Cheap Flights from St Louis to Chicago Midway

Compare St Louis to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from St Louis to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from St Louis Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $200. Find the lowest prices on one-way and return tickets right here.

Chicago.$200 per passenger.Departing Tue, 25 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Tue, 25 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 1 Sep, arriving in St Louis.Price includes taxes and charges.From $200, select.

Chicago.$200 per passenger.Departing Sat, 15 Aug, returning Mon, 17 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Sat, 15 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 17 Aug, arriving in St Louis.Price includes taxes and charges.From $200, select.

Chicago.$200 per passenger.Departing Tue, 20 Oct, returning Tue, 20 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Tue, 20 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 20 Oct, arriving in St Louis.Price includes taxes and charges.From $200, select.

Chicago.$200 per passenger.Departing Sat, 5 Sep, returning Sun, 6 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Sat, 5 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 6 Sep, arriving in St Louis.Price includes taxes and charges.From $200, select.

Chicago.$284 per passenger.Departing Tue, 1 Dec, returning Tue, 15 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Tue, 1 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 15 Dec, arriving in St Louis.Price includes taxes and charges.From $284, select.

Chicago.$333 per passenger.Departing Tue, 22 Sep, returning Wed, 28 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Tue, 22 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 28 Oct, arriving in St Louis.Price includes taxes and charges.From $333, select.

Chicago.$333 per passenger.Departing Mon, 22 Feb, returning Sat, 27 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Mon, 22 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 27 Feb, arriving in St Louis.Price includes taxes and charges.From $333, select.

Chicago.$365 per passenger.Departing Tue, 3 Nov, returning Sat, 7 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Tue, 3 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 7 Nov, arriving in St Louis.Price includes taxes and charges.From $365, select.

Chicago.$388 per passenger.Departing Wed, 25 Nov, returning Wed, 2 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Wed, 25 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 2 Dec, arriving in St Louis.Price includes taxes and charges.From $388, select.

Chicago.$388 per passenger.Departing Fri, 30 Oct, returning Sun, 6 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Fri, 30 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 6 Dec, arriving in St Louis.Price includes taxes and charges.From $388, select.

Chicago.$407 per passenger.Departing Sun, 9 Aug, returning Thu, 15 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Sun, 9 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 15 Oct, arriving in St Louis.Price includes taxes and charges.From $407, select.

Chicago.$437 per passenger.Departing Fri, 31 Jul, returning Tue, 4 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from St Louis on Fri, 31 Jul, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 4 Aug, arriving in St Louis.Price includes taxes and charges.From $437, select.

Chicago.$515 per passenger.Departing Mon, 27 Jul, returning Thu, 30 Jul.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from St Louis on Mon, 27 Jul, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 30 Jul, arriving in St Louis.Price includes taxes and charges.From $515, select.

Chicago.$542 per passenger.Departing Fri, 31 Jul, returning Sat, 15 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Fri, 31 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 15 Aug, arriving in St Louis.Price includes taxes and charges.From $542, select.

Chicago.$593 per passenger.Departing Wed, 17 Feb, returning Sun, 7 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Wed, 17 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 7 Mar, arriving in St Louis.Price includes taxes and charges.From $593, select.

Chicago.$595 per passenger.Departing Tue, 29 Dec, returning Sat, 2 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Tue, 29 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 2 Jan, arriving in St Louis.Price includes taxes and charges.From $595, select.

Find the cheapest month to fly from St Louis to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like St Louis to Chicago Midway flights are currently cheapest in August.

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Direct flights from St Louis to Chicago Midway

St Louis to Chicago Midway: Alternative routes

Compare routes from St Louis to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

St Louis to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$200
Cheapest month to fly	August
Average flight time	1 hr, 7 mins
Most popular airline	Southwest Airlines
Average flights per week	40

Finding cheap flights from St Louis to Chicago Midway: Frequently asked questions

How much are return flights from St Louis to Chicago Midway?

The best price we found for a return flight from St Louis to Chicago Midway is $200. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from St Louis to Chicago Midway?

1 hour and 7 minutes is the average flight time from St Louis to Chicago Midway.

Which airlines fly direct from St Louis to Chicago Midway?

Southwest Airlines flies direct from St Louis to Chicago Midway.

How many flights are there a week from St Louis to Chicago Midway?

As of July 2026, there are 40 flights per week flying from St Louis to Chicago Midway.

When is the cheapest time to fly from St Louis to Chicago Midway?

The cheapest month to fly from St Louis to Chicago Midway is usually August.

Which upcoming date is cheapest to fly from St Louis Airport to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from St Louis Airport to Chicago Midway Airport on Saturday, 15 August 2026.

Can I get a direct flight from St Louis Airport to Chicago Midway Airport?

Yes – the average flight time is 1 hour and 7 minutes.

How can I find the best flight deal to Chicago Midway?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly from St Louis Airport to Chicago Midway with?

Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Travelling from St Louis Airport (STL) to Chicago Midway Airport (MDW): what you need to know

The average duration of a direct flight from St Louis Airport to Chicago Midway Airport is 1 hour 5 minutes.
Chicago's timezone is UTC-6, which is the same as St Louis.
Every week, there are 20 St Louis Airport to Chicago Midway Airport flights. To be on board as early as possible, opt for the 05:25 Southwest Airlines flight. If you'd rather make the most of your time before flying, the last flight is at 22:50 with Southwest Airlines.
Your STL to MDW flight won't wait if you're late, so don't forget to check in on time. Arrive up to one hour in advance for domestic flights and two hours ahead for international travel.
During popular months such as July, it's a good idea to get to the airport earlier. Plan to arrive two hours before domestic departures and four hours ahead of international flights when you travel during peak periods in general.
Southwest Airlines is your gateway to exploring Chicago (and maybe even some other great parts of the United States!). Check out the direct flights from St Louis Airport to Chicago Midway Airport offered by this airline.
Southwest Airlines has the highest passenger demand on this route.
With a reliable 82.54% of services arriving as planned, Southwest Airlines is the most punctual carrier operating STL to MDW flights.
Consider adding a stopover when booking your ticket from St Louis Airport to Chicago Midway Airport. Just uncheck 'Direct flights only' to break up your trip, or maybe even explore a new city along the way. Check out these options between STL and MDW:
- Detroit Wayne County Airport
- Nashville Airport
- Kansas City International Airport

How to find the cheapest flights from St Louis Airport (STL) to Chicago Midway Airport (MDW)

$100 is the best price for a one-way St Louis Airport to Chicago Midway Airport flight. Return flights start from $200. These fares can change based on demand and availability.
Don't leave everything to the last minute. You're more likely to find cheap tickets from STL to MDW if you book in advance. Airlines often offer some great early bird rates.
The cheapest month for flights from St Louis Airport to Chicago Midway Airport is May. Use the 'Whole month' tool to see the lowest airfares if you have a flexible travel schedule.
There's no need to check back in every day to find out if fares have gone down when you create a Price Alert. We'll update you as soon as there's a new deal on cheap flights from STL to MDW.
Pick your ideal arrival and departure times, number of stops and airlines with the filters. Or sort your results by 'Cheapest' to see the best deals on flights from St Louis Airport to Chicago Midway Airport.

Handy information about St Louis Airport (STL)

You'll find STL at 10701 Lambert International Blvd..
76% of flights that take off from St Louis Airport touch down at their destination on time.
St Louis Airport is about 24 kilometres from central St Louis. If you're driving, ride-sharing or catching a taxi from the centre, it'll take 25 minutes or so to get there, depending on the traffic.
Expect a journey time of roughly 30 minutes when using public transport.
Need a convenient hotel near STL? If you're boarding an early flight from St Louis Airport to Chicago Midway Airport, these accommodation options will have you moments from your departure lounge:

Arriving at Chicago Midway Airport (MDW)

If you're getting in on a late St Louis Airport to Chicago Midway Airport flight, nothing tops the convenience of being near the terminal. Grab your luggage from the carousel and then be showered and snoozing not long after at one of these hotels near MDW:
Pick up a Chicago Midway Airport rental car and discover Chicago and beyond with your own wheels. Dollar, Hertz and Budget are top outlets you can book with here.
Reserving your vehicle from Chicago Midway Airport about four weeks in advance gives you the best shot at securing a great deal.

When to fly to Chicago Midway Airport (MDW)

The quietest month for a flight from St Louis Airport to Chicago Midway Airport is December, while July is the busiest. Pick the ideal time to visit Chicago based on whether you prefer a faster pace or a more relaxed vibe.
Book your flight from St Louis Airport to Chicago Midway Airport for July if you want to go to Chicago during its warmest month. You can expect temperatures of between 16ºC and 28ºC.
If you want to travel in cooler conditions, look for a cheap ticket from STL to MDW in January. Average temperatures are between -12ºC and 3ºC then.

Explore more of the United States

You've visited Chicago, now it's time to explore other parts of the United States. Travel around 451 kilometres south-east to Columbus to check off its popular sights. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, there's plenty to keep you busy.
Indianapolis is another must-experience destination in the United States and is around 257 kilometres south-east of Chicago. No trip is complete without a visit to Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.