Cheap Flights from Sioux Falls SD to Chicago IL from $276

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Flight deals from Sioux Falls to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Sioux Falls Airport to Chicago? If you want to travel next month, round-trip fares start from $276. Find the lowest prices on one-way and round-trip tickets right here.

Chicago.$276 per passenger.Departing Fri, Feb 12, returning Fri, Feb 26.Round-trip flight with United.Outbound direct flight with United departing from Sioux Falls on Fri, Feb 12, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Fri, Feb 26, arriving in Sioux Falls.Price includes taxes and charges.From $276, select.

Chicago.$276 per passenger.Departing Fri, Apr 9, returning Fri, Apr 23.Round-trip flight with United.Outbound direct flight with United departing from Sioux Falls on Fri, Apr 9, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Fri, Apr 23, arriving in Sioux Falls.Price includes taxes and charges.From $276, select.

Chicago.$276 per passenger.Departing Fri, Dec 11, returning Fri, Dec 25.Round-trip flight with United.Outbound direct flight with United departing from Sioux Falls on Fri, Dec 11, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Fri, Dec 25, arriving in Sioux Falls.Price includes taxes and charges.From $276, select.

Chicago.$276 per passenger.Departing Tue, Nov 24, returning Fri, Nov 27.Round-trip flight with United.Outbound direct flight with United departing from Sioux Falls on Tue, Nov 24, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Fri, Nov 27, arriving in Sioux Falls.Price includes taxes and charges.From $276, select.

Chicago.$276 per passenger.Departing Sat, Oct 24, returning Sat, Oct 31.Round-trip flight with American Airlines.Outbound direct flight with American Airlines departing from Sioux Falls on Sat, Oct 24, arriving in Chicago O'Hare International.Inbound direct flight with American Airlines departing from Chicago O'Hare International on Sat, Oct 31, arriving in Sioux Falls.Price includes taxes and charges.From $276, select.

Chicago.$289 per passenger.Departing Fri, Jun 11, returning Fri, Jun 25.Round-trip flight with United.Outbound direct flight with United departing from Sioux Falls on Fri, Jun 11, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Fri, Jun 25, arriving in Sioux Falls.Price includes taxes and charges.From $289, select.

Chicago.$289 per passenger.Departing Fri, May 14, returning Fri, May 28.Round-trip flight with United.Outbound direct flight with United departing from Sioux Falls on Fri, May 14, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Fri, May 28, arriving in Sioux Falls.Price includes taxes and charges.From $289, select.

Chicago.$296 per passenger.Departing Fri, Jan 8, returning Fri, Jan 22.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Sioux Falls on Fri, Jan 8, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Fri, Jan 22, arriving in Sioux Falls.Price includes taxes and charges.From $296, select.

Chicago.$296 per passenger.Departing Thu, Jan 7, returning Thu, Jan 14.Round-trip flight with United.Outbound direct flight with United departing from Sioux Falls on Thu, Jan 7, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Thu, Jan 14, arriving in Sioux Falls.Price includes taxes and charges.From $296, select.

Chicago.$297 per passenger.Departing Fri, Oct 30, returning Mon, Nov 2.Round-trip flight with United.Outbound direct flight with United departing from Sioux Falls on Fri, Oct 30, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Mon, Nov 2, arriving in Sioux Falls.Price includes taxes and charges.From $297, select.

Chicago.$306 per passenger.Departing Sat, Sep 26, returning Tue, Sep 29.Round-trip flight with United.Outbound direct flight with United departing from Sioux Falls on Sat, Sep 26, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Tue, Sep 29, arriving in Sioux Falls.Price includes taxes and charges.From $306, select.

Chicago.$310 per passenger.Departing Fri, Nov 27, returning Tue, Dec 15.Round-trip flight with United.Outbound direct flight with United departing from Sioux Falls on Fri, Nov 27, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Tue, Dec 15, arriving in Sioux Falls.Price includes taxes and charges.From $310, select.

Chicago.$317 per passenger.Departing Sun, Mar 7, returning Sun, Mar 14.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Sioux Falls on Sun, Mar 7, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departing from Chicago O'Hare International on Sun, Mar 14, arriving in Sioux Falls.Price includes taxes and charges.From $317, select.

Chicago.$348 per passenger.Departing Wed, Sep 30, returning Sun, Oct 4.Round-trip flight with United.Outbound direct flight with United departing from Sioux Falls on Wed, Sep 30, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Sun, Oct 4, arriving in Sioux Falls.Price includes taxes and charges.From $348, select.

Chicago.$368 per passenger.Departing Fri, Mar 12, returning Fri, Mar 26.Round-trip flight with United.Outbound direct flight with United departing from Sioux Falls on Fri, Mar 12, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Fri, Mar 26, arriving in Sioux Falls.Price includes taxes and charges.From $368, select.

Chicago.$381 per passenger.Departing Thu, Dec 17, returning Mon, Jan 4.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Sioux Falls on Thu, Dec 17, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Mon, Jan 4, arriving in Sioux Falls.Price includes taxes and charges.From $381, 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 October.

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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	$276
Cheapest month to fly	October
Average flight time	2 hrs, 1 min
Most popular airline	American Airlines
Average flights per week	476

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

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.

How much are round-trip flights from Sioux Falls to Chicago?

The best price we found for a round-trip flight from Sioux Falls to Chicago is $276. 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?

2 hours and 1 minute is the average flight time from Sioux Falls to Chicago.

Which airlines fly direct from Sioux Falls to Chicago?

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

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

There are 238 flights per week flying from Sioux Falls to Chicago, as of September 2026.

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

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

What's the cheapest airport to fly to in Chicago?

If you're flying from Sioux Falls Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the center of Chicago. We've found flights to this airport from $276.

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 Saturday, October 24, 2026.

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

Yes – the average flight time is 2 hours and 1 minute.

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 September, the average temperature is usually around 20°C. July is typically the warmest month in Chicago, when it usually averages around 27°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -5°C. The rainiest month is June.

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

Currently, American Airlines 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 traveling 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.
Traveling 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 cab, you'll cover the 5 kilometers 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 $125. The cheapest price for a return flight is $276. 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 kilometers from central Chicago. If you're grabbing a cab or a ride-share, the drive takes roughly 30 minutes.
Traveling to the center 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 kilometers 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 cozy 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 kilometers from central Chicago. It'll take you about 1 hour 40 minutes to reach the city center by ride-share or cab 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 (61ºF) and 28ºC (82ºF). 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 traveling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) 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 kilometers southeast to Columbus to check off its leading sights. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theater, there's plenty to keep you busy.
Around 257 kilometers 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.