$49 Cheap Flights from St. Louis (STL) to Chicago (MDW)

View $49 flight on Mon, Oct 13, 2025Opens in a new window

Popular airlines from St. Louis Lambert Intl. Airport (STL) to Chicago Midway Airport (MDW)

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Cheap Flights from St. Louis to Chicago (STL-MDW)

Prices were available within the past 7 days and start at $49 for one-way flights and $97 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Nov 13 - Sat, Nov 15
STL
St. Louis
MDW
Chicago
$97 Roundtrip, just found
$97
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Nov 13 from St. Louis to Chicago, returning Sat, Nov 15, priced at $97 just found
Southwest Airlines
Thu, Nov 13 - Sat, Nov 15
STL
St. Louis
MDW
Chicago
$107 Roundtrip, just found
$107
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Nov 13 from St. Louis to Chicago, returning Sat, Nov 15, priced at $107 just found
Southwest Airlines
Thu, Nov 13 - Sat, Nov 15
STL
St. Louis
MDW
Chicago
$112 Roundtrip, just found
$112
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Nov 13 from St. Louis to Chicago, returning Sat, Nov 15, priced at $112 just found
Southwest Airlines
Thu, Nov 13 - Sat, Nov 15
STL
St. Louis
MDW
Chicago
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Nov 13 from St. Louis to Chicago, returning Sat, Nov 15, priced at $117 just found
Southwest Airlines
Thu, Nov 13 - Sat, Nov 15
STL
St. Louis
MDW
Chicago
$122 Roundtrip, just found
$122
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Nov 13 from St. Louis to Chicago, returning Sat, Nov 15, priced at $122 just found
Frontier Airlines
Fri, Oct 31 - Mon, Nov 3
STL
St. Louis
MDW
Chicago
$126 Roundtrip, found 11 hours ago
$126
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Fri, Oct 31 from St. Louis to Chicago, returning Mon, Nov 3, priced at $126 found 11 hours ago
Southwest Airlines
Thu, Oct 30 - Sat, Nov 1
STL
St. Louis
MDW
Chicago
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Oct 30 from St. Louis to Chicago, returning Sat, Nov 1, priced at $127 found 2 days ago
Southwest Airlines
Thu, Nov 13 - Fri, Nov 14
STL
St. Louis
MDW
Chicago
$130 Roundtrip, found 4 days ago
$130
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Nov 13 from St. Louis to Chicago, returning Fri, Nov 14, priced at $130 found 4 days ago
Frontier Airlines
Thu, Nov 6 - Sat, Nov 8
STL
St. Louis
MDW
Chicago
$132 Roundtrip, found 12 hours ago
$132
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Thu, Nov 6 from St. Louis to Chicago, returning Sat, Nov 8, priced at $132 found 12 hours ago
Delta
Wed, Nov 12 - Mon, Nov 17
STL
St. Louis
MDW
Chicago
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Nov 12 from St. Louis to Chicago, returning Mon, Nov 17, priced at $139 found 2 days ago

Find the cheapest month to fly from St. Louis (STL) to Chicago (MDW)

September is typically the cheapest month to fly

From $77 - $524 per traveler.

Frequently asked questions

How much does a flight from Lambert-St. Louis Intl. Airport (STL) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $49 or cheap return flight from $97 from Lambert-St. Louis Intl. Airport (STL) 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 Lambert-St. Louis Intl. Airport (STL) to Midway Intl. Airport (MDW)?
The cheapest month to fly from STL to MDW is November, when there's less demand. Off-peak months are often when airlines offer lower prices between these airports.
Which airlines fly direct from Lambert-St. Louis Intl. Airport (STL) to Midway Intl. Airport (MDW)?
Jump on a direct flight with Southwest Airlines and head straight from Lambert-St. Louis Intl. Airport (STL) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from Lambert-St. Louis Intl. Airport (STL) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll fly you from STL to MDW. Then, sort your results by "Price (lowest to highest)" to score the best deal available.
How many flights per day from Lambert-St. Louis Intl. Airport (STL) to Midway Intl. Airport (MDW)?
When jetting out of Lambert-St. Louis Intl. Airport (STL), you can pick from an average of 3 daily nonstop flights to Midway Intl. Airport (MDW).
What are the most popular departure times for flights from Lambert-St. Louis Intl. Airport (STL) to Midway Intl. Airport (MDW)?
The 2 PM departures from STL to MDW are typically the busiest. They can also be more expensive. If you want to save money, choose a less crowded time to fly.
What day of the week has the most flights from STL to MDW?
Fly on a Friday if you're searching for the biggest selection of flights from Lambert-St. Louis Intl. Airport (STL) to Midway Intl. Airport (MDW).
What is the earliest flight from Lambert-St. Louis Intl. Airport (STL) to Midway Intl. Airport (MDW)?
Take the earliest flight at around 6:25AM UTC-6, heading out of Lambert-St. Louis Intl. Airport (STL). You'll be flying for about 1h 15m, landing at Midway Intl. Airport (MDW) at approximately 7:40AM UTC-6.
How long does it take to fly from Lambert-St. Louis Intl. Airport (STL) to Midway Intl. Airport (MDW)?
Flights from STL to MDW have an average travel time of 1 hour and 10 minutes. The total distance between these two airports is 250 mi.
What is the best time to fly from Lambert-St. Louis Intl. Airport (STL) to Midway Intl. Airport (MDW)?
To arrive at Midway Intl. Airport (MDW) on schedule, opt for a flight that takes off from Lambert-St. Louis Intl. Airport (STL) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 Lambert-St. Louis Intl. Airport (STL)?
Board a direct flight from Lambert-St. Louis Intl. Airport (STL) to Chicago and land at O'Hare Intl. Airport (ORD). Another convenient gateway to this city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Lambert-St. Louis Intl. Airport (STL) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from STL to MDW right before your getaway is usually more expensive. But if you're flexible with your departure dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a STL to MDW flight and hotel package?
You'll typically save money by booking a STL 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 everything in one place. After choosing your ideal flights and accommodations, consider other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from Lambert-St. Louis Intl. Airport (STL) to Midway Intl. Airport (MDW)?
In most instances, you can reschedule or cancel your STL to MDW flight. However, there may be additional fees, especially if you made your booking over 24 hours ago. Check your itinerary for the airline's fees and guidelines on flight changes, or if you want more details, head to our Customer Service portal.

Travel information

Travel information

Origin airport
Lambert-St. Louis Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$97
Distance
251 mi
Average flight time
1 hour 8 mins

Book with confidence

Book with confidence

St. Louis to Chicago Flights

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

 

The best time to book a flight from St. Louis to Chicago

Sunday is one of the best days to book for cheap flights from St. Louis 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 St. Louis 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 St. Louis to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $49 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 St. Louis 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 St. Louis 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.

 

St. Louis to Chicago Flights

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