STL - MDW

$31 Find Cheap Flights from St. Louis to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from St. Louis to Midway departing on 8/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from St. Louis to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from St. Louis to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Expert advice
Useful Info
Flights Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from St. Louis to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from St. Louis to Midway

Wed, Aug 6 - Wed, Aug 13
Southwest Logo
2:05 pm - 3:10 pmSTL-MDW
1h 05mnonstop
Southwest Logo
8:25 pm - 9:40 pmMDW-STL
1h 15mnonstop
$61Southwest
Find Deal
Wed, Aug 6 - Wed, Aug 13
Southwest Logo
7:10 am - 8:20 amSTL-MDW
1h 10mnonstop
Southwest Logo
7:05 am - 12:35 pmMDW-STL
5h 30m1 stop
$71Southwest
Find Deal
Sat, Aug 16 - Mon, Aug 18
Southwest Logo
6:00 pm - 7:05 pmSTL-MDW
1h 05mnonstop
Southwest Logo
6:05 pm - 7:20 pmMDW-STL
1h 15mnonstop
$76Southwest
Find Deal
Sat, Aug 16 - Sat, Aug 16
Southwest Logo
5:45 am - 11:25 amSTL-MDW
5h 40m1 stop
Southwest Logo
1:20 pm - 5:00 pmMDW-STL
3h 40m1 stop
$81Southwest
Find Deal
Sat, Nov 8 - Tue, Nov 11
Delta Logo
3:30 pm - 9:44 pmSTL-MDW
6h 14m1 stop
Delta Logo
6:00 am - 10:40 amMDW-STL
4h 40m1 stop
$177Delta
Find Deal
Wed, Aug 6 - Wed, Aug 13
Delta Logo
6:30 am - 12:29 pmSTL-MDW
5h 59m2 stops
Delta Logo
6:04 am - 12:31 pmMDW-STL
6h 27m1 stop
$182Delta
Find Deal
Fri, Aug 22 - Fri, Aug 22
Delta Logo
6:40 am - 12:28 pmSTL-MDW
5h 48m1 stop
Delta Logo
6:42 pm - 11:14 pmMDW-STL
4h 32m1 stop
$207Delta
Find Deal
Thu, Aug 7 - Thu, Aug 14
Frontier Logo
2:36 pm - 11:17 pmSTL-MDW
8h 41m1 stop
Frontier Logo
6:20 am - 1:34 pmMDW-STL
7h 14m1 stop
$224Frontier
Find Deal
Fri, Aug 29 - Mon, Sep 1
Frontier Logo
2:01 pm - 11:27 pmSTL-MDW
9h 26m1 stop
Frontier Logo
6:15 am - 12:56 pmMDW-STL
6h 41m1 stop
$229Frontier
Find Deal
Thu, Jul 31 - Sun, Aug 3
Frontier Logo
2:36 pm - 11:17 pmSTL-MDW
8h 41m1 stop
Frontier Logo
7:40 am - 6:59 pmMDW-STL
11h 19m1 stop
$256Frontier
Find Deal
Expert advice

Expert advice for your flight from St. Louis to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
STL

Avoid peak travel times at STL to minimize wait times. Early mornings and afternoons are busiest, especially in Terminal 2.

Read more about STLby Yulia Denisyuk
MDW

Take the CTA Orange Line from MDW to downtown Chicago for a quick 25-30 minute ride, avoiding traffic delays.

Read more about MDWby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Yulia Denisyuk

Yulia Denisyuk

Expert on STL

Yulia Denisyuk

Yulia Denisyuk

Yulia is a freelance journalist who’s dispatched from 90+ countries. Her work focuses on cultures, adventure trips and air travel, appearing in NatGeo, NYT, CNTraveler, and more. For past assignments, she’s stayed with nomads in Mongolia and learned the art of Imigongo in Rwanda. She’s based in Chicago; in winter she often questions that decision.

Read more
Useful Info

KAYAK's insights & trends for St. Louis to Midway flights

Get data-powered insights and trends into flights from St. Louis to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from St. Louis to Chicago Midway Airport?

The average price of all round-trip flights from St. Louis to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

For St. Louis to Chicago Midway Airport, Wednesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago Midway Airport back to St. Louis, the best deals are generally found on Wednesday, with Monday being the most expensive.

What is the cheapest month to fly from St. Louis to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from St. Louis to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from St. Louis to Chicago Midway Airport is December, where tickets cost $243 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is $422 and $379 respectively.

Can I save money by flying with a layover from St. Louis to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $259 on average.

Find deals

Good to know

Low seasonJanuary
High seasonNovember
Cheapest flight$31
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from St. Louis to Chicago Midway Airport

When to book flights from St. Louis to Midway

Are your dates flexible? Find out the best times to travel from St. Louis to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking St. Louis to Chicago Midway Airport flights

  • What is the cheapest flight from St. Louis to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from St. Louis to Chicago Midway Airport was $31 for a one-way ticket and $61 for a round-trip.

  • Do I need a passport to fly between St. Louis and Chicago Midway Airport?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from St. Louis to Chicago Midway Airport?

    When flying out of St. Louis you will be using Lambert-St Louis. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from St. Louis to Chicago Midway Airport?

    American Airlines, Delta, and Alaska Airlines offer inflight Wi-Fi service on the St. Louis to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from St. Louis to Chicago Midway Airport?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the St. Louis to Chicago Midway Airport flight route.

  • On which days can I fly direct from St. Louis to Chicago Midway Airport?

    There are nonstop flights from St. Louis to Chicago Midway Airport on a daily basis.

  • How does KAYAK find such low prices on flights from St. Louis to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from St. Louis to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from St. Louis to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from St. Louis is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from St. Louis to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to St. Louis with another airline. Booking your flights between St. Louis and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from St. Louis to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from St. Louis up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from St. Louis to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $159 or less one-way and $271 or less round-trip.

Prefer to fly direct from St. Louis to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Lambert-St Louis to Chicago Midway.
Find which airlines fly direct from Lambert-St Louis Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Lambert-St Louis to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Lambert-St Louis

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from St. Louis to Midway

 
See real verified KAYAK customer reviews for airlines flying from St. Louis to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from St. Louis to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4252 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.6Entertainment
7.0Food
Airline reviews

It was one and half hour late... Not sure if any other experience matters.

4.0 OkaySudhir, Jul 2025LGA - MCI
Read more Southwest reviews

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Everything you need to know for your flight from St. Louis to Midway

Information on your arrival and departure airports

St. Louis (STL)
Midway (MDW)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.