Cheap Flights from Sioux Falls to Chicago from $423

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Flight deals from Sioux Falls to Chicago

Looking for a cheap last-minute deal or the best return flight from Sioux Falls Airport to Chicago? If you want to travel next month, return fares start from $425. Find the lowest prices on one-way and return tickets right here.

Chicago.$423 per passenger.Departing Tue, 5 Jan, returning Tue, 19 Jan.Return flight with United.Outbound direct flight with United departs from Sioux Falls on Tue, 5 Jan, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 19 Jan, arriving in Sioux Falls.Price includes taxes and charges.From $423, select.

Chicago.$424 per passenger.Departing Sat, 5 Sep, returning Mon, 7 Sep.Return flight with United.Outbound direct flight with United departs from Sioux Falls on Sat, 5 Sep, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Mon, 7 Sep, arriving in Sioux Falls.Price includes taxes and charges.From $424, select.

Chicago.$425 per passenger.Departing Fri, 12 Feb, returning Sun, 14 Feb.Return flight with United.Outbound direct flight with United departs from Sioux Falls on Fri, 12 Feb, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 14 Feb, arriving in Sioux Falls.Price includes taxes and charges.From $425, select.

Chicago.$425 per passenger.Departing Wed, 1 Jul, returning Fri, 31 Jul.Return flight with United.Outbound direct flight with United departs from Sioux Falls on Wed, 1 Jul, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Fri, 31 Jul, arriving in Sioux Falls.Price includes taxes and charges.From $425, select.

Chicago.$425 per passenger.Departing Wed, 21 Oct, returning Wed, 28 Oct.Return flight with United.Outbound direct flight with United departs from Sioux Falls on Wed, 21 Oct, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Wed, 28 Oct, arriving in Sioux Falls.Price includes taxes and charges.From $425, select.

Chicago.$425 per passenger.Departing Tue, 27 Oct, returning Tue, 3 Nov.Return flight with United.Outbound direct flight with United departs from Sioux Falls on Tue, 27 Oct, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 3 Nov, arriving in Sioux Falls.Price includes taxes and charges.From $425, select.

Chicago.$428 per passenger.Departing Mon, 20 Jul, returning Fri, 14 Aug.Return flight with United.Outbound direct flight with United departs from Sioux Falls on Mon, 20 Jul, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Fri, 14 Aug, arriving in Sioux Falls.Price includes taxes and charges.From $428, select.

Chicago.$439 per passenger.Departing Mon, 2 Nov, returning Mon, 9 Nov.Return flight with United.Outbound direct flight with United departs from Sioux Falls on Mon, 2 Nov, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Mon, 9 Nov, arriving in Sioux Falls.Price includes taxes and charges.From $439, select.

Chicago.$442 per passenger.Departing Fri, 7 Aug, returning Sun, 9 Aug.Return flight with United.Outbound direct flight with United departs from Sioux Falls on Fri, 7 Aug, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 9 Aug, arriving in Sioux Falls.Price includes taxes and charges.From $442, select.

Chicago.$470 per passenger.Departing Sat, 20 Jun, returning Sat, 27 Jun.Return flight with United.Outbound direct flight with United departs from Sioux Falls on Sat, 20 Jun, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 27 Jun, arriving in Sioux Falls.Price includes taxes and charges.From $470, select.

Chicago.$482 per passenger.Departing Mon, 28 Sep, returning Mon, 5 Oct.Return flight with United.Outbound direct flight with United departs from Sioux Falls on Mon, 28 Sep, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Mon, 5 Oct, arriving in Sioux Falls.Price includes taxes and charges.From $482, select.

Chicago.$854 per passenger.Departing Mon, 29 Jun, returning Wed, 1 Jul.Return flight with United.Outbound direct flight with United departs from Sioux Falls on Mon, 29 Jun, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Wed, 1 Jul, arriving in Sioux Falls.Price includes taxes and charges.From $854, select.

Find the cheapest month to fly from Sioux Falls to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Sioux Falls to Chicago flights are currently cheapest in January.

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Direct flights from Sioux Falls to Chicago

Alternative Sioux Falls to Chicago routes

Looking for the cheapest, fastest or easiest route from Sioux Falls to Chicago? You could fly into the following airports instead.

Sioux Falls to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$423
Cheapest month to fly	January
Average flight time	1 hr, 58 mins
Most popular airline	American Airlines
Average flights per week	210

Finding cheap flights from Sioux Falls to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are return flights from Sioux Falls to Chicago?

The best price we found for a return flight from Sioux Falls to Chicago is $423. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from Sioux Falls to Chicago?

1 hour and 58 minutes is the average flight time from Sioux Falls to Chicago.

Which airlines fly direct from Sioux Falls to Chicago?

American Airlines, SkyWest Airlines and Alaska Airlines fly direct from Sioux Falls to Chicago.

How many flights are there a week from Sioux Falls to Chicago?

As of June 2026, there are 210 flights per week flying from Sioux Falls to Chicago.

When is the cheapest time to fly from Sioux Falls to Chicago?

The cheapest month to fly from Sioux Falls to Chicago is usually January.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Sioux Falls Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $423.

Which upcoming date is cheapest to fly from Sioux Falls Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Sioux Falls Airport to Chicago on Tuesday, 5 January 2027.

Can I get a direct flight from Sioux Falls Airport to Chicago?

Yes – the average flight time is 1 hour and 58 minutes.

How can I get the best flight deal from Sioux Falls Airport to Chicago?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Chicago?

In June, the average temperature is usually around 19°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly from Sioux Falls Airport to Chicago with?

Currently, United offers the cheapest flight tickets to Chicago.

Flying from Sioux Falls Regional Airport (FSD) to Chicago: what you need to know

Around 1 hour 50 minutes is how long you can expect to be travelling on a direct flight from Sioux Falls Regional Airport to Chicago.
Chicago and Sioux Falls (where Sioux Falls Regional Airport is located) are both in the UTC-6 timezone. This means you won't have to change your watch on arrival.
With 48 weekly flights between the two airports, Sioux Falls Regional Airport (FSD) to Chicago O'Hare International Airport (ORD) is the busiest route. American Airlines operates the earliest flight at 05:15. If you'd like to make the most of your day before flying, the last departure from FSD to ORD is with United Airlines at 18:38.
To avoid missing your FSD to Chicago flight, leave plenty of time to navigate the airport and find your gate. Arriving two hours before international departures and an hour before domestic flights is the general travel rule.
Travelling during a peak month like March? School holidays and other high seasons can mean longer lines at check-in and security. Play things extra safe and arrive up to four hours ahead of international flights and two hours before a domestic departure.
Begin your journey at FSD and travel nonstop to Chicago O'Hare International Airport (ORD). That's where you can expect to land when searching for Sioux Falls Regional Airport to Chicago tickets.
Look out for offers from United Airlines. This airline operates direct flights from Sioux Falls Regional Airport to Chicago.
The journey from central Sioux Falls to FSD takes around 35 minutes on public transport. If you ride-share, drive or take a taxi, you'll cover the 5 kilometres in 15 minutes or so, depending on traffic.
Want an easy start to your trip? Stay near FSD. Whether you have an early flight from Sioux Falls Regional Airport to Chicago or just don't like being rushed, these hotels are just the thing:
70% of flights that take off from Sioux Falls Regional Airport make it to their destination on schedule.
FSD's address is 2801 Jaycee Lane.

How to find the cheapest flights from Sioux Falls Regional Airport (FSD) to Chicago

The best price we've seen for a one-way Sioux Falls Regional Airport to Chicago flight is $238. The cheapest price for a return flight is $423. Keep in mind fares can change due to demand at the time of booking.
Book seven months before flying. Pricing trends suggest that this is the ideal window for finding cheap flights from FSD to Chicago.
December is the best month for picking up a fantastic deal on Sioux Falls Regional Airport to Chicago tickets. If you want to travel during a different time of year, the 'Whole month' tool will show you the lowest prices for every month.
Picking up a cheap flight from FSD to Chicago is easy with Price Alerts. All you need to do is create one of these automatic notifications and we'll get in touch when there's a better deal.
Snag an affordable flight from Sioux Falls Regional Airport to Chicago with the help of our filters. Choose your ideal departure time, duration and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

Chicago O'Hare International Airport (ORD) is around 27 kilometres from central Chicago. If you're grabbing a taxi or a ride-share, the drive takes roughly 30 minutes.
Travelling to the centre on public transport takes around 45 minutes.
Consider booking a hotel near ORD if you're coming in on a late flight from Sioux Falls Regional Airport to Chicago. Check in to one of these options and make your first night all about catching up on rest:
For the best deal, book your ride from Chicago O'Hare International Airport around four weeks ahead of your flight from FSD to Chicago.
The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Central Chicago is located around 16 kilometres from Chicago Midway International Airport (MDW). Once your flight from Sioux Falls Regional Airport to Chicago has touched down and you've made your way out of the airport, expect a drive of about 25 minutes.
Public transport will get you there in about 30 minutes.
You'll find some great places to call home for the night near MDW. Settle in and get cosy after your FSD to Chicago flight at any of these perfectly located options:
Get exactly what you want. Securing your ride from MDW four weeks ahead of time often means more savings and a wider choice of vehicles.
You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Chicago Rockford International Airport (RFD) is about 145 kilometres from central Chicago. It'll take you about 1 hour 40 minutes to reach the city centre by ride-share or taxi after your flight from Sioux Falls Regional Airport to Chicago.
If you go by public transport, the journey time is about 2 hours.
Enjoy an unhurried start to your break by staying at a hotel near RFD after your FSD to Chicago flight. Rest up after a long day of travel or simply take a moment to get your footing in a new city at:
If you're looking for a specific model or make, booking early gives you a better shot at getting your first choice. Secure your ride from RFD a couple of weeks ahead of your flight from Sioux Falls Regional Airport to Chicago.
The street address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

January is the quietest month for flights from Sioux Falls Regional Airport to Chicago, while July is the most popular. Find the ideal time to visit Chicago based on whether you prefer a bustling atmosphere or a more laid-back vibe.
The warmest month in Chicago is July, with temperatures ranging between 16ºC and 28ºC. Lock in your Sioux Falls Regional Airport to Chicago plane ticket then if that's your idea of comfortable weather.
Look for cheap tickets from FSD to Chicago in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

More about Chicago

After booking your flight from Sioux Falls Regional Airport to Chicago, find a hotel that keeps you close to what you want to see. Make one of these accommodation options your base for exploring Chicago:
Art Institute of Chicago and Millennium Park are just two of the top attractions to add to your Chicago itinerary. Keep the momentum going by heading to Willis Tower.

Explore more of the United States

You've visited Chicago, now it's time to discover other corners of the United States. Travel around 451 kilometres southeast to Columbus to check off its leading sights. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, there's plenty to keep you busy.
Around 257 kilometres southeast of Chicago, Indianapolis is another essential stop in the United States. No visit is complete without checking out Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.