 18% on your flight if you consider stops on a Chicago to South Dakota flight.

As of June 2026, there are 21 flights per day flying from Chicago to South Dakota. The most common time of day flights depart is 8:00AM, with 39% of flights taking off at noon.

150 flights are operational weekly from Chicago to South Dakota as of June 2026. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.