Cheap Flights from Chicago to South Dakota from $340 Return

Flight deals from Chicago to South Dakota

Looking for a cheap last-minute deal or the best return flight from Chicago to South Dakota? If you want to travel next month, return fares start from $393. Find the lowest prices on one-way and return tickets right here.

Rapid City.$340 per passenger.Departing Wed, 27 May, returning Wed, 10 Jun.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Wed, 27 May, arriving in Rapid City Regional.Inbound indirect flight with United, departs from Rapid City Regional on Wed, 10 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $340, select.

Sioux Falls.$420 per passenger.Departing Fri, 10 Jul, returning Mon, 13 Jul.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 10 Jul, arriving in Sioux Falls.Inbound direct flight with United departs from Sioux Falls on Mon, 13 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $420, select.

Watertown.$531 per passenger.Departing Fri, 22 May, returning Mon, 25 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 22 May, arriving in Watertown.Inbound indirect flight with Delta, departs from Watertown on Mon, 25 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $531, select.

Aberdeen.$683 per passenger.Departing Tue, 19 Jan, returning Sat, 23 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 19 Jan, arriving in Aberdeen.Inbound indirect flight with Delta, departs from Aberdeen on Sat, 23 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From $683, select.

Pierre.$1,041 per passenger.Departing Wed, 6 May, returning Sun, 10 May.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Wed, 6 May, arriving in Pierre.Inbound indirect flight with United, departs from Pierre on Sun, 10 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,041, select.

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Flying from Chicago to South Dakota

Arm yourself with these facts on the fly.

Cheapest flight found	$340
Cheapest month to fly	May
Average flight time	2 hrs, 17 mins
Cheapest airport to fly from	Chicago O'Hare International
Most popular airline	American Airlines

How to find cheap flights from Chicago to South Dakota

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago to South Dakota. Other savvy travellers recently found return flights from $340 and one-way tickets from $128 one-way. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago O'Hare International into Rapid City Regional

At the moment, the lowest priced flight tickets to South Dakota are from Chicago O'Hare International Airport to Rapid City Regional Airport.

Fly in May

We crunched the flight calendar and found the cheapest time to fly from Chicago to South Dakota is currently May.

Flex your dates for the best rates

If you’re flexible on your departure dates, you can use Skyscanner's whole month tool to find the cheapest day of the year to fly from Chicago to anywhere you choose in South Dakota.

Watch as fares rise and fall

With Price Alerts, we'll let you know when flight prices from Chicago to South Dakota go up or down so you can book when the time is just right.

Relax – these are fee-free flight tickets

With us, there are no added fees – the South Dakota to South Dakota flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

What's the average Chicago to South Dakota flight price?

We looked at all of the upcoming return flights from Chicago to South Dakota we could find over the next 12 months. It looks like $340 is the best price. This is good, compared to the average South Dakota ticket price of $603.

What is the cheapest month to fly from Chicago to South Dakota?

The cheapest month to fly from Chicago to Aberdeen Airport is usually January. The cheapest month to fly from Chicago to Sioux Falls Airport is usually July. The cheapest month to fly from Chicago to Pierre Airport is usually May. And the cheapest month to fly from Chicago to Rapid City Regional Airport is usually May.

Which upcoming date is cheapest to fly from Chicago to South Dakota on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to South Dakota on Wednesday, 27 May 2026.

Are there any direct flights from Chicago to South Dakota?

Chicago O'Hare International Airport offers direct flights to South Dakota.

If I'm flying from Chicago, where in South Dakota is cheapest to fly into?

If you're flying from Chicago, the cheapest city in South Dakota to fly into is Rapid City. The cheapest airport serving Rapid City at the moment is Rapid City Regional.