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$227 Cheap Flights from Sioux Falls (FSD) to Chicago (MDW)

View $227 flight on Thu, Oct 1, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $227 for one-way flights and $279 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Feb 26 - Tue, Mar 9
FSD
Sioux Falls
MDW
Chicago
$279 Roundtrip, found 3 hours ago
$279
Roundtrip
found 3 hours ago
Select Delta flight, departing Fri, Feb 26 from Sioux Falls to Chicago, returning Tue, Mar 9, priced at $279 found 3 hours ago
Delta
Fri, Feb 26 - Tue, Mar 9
FSD
Sioux Falls
MDW
Chicago
$294 Roundtrip, found 3 hours ago
$294
Roundtrip
found 3 hours ago
Select Delta flight, departing Fri, Feb 26 from Sioux Falls to Chicago, returning Tue, Mar 9, priced at $294 found 3 hours ago
Delta
Wed, Sep 2 - Sat, Sep 5
FSD
Sioux Falls
MDW
Chicago
$309 Roundtrip, found 3 hours ago
$309
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Sep 2 from Sioux Falls to Chicago, returning Sat, Sep 5, priced at $309 found 3 hours ago
Delta
Sat, Oct 3 - Tue, Oct 6
FSD
Sioux Falls
MDW
Chicago
$312 Roundtrip, found 16 hours ago
$312
Roundtrip
found 16 hours ago
Select Delta flight, departing Sat, Oct 3 from Sioux Falls to Chicago, returning Tue, Oct 6, priced at $312 found 16 hours ago
Delta
Fri, Feb 26 - Tue, Mar 9
FSD
Sioux Falls
MDW
Chicago
$324 Roundtrip, found 3 hours ago
$324
Roundtrip
found 3 hours ago
Select Delta flight, departing Fri, Feb 26 from Sioux Falls to Chicago, returning Tue, Mar 9, priced at $324 found 3 hours ago
Delta
Wed, Oct 21 - Thu, Oct 29
FSD
Sioux Falls
MDW
Chicago
$327 Roundtrip, found 22 hours ago
$327
Roundtrip
found 22 hours ago
Select Delta flight, departing Wed, Oct 21 from Sioux Falls to Chicago, returning Thu, Oct 29, priced at $327 found 22 hours ago
Delta
Fri, Feb 26 - Tue, Mar 9
FSD
Sioux Falls
MDW
Chicago
$339 Roundtrip, found 3 hours ago
$339
Roundtrip
found 3 hours ago
Select Delta flight, departing Fri, Feb 26 from Sioux Falls to Chicago, returning Tue, Mar 9, priced at $339 found 3 hours ago
Delta
Sun, Sep 20 - Sat, Sep 26
FSD
Sioux Falls
MDW
Chicago
$342 Roundtrip, found 10 hours ago
$342
Roundtrip
found 10 hours ago
Select Delta flight, departing Sun, Sep 20 from Sioux Falls to Chicago, returning Sat, Sep 26, priced at $342 found 10 hours ago
Delta
Fri, Oct 2 - Tue, Oct 6
FSD
Sioux Falls
MDW
Chicago
$345 Roundtrip, just found
$345
Roundtrip
just found
Select Delta flight, departing Fri, Oct 2 from Sioux Falls to Chicago, returning Tue, Oct 6, priced at $345 just found
Delta
Fri, Feb 26 - Tue, Mar 9
FSD
Sioux Falls
MDW
Chicago
$349 Roundtrip, found 3 hours ago
$349
Roundtrip
found 3 hours ago
Select Delta flight, departing Fri, Feb 26 from Sioux Falls to Chicago, returning Tue, Mar 9, priced at $349 found 3 hours 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 $657
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $657

What you need to know for your flight from Sioux Falls Regional to Midway Intl.

Sioux Falls (FSD) to Chicago (MDW) at a glance

Travel from Sioux Falls (FSD) to Chicago (MDW) with a choice of airlines on this convenient domestic short-haul route. You can compare options for flights from Sioux Falls to Chicago, whether you prefer full-service or budget carriers, to discover the itinerary that aligns with your budget and schedule. As you plan your visit to explore the iconic sights and vibrant neighborhoods of Chicago, be sure to check out the essential details for your flight from Sioux Falls Regional Airport to Midway International Airport.

  • Fastest flight duration: around 3 hours in-flight, plus roughly 1h 30m layover with one stop
  • Route distance: roughly 450 miles (725 km)
  • Flights per week: around 7 departures on average
  • Typical fares (one-way): economy tickets often range from $100–$305, depending on seasonality and how far ahead you book

Flights from Sioux Falls Regional Airport (FSD) to Midway International Airport (MDW)

Based on the latest traveler bookings, here are the top airlines flying from Sioux Falls to Chicago, commonly preferred for their one-stop options. Popular layover points include Minneapolis-St. Paul International Airport (MSP) with an average layover time of about 1 hour and 30 minutes, and Denver International Airport (DEN) with a layover of around 1 hour. These choices allow you to customize your itinerary based on price, total travel time, and cabin class for an optimal travel experience.

  • Delta: This full-service airline provides comprehensive one-stop service, with one-way ticket prices generally falling between $100 and $340. Delta operates about 76% of flights on this route, featuring an in-flight duration of 3 hours and a total travel time of approximately 4 hours and 30 minutes, including layover.
  • Frontier Airlines: As a budget-friendly carrier, Frontier Airlines offers one-stop service, with one-way fares typically ranging from $115 to $165. This airline represents around 24% of departures on this route, boasting a flight time of 3 hours and a total journey duration of roughly 4 hours and 30 minutes, factoring in a layover.

Alternative route from Sioux Falls (FSD) to Chicago (MDW)

  • Sioux Falls to Chicago (FSD-ORD): O'Hare International Airport (ORD) is located roughly 16 miles from Midway International Airport (MDW). One-way economy ticket prices for this journey generally fall between $85 and $335, influenced by the season and how far in advance you book. Travelers can choose from both non-stop and one-stop flight options. Major airlines serving this route include United and American Airlines. Additionally, first class service is available for those seeking a more premium experience.

How to find the best prices for flights from Sioux Falls (FSD) to Chicago (MDW)

Getting some of the best deals on flights from Sioux Falls to Chicago is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are typically available when booking 2-8 weeks in advance, although most travelers tend to book within 2 weeks. Morning departures (5 AM-12 PM) usually offer lower prices, while afternoon flights (12 PM-6 PM) are more popular. Additionally, flying on Saturday generally results in cheaper fares, even though Sunday is the most sought-after travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Midway International Airport from Sioux Falls Regional Airport

Chicago welcomes travelers from Sioux Falls with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
  • Car rental: Renting a car from Midway International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Midway International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Midway International Airport, Midway Station (a metro station) is located about 0.2 miles away on foot, while Chicago Ashburn Station (a train station) is approximately 4.1 miles from the airport by car. Additionally, Lyons Seaport (a seaport) sits around 7.2 miles away by car, providing various transport options for travelers.

Frequently asked questions

How much does a flight from Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $227 and cheap return flights from $279 Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights generally range between $352 and $714, and roundtrip flights usually range from $473 to $1475. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from FSD to MDW is February when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.)?
Enter FSD to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.)?
Delta is one of the cheapest airlines offering connecting flights from Sioux Falls Regional (FSD) to Midway Intl. (MDW), with round-trip tickets starting from around $368. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.)?
Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from FSD to MDW. To compare more early flights, use the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Sioux Falls (FSD) to Chicago (MDW) are in the early morning, from 3am to 6am. About 48% of passengers prefer this time window. Delta Airlines is a major carrier offering flights during this window. This timing is favored as it allows travelers to arrive in Chicago early and make the most of their day.
How long does it take to fly from Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.)?
Flights from FSD to MDW with one stop typically take around 5 hours, covering approximately 473 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the FSD to MDW route with Delta Air Lines.
How do I earn miles on a Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Sioux Falls Regional (FSD)?
From Sioux Falls Regional (FSD), you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Dallas-Fort Worth Intl. (DFW), Minneapolis - St. Paul Intl. (MSP), Denver Intl. (DEN) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Sioux Falls, SD (FSD-Sioux Falls Regional) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Sioux Falls Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$278
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 2026. You can also book with separate airlines for your outbound and return journeys, from $227 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

*Flight schedules are subject to change.

*Available to One Key members.

 

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