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Uncover the best deals on St Louis to Chicago flights by comparing fares from hundreds of airlines and agencies.
Good to Know: Cheapest and Fastest STL - MDW Flights
Useful information for finding best airline tickets from Lambert St Louis International to Chicago Midway International on your next trip.
Cheapest Round Trip Flight
$589
Southwest Airlines
• 1 stop
• 5h 50m
Oct 08 – Oct 15
The cheapest round trip flight from St Louis to Chicago (STL-MDW-STL) is currently $589
Cheapest Direct Flight
$298
United Airlines
• nonstop
• 2h 11m
Oct 08
The cheapest nonstop flight from St Louis to Chicago (STL-MDW) is currently $298
Fastest Flight
1h 45m
The fastest nonstop flight from St Louis to Chicago (STL-MDW) takes 1h 45m
Top Airlines Flying from St Louis to Chicago
Latest Flight Deals from St Louis (STL) to Chicago (MDW)
Compare and book low fare round-trip air tickets from St Louis to Chicago. Ideal for travelers with confirmed return itineraries.
Oct 08 - Oct 15, Economy
St Louis → Chicago
5h 50m
10:20 AM - 2:10 PM • 1 stop
St Louis → Chicago
1h 55m
10:05 PM - 11:20 PM • nonstop
Southwest Airlines
Oct 08 - Oct 15, Economy
St Louis → Chicago
1h 50m
10:50 AM - 12:00 PM • nonstop
St Louis → Chicago
7h 20m
4:15 PM - 8:55 PM • 1 stop
Southwest Airlines
Oct 08 - Oct 15, Economy
St Louis → Chicago
12h 5m
5:50 PM - 1:15 AM • 1 stop
St Louis → Chicago
5h 5m
11:50 AM - 2:55 PM • 1 stop
Southwest Airlines
Oct 08 - Oct 15, Economy
St Louis → Chicago
10h 55m
1:00 PM - 7:55 PM • 1 stop
St Louis → Chicago
5h 5m
11:50 AM - 2:55 PM • 1 stop
Southwest Airlines
Oct 08 - Oct 15, Economy
St Louis → Chicago
10h 5m
5:50 PM - 11:55 PM • 1 stop
St Louis → Chicago
7h 20m
4:15 PM - 8:55 PM • 1 stop
Southwest Airlines
Flying to Chicago soon? We've surfaced some of the most affordable last-minute flights from St Louis to Chicago, ideal for urgent plans or spontaneous trips.
Oct 08 - Oct 15, Economy
St Louis → Chicago
5h 50m
10:20 AM - 2:10 PM • 1 stop
St Louis → Chicago
1h 55m
10:05 PM - 11:20 PM • nonstop
Southwest Airlines
Oct 08 - Oct 15, Economy
St Louis → Chicago
1h 50m
10:50 AM - 12:00 PM • nonstop
St Louis → Chicago
7h 20m
4:15 PM - 8:55 PM • 1 stop
Southwest Airlines
Oct 08 - Oct 15, Economy
St Louis → Chicago
12h 5m
5:50 PM - 1:15 AM • 1 stop
St Louis → Chicago
5h 5m
11:50 AM - 2:55 PM • 1 stop
Southwest Airlines
Oct 08 - Oct 15, Economy
St Louis → Chicago
10h 55m
1:00 PM - 7:55 PM • 1 stop
St Louis → Chicago
5h 5m
11:50 AM - 2:55 PM • 1 stop
Southwest Airlines
Oct 08 - Oct 15, Economy
St Louis → Chicago
10h 5m
5:50 PM - 11:55 PM • 1 stop
St Louis → Chicago
7h 20m
4:15 PM - 8:55 PM • 1 stop
Southwest Airlines
Looking for the fastest way to Chicago? These direct flight options from STL to MDW offer both convenience and value—no layovers, just straight to your destination.
Oct 08 - Oct 15, Economy
St Louis → Chicago
2h 11m
8:00 AM - 9:31 AM • nonstop
St Louis → Chicago
2h 9m
9:30 PM - 10:59 PM • nonstop
United Airlines
Oct 08 - Oct 15, Economy
St Louis → Chicago
1h 45m
2:00 PM - 3:05 PM • nonstop
St Louis → Chicago
1h 50m
2:45 PM - 3:55 PM • nonstop
Southwest Airlines
Oct 08 - Oct 15, Economy
St Louis → Chicago
1h 45m
6:10 PM - 7:15 PM • nonstop
St Louis → Chicago
1h 50m
2:45 PM - 3:55 PM • nonstop
Southwest Airlines
Oct 08 - Oct 15, Economy
St Louis → Chicago
1h 45m
5:25 AM - 6:30 AM • nonstop
St Louis → Chicago
1h 50m
5:50 PM - 7:00 PM • nonstop
Southwest Airlines
Oct 08 - Oct 15, Economy
St Louis → Chicago
1h 50m
10:50 AM - 12:00 PM • nonstop
St Louis → Chicago
1h 50m
7:50 AM - 9:00 AM • nonstop
Southwest Airlines
FAQs on St Louis to Chicago Flights
What are the airports in St Louis?
STL
What’s the most popular airline flying from STL to MDW?
The most popular airline flying from St Louis to Chicago are
Can I fly from STL to MDW non-stop?
Yes, you can fly STL to MDW non-stop on
Which airlines fly nonstop between St Louis and Chicago?
The non-stop flights between St Louis and Chicago are .
What’s the earliest departure time from STL to MDW Airport?
The earliest flight leaves STL at 5:25 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my St Louis to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from STL to MDW?
Read the fare rules of the St Louis to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from St Louis and Chicago?
operate flights between St Louis and Chicago
How long does a flight from St Louis to Chicago take?
It takes approximately 1 hour to fly non-stop from STL to MDW, which is 251.08 miles by air.
Which airlines provide the cheapest flights from St Louis (STL) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from STL were found on WN : USD 598
Do I need a passport to fly between STL and MDW?
No
What’s the latest departure time from STL to MDW ?
The last flight leaves STL at 10:00 pm
St Louis (STL) to Chicago (MDW): Airport Information
| Origin Airport | Lambert St Louis International , St Louis, US |
| Destination Airport | Chicago Midway International , Chicago, US |
| Distance | 251 miles |
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