$139 Cheap Flights from Springfield (SGF) to Chicago (MDW)

View $139 flight on Sun, Nov 9, 2025Opens in a new window

Popular airlines from Springfield-Branson National Airport (SGF) to Chicago Midway Airport (MDW)

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Cheap Flights from Springfield to Chicago (SGF-MDW)

Prices were available within the past 7 days and start at $139 for one-way flights and $209 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Nov 11 - Tue, Nov 18
SGF
Springfield
MDW
Chicago
$209 Roundtrip, found 3 hours ago
$209
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Nov 11 from Springfield to Chicago, returning Tue, Nov 18, priced at $209 found 3 hours ago
Delta
Tue, Sep 30 - Tue, Oct 7
SGF
Springfield
MDW
Chicago
$214 Roundtrip, found 2 days ago
$214
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 30 from Springfield to Chicago, returning Tue, Oct 7, priced at $214 found 2 days ago
Delta
Wed, Nov 5 - Wed, Nov 12
SGF
Springfield
MDW
Chicago
$232 Roundtrip, found 9 hours ago
$232
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Nov 5 from Springfield to Chicago, returning Wed, Nov 12, priced at $232 found 9 hours ago
Delta
Tue, Mar 24 - Wed, Apr 8
SGF
Springfield
MDW
Chicago
$237 Roundtrip, found 6 hours ago
$237
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Mar 24 from Springfield to Chicago, returning Wed, Apr 8, priced at $237 found 6 hours ago
Delta
Tue, Nov 11 - Thu, Nov 20
SGF
Springfield
MDW
Chicago
$239 Roundtrip, found 3 hours ago
$239
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Nov 11 from Springfield to Chicago, returning Thu, Nov 20, priced at $239 found 3 hours ago
Delta
Tue, Sep 30 - Sat, Oct 18
SGF
Springfield
MDW
Chicago
$242 Roundtrip, found 2 days ago
$242
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 30 from Springfield to Chicago, returning Sat, Oct 18, priced at $242 found 2 days ago
Delta
Mon, Sep 22 - Tue, Sep 30
SGF
Springfield
MDW
Chicago
$244 Roundtrip, found 5 days ago
$244
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Sep 22 from Springfield to Chicago, returning Tue, Sep 30, priced at $244 found 5 days ago
Delta
Sat, Sep 27 - Tue, Sep 30
SGF
Springfield
MDW
Chicago
$249 Roundtrip, found 2 days ago
$249
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep 27 from Springfield to Chicago, returning Tue, Sep 30, priced at $249 found 2 days ago
Delta
Wed, Dec 10 - Sun, Dec 14
SGF
Springfield
MDW
Chicago
$260 Roundtrip, found 2 days ago
$260
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Dec 10 from Springfield to Chicago, returning Sun, Dec 14, priced at $260 found 2 days ago
Delta
Sat, Nov 15 - Mon, Nov 17
SGF
Springfield
MDW
Chicago
$267 Roundtrip, found 2 days ago
$267
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Nov 15 from Springfield to Chicago, returning Mon, Nov 17, priced at $267 found 2 days ago

Find the cheapest month to fly from Springfield (SGF) to Chicago (MDW)

January is typically the cheapest month to fly

From $208 - $679 per traveler.

Frequently asked questions

How much does a flight from Springfield-Branson National Airport (SGF) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $139 or cheap return flight from $209 from Springfield-Branson National Airport (SGF) 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 Springfield-Branson National Airport (SGF) to Midway Intl. Airport (MDW)?
Traveling in November may help you find better deals, as it's the cheapest month for flights between SGF and MDW. You'll usually find the lowest fares during the off-season.
What is the cheapest airline that flies from Springfield-Branson National Airport (SGF) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, travel time and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest SGF to MDW flight.
How many flights per day from Springfield-Branson National Airport (SGF) to Midway Intl. Airport (MDW)?
There aren't any daily nonstop flights available from Springfield-Branson National Airport (SGF) to Midway Intl. Airport (MDW). But you can book flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be soaring above the clouds in no time.
What day of the week has the most flights from SGF to MDW?
Usually you'll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can vary depending on the time of year, carrier 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 Springfield-Branson National Airport (SGF) to Midway Intl. Airport (MDW)?
To touch down at Midway Intl. Airport (MDW) without delays, opt for a flight that takes off from Springfield-Branson National Airport (SGF) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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 Springfield-Branson National Airport (SGF)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Springfield-Branson National Airport (SGF). Consider the options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Springfield-Branson National Airport (SGF) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from SGF to MDW shortly before your trip is usually more expensive. But if there's some wiggle room with your travel times and dates, you could grab a cheap last-minute fare.
Is it cheaper to book a SGF to MDW flight and hotel package?
You can save money by booking a SGF 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 simple to manage everything in one place. After choosing your ideal accommodations and flights, you can add extras such as tours, car rentals and activities.
Can I cancel or change the date of my flight from Springfield-Branson National Airport (SGF) to Midway Intl. Airport (MDW)?
It's usually possible to reschedule or cancel your SGF 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 allowed and if any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Travel information

Origin airport
Springfield-Branson National
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$208
Distance
434 mi

Book with confidence

Book with confidence

Springfield to Chicago Flights

The cheapest times to fly from Springfield 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 Springfield to Chicago are during the month of November. You can find some of the cheapest flights from Springfield to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Springfield to Chicago

Sunday is one of the best days to book for cheap flights from Springfield 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 Springfield 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 Springfield to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $139 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 Springfield 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 Springfield 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.

 

Springfield to Chicago Flights

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*Available to One Key members.