$94 Cheap Flights from Sioux Falls (FSD) to Chicago (MDW)

View $94 flight on Sun, Dec 7, 2025Opens in a new window

Popular airlines from Sioux Falls Regional Airport (FSD) to Chicago Midway Airport (MDW)

Cheap Flights from Sioux Falls to Chicago (FSD-MDW)

Prices were available within the past 7 days and start at $94 for one-way flights and $209 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Feb 6 - Sun, Feb 8
FSD
Sioux Falls
MDW
Chicago
$209 Roundtrip, found 8 hours ago
$209
Roundtrip
found 8 hours ago
Select Delta flight, departing Fri, Feb 6 from Sioux Falls to Chicago, returning Sun, Feb 8, priced at $209 found 8 hours ago
Frontier Airlines
Sun, Nov 2 - Thu, Nov 6
FSD
Sioux Falls
MDW
Chicago
$212 Roundtrip, found 1 day ago
$212
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Nov 2 from Sioux Falls to Chicago, returning Thu, Nov 6, priced at $212 found 1 day ago
Delta
Mon, Nov 24 - Wed, Dec 3
FSD
Sioux Falls
MDW
Chicago
$214 Roundtrip, found 1 day ago
$214
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Nov 24 from Sioux Falls to Chicago, returning Wed, Dec 3, priced at $214 found 1 day ago
Delta
Thu, Apr 23 - Fri, May 1
FSD
Sioux Falls
MDW
Chicago
$219 Roundtrip, found 3 days ago
$219
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Apr 23 from Sioux Falls to Chicago, returning Fri, May 1, priced at $219 found 3 days ago
Delta
Fri, Jan 9 - Sun, Jan 11
FSD
Sioux Falls
MDW
Chicago
$224 Roundtrip, found 19 hours ago
$224
Roundtrip
found 19 hours ago
Select Delta flight, departing Fri, Jan 9 from Sioux Falls to Chicago, returning Sun, Jan 11, priced at $224 found 19 hours ago
Delta
Wed, Nov 26 - Wed, Dec 3
FSD
Sioux Falls
MDW
Chicago
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Nov 26 from Sioux Falls to Chicago, returning Wed, Dec 3, priced at $229 found 1 day ago
Frontier Airlines
Sun, Nov 9 - Sun, Nov 16
FSD
Sioux Falls
MDW
Chicago
$232 Roundtrip, found 2 days ago
$232
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Nov 9 from Sioux Falls to Chicago, returning Sun, Nov 16, priced at $232 found 2 days ago
Frontier Airlines
Thu, Nov 6 - Sun, Nov 16
FSD
Sioux Falls
MDW
Chicago
$238 Roundtrip, found 5 days ago
$238
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Nov 6 from Sioux Falls to Chicago, returning Sun, Nov 16, priced at $238 found 5 days ago
Frontier Airlines
Thu, Nov 13 - Sun, Nov 16
FSD
Sioux Falls
MDW
Chicago
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Sioux Falls to Chicago, returning Sun, Nov 16, priced at $239 found 1 day ago
Delta
Sat, Apr 4 - Fri, Apr 24
FSD
Sioux Falls
MDW
Chicago
$244 Roundtrip, found 3 days ago
$244
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Apr 4 from Sioux Falls to Chicago, returning Fri, Apr 24, priced at $244 found 3 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $219
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $219

Frequently asked questions

How much does a flight from Sioux Falls Regional Airport (FSD) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $94 or cheap return flight from $209 from Sioux Falls Regional Airport (FSD) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Sioux Falls Regional Airport (FSD) to Midway Intl. Airport (MDW)?
February is the least expensive month to fly from FSD to MDW. Planning your trip for the off-season is often the key to better flight prices.
What is the cheapest airline that flies from Sioux Falls Regional Airport (FSD) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from FSD to MDW, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Sioux Falls Regional Airport (FSD) to Midway Intl. Airport (MDW)?
There are no daily direct flights available from Sioux Falls Regional Airport (FSD) to Midway Intl. Airport (MDW). But you can book flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be soaring above the clouds in no time at all.
What day of the week has the most flights from FSD to MDW?
Generally you'll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* However, this can vary based on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Sioux Falls Regional Airport (FSD) to Midway Intl. Airport (MDW)?
Select a flight from Sioux Falls Regional Airport (FSD) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the likelihood of delays. Departures after this hour are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Sioux Falls Regional Airport (FSD)?
If you're boarding a direct flight from Sioux Falls Regional Airport (FSD) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Sioux Falls Regional Airport (FSD) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from FSD to MDW are typically more expensive. To lock in the best prices, start looking for flights well in advance. That said, if you're flexible with your travel dates, you may score a cheap ticket right before your trip.
Is it cheaper to book a FSD to MDW flight and hotel package?
You'll generally save money by securing a FSD to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. After selecting your preferred accommodations and flights, consider adding extras such as car rentals, tours and activities.
Can I cancel or change the date of my flight from Sioux Falls Regional Airport (FSD) to Midway Intl. Airport (MDW)?
It's generally possible to cancel or reschedule your FSD to MDW flight. However, if it's been more than 24 hours since booking, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
Sioux Falls Regional
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$208
Distance
472 mi

Book with confidence

Sioux Falls to Chicago Flights

The cheapest times to fly from Sioux Falls to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Sioux Falls to Chicago are during the month of February. You can find some of the cheapest flights from Sioux Falls to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Sioux Falls to Chicago

Sunday is one of the best days to book for cheap flights from Sioux Falls to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Sioux Falls to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Sioux Falls to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $94 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Sioux Falls to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Sioux Falls to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Sioux Falls to Chicago Flights

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*Available to One Key members.