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Cheap Flights from St Louis (STL) to Chicago Midway (MDW)

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  4. 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

Book the best Chicago Midway fare with no extra fees

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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 to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.£57 per passenger.Departing Thu, 21 Aug, returning Thu, 28 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Thu, 21 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 28 Aug, arriving in St Louis.Price includes taxes and charges.From £57, select.
Thu, 21 AugSTL - MDW with Southwest Airlines
Direct
Thu, 28 AugMDW - STL with Southwest Airlines
Direct
from £57
Chicago.£57 per passenger.Departing Tue, 9 Sep, returning Tue, 16 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Tue, 9 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 16 Sep, arriving in St Louis.Price includes taxes and charges.From £57, select.
Tue, 9 SepSTL - MDW with Southwest Airlines
Direct
Tue, 16 SepMDW - STL with Southwest Airlines
Direct
from £57
Chicago.£84 per passenger.Departing Sat, 30 Aug, returning Tue, 2 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Sat, 30 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 2 Sep, arriving in St Louis.Price includes taxes and charges.From £84, select.
Sat, 30 AugSTL - MDW with Southwest Airlines
Direct
Tue, 2 SepMDW - STL with Southwest Airlines
Direct
from £84
Chicago.£133 per passenger.Departing Sun, 29 Jun, returning Thu, 3 Jul.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from St Louis on Sun, 29 Jun, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 3 Jul, arriving in St Louis.Price includes taxes and charges.From £133, select.
Sun, 29 JunSTL - MDW with Frontier Airlines
1 stop
Thu, 3 JulMDW - STL with Frontier Airlines
1 stop
from £133
Chicago.£161 per passenger.Departing Fri, 20 Jun, returning Fri, 27 Jun.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from St Louis on Fri, 20 Jun, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 27 Jun, arriving in St Louis.Price includes taxes and charges.From £161, select.
Fri, 20 JunSTL - MDW with Frontier Airlines
1 stop
Fri, 27 JunMDW - STL with Frontier Airlines
1 stop
from £161
Chicago.£166 per passenger.Departing Fri, 7 Nov, returning Fri, 14 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Fri, 7 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 14 Nov, arriving in St Louis.Price includes taxes and charges.From £166, select.
Fri, 7 NovSTL - MDW with Southwest Airlines
Direct
Fri, 14 NovMDW - STL with Southwest Airlines
Direct
from £166
Chicago.£168 per passenger.Departing Mon, 28 Jul, returning Mon, 4 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Mon, 28 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 4 Aug, arriving in St Louis.Price includes taxes and charges.From £168, select.
Mon, 28 JulSTL - MDW with Southwest Airlines
Direct
Mon, 4 AugMDW - STL with Southwest Airlines
Direct
from £168
Chicago.£168 per passenger.Departing Wed, 23 Jul, returning Wed, 30 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from St Louis on Wed, 23 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 30 Jul, arriving in St Louis.Price includes taxes and charges.From £168, select.
Wed, 23 JulSTL - MDW with Southwest Airlines
Direct
Wed, 30 JulMDW - STL with Southwest Airlines
Direct
from £168
How did we find these deals? The deals you see here are the lowest prices for flight tickets from St Louis to Chicago Midway found in the last 4 days, and are subject to change and availability.

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.
Jun
from £161
Jul
from £168
Aug
from £57
Sep
from £57
Oct
from £209
Nov
from £166
Dec
Find prices
Jan
Find prices
Feb
from £332
Mar
Find prices
Apr
Find prices
May
Find prices

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£57
Cheapest month to flySeptember
Average flight time1 hr, 9 mins
Most popular airlineSouthwest Airlines
Average flights per week38

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 £57. 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 9 minutes is the average flight time from St Louis to Chicago Midway.
Southwest Airlines flies direct from St Louis to Chicago Midway.
As of June 2025, there are 38 flights per week flying from St Louis to Chicago Midway.
The cheapest month to fly from St Louis to Chicago Midway is usually June 2025.
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 Tuesday, 9 September 2025.
Yes – the average flight time is 1 hour and 9 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 Lambert-St. Louis International Airport (STL) to Chicago Midway International Airport (MDW): what you need to know

  • The average time for a direct flight from Lambert-St. Louis International Airport to Chicago Midway International Airport is 1 hour 10 minutes.

  • St Louis and Chicago are both in the UTC-5 timezone. This means there's no time difference to adjust for.

  • Every week, there are 27 Lambert-St. Louis International Airport to Chicago Midway International Airport flights. If you prefer to take off as soon as possible, select the 05:25 Southwest Airlines flight. If you'd rather make the most of your time before you fly, the last flight is at 22:55 with Southwest Airlines.

  • For a smooth journey, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This ensures you have enough time to board your STL to MDW flight.

  • You'll likely experience longer lines during popular months such as July. Arriving up to four hours ahead of an international flight and two hours for a domestic departure is a wise move.

  • Southwest Airlines offers direct flights from Lambert-St. Louis International Airport to Chicago Midway International Airport. Book with this popular airline, then get ready to tick off the sights in Chicago — and maybe even more of United States if you have time.

  • Southwest Airlines is the most frequently booked airline on this route.

  • With an impressive 84.86% of services arriving as scheduled, Southwest Airlines is the most punctual carrier operating STL to MDW flights.

  • If you want to break up your flight, just uncheck 'Direct flights only' when searching for your ticket from Lambert-St. Louis International Airport to Chicago Midway International Airport. Here are the top stopovers between STL and MDW:

    • Kansas City International Airport

    • Detroit Metropolitan Wayne County Airport

    • Nashville International Airport

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

  • The lowest price we've found for a one-way Lambert-St. Louis International Airport to Chicago Midway International Airport flight is £28. A return fare is currently £57. Depending on the availability when you book, these fares may change.

  • To score cheap tickets from STL to MDW, book your journey six months before your departure.

  • The cheapest month for flights from Lambert-St. Louis International Airport to Chicago Midway International Airport is May. Use the 'Whole month' tool to find the lowest prices if you have flexible dates.

  • You won't have to check every day to find out if fares have dropped when you create a Price Alert. We'll send you an update as soon as there's a new deal on cheap flights from STL to MDW.

  • Tailor your trip using filters. Select your preferred arrival and departure times, airlines and total journey duration. You can also sort your results by 'Fastest,' 'Best' or 'Cheapest' flights from Lambert-St. Louis International Airport to Chicago Midway International Airport.

Handy information about Lambert-St. Louis International Airport (STL)

  • STL's address is 10701 Lambert International Blvd..

  • When it comes to the on-time performance of Lambert-St. Louis International Airport, 78.04% of flights meet their scheduled arrival time.

  • Central St Louis to Lambert-St. Louis International Airport is approximately 16 miles. Depending on traffic, it'll take about 20 minutes to get there if you're driving, catching a cab or ride-sharing.

  • You can expect a journey time of around 35 minutes on public transport.

  • Searching for a handy hotel close to STL? If you've booked an early flight from Lambert-St. Louis International Airport to Chicago Midway International Airport, these stays will have you moments from your departure lounge:

    • La Quinta Inn by Wyndham St. Louis Hazelwood - Airport North

    • Extended Stay America Select Suites - St Louis - Airport - Central

    • Best Western St. Louis Airport North Hotel Suites

Arriving at Chicago Midway International Airport (MDW)

  • The last thing you want is a long trip to your hotel if you're getting in late on a Lambert-St. Louis International Airport to Chicago Midway International Airport flight. Check in to one of these accommodation options near MDW instead:

    • Holiday Inn Chicago – Midway Airport S

    • Carlton Inn Midway

    • Skylark Motel

  • Explore without limits with a Chicago Midway International Airport rental car. Pick up your wheels from Dollar, Hertz or Budget and venture far and wide through Chicago and beyond.

  • Booking your vehicle from Chicago Midway International Airport about four weeks in advance can help you secure the lowest rate.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • You'll find MDW at 5700 South Cicero.

  • Chicago Midway International Airport to the centre of Chicago has a drive time of about 20 minutes. It's approximately 12 miles away.

  • Getting to the centre by public transport takes roughly 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • July is the busiest month for flights from Lambert-St. Louis International Airport to Chicago Midway International Airport. For smaller crowds, go to Chicago in May.

  • Lock in your flight from Lambert-St. Louis International Airport to Chicago Midway International Airport for July if you want to visit Chicago during its warmest month. Expect temperatures of between 15ºC (59ºF) and 29ºC (84ºF).

  • Look for cheap tickets from STL to MDW in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be discovered after you've seen Chicago. Around 280 miles away to the south-east, well-known attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another essential stop in United States and is around 160 miles south-east of Chicago. No trip is complete without dropping by The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from St Louis to Chicago

  • Car hire from Chicago Midway
  • Hotels in Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.

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