$64 Cheap Flights from St Louis to Chicago Midway

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      Travellers and cabin class, 1 Adult, Economy
      Southwest Airlines

      Compare St Louis to Chicago Midway flight deals

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

      Book the best Chicago Midway fare with no extra fees

      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 $149. Find the lowest prices on one-way and return tickets right here.

      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 October.

      Direct flights from St Louis to Chicago Midway

      Southwest Airlines

      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$64
      Cheapest month to flyOctober
      Average flight time1 hr, 7 mins
      Most popular airlineSouthwest Airlines
      Average flights per week41

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

      The best price we found for a return flight from St Louis to Chicago Midway is $148. 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.
      1 hour and 7 minutes is the average flight time from St Louis to Chicago Midway.
      Southwest Airlines flies direct from St Louis to Chicago Midway.
      As of August 2026, there are 41 flights per week flying from St Louis to Chicago Midway.
      The cheapest month to fly from St Louis to Chicago Midway is usually September.
      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 Thursday, 10 September 2026.
      Yes – the average flight time is 1 hour and 7 minutes.
      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.

      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.

      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)

      • $64 is the best price for a one-way St Louis Airport to Chicago Midway Airport flight. Return flights start from $149. 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)

      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.

      Getting from Chicago Midway Airport (MDW) to central Chicago

      • MDW is located at 5700 South Cicero.

      • Chicago Midway Airport to the centre of Chicago has a drive time of around 25 minutes. It's approximately 16 kilometres away.

      • If you're travelling by public transport, expect a journey of around 30 minutes.

      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 (61ºF) and 28ºC (82ºF).

      • If you want to travel in cooler conditions, look for a cheap ticket from STL to MDW in January. Average temperatures are between -12ºC (10ºF) and 3ºC (37ºF) 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.

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.