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Midway

$59+ Cheap flights from St. Louis (STL) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
STL — MDW
Jun 11 — Jun 181
Thu 6/11
Thu 6/18
1 adult, Economy
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Cheap flight deals from St. Louis to Midway

Cheapest flights from St. Louis to Midway
Explore the most affordable flight options available from St. Louis to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 12, 2026.

This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:30 pm
STL
-
MDW
Nonstop1h 05m
Southwest
Mon 6/89:35 pm
MDW
-
STL
Nonstop1h 15m
Southwest
Deal found 5/11$191
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:10 pm
STL
-
MDW
1 stop4h 23m
Delta
Thu 8/139:24 am
MDW
-
STL
1 stop3h 50m
Delta
Deal found 5/8$194
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/284:00 pm
STL
-
MDW
1 stop6h 20m
Southwest
Mon 6/19:30 pm
MDW
-
STL
Nonstop1h 15m
Southwest
Deal found 5/7$201
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/286:31 pm
STL
-
MDW
1 stop16h 38m
Frontier
Thu 7/1612:11 pm
MDW
-
STL
1 stop20h 46m
Frontier
Deal found 5/10$213
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:30 am
STL
-
MDW
1 stop6h 16m
Delta
Sat 6/271:26 pm
MDW
-
STL
1 stop3h 57m
Delta
Deal found 5/11$218
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:45 am
STL
-
MDW
1 stop5h 57m
Delta
Sat 5/307:13 pm
MDW
-
STL
1 stop4h 08m
Delta
Deal found 5/8$221
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:40 am
STL
-
MDW
Nonstop1h 10m
Southwest
Sat 5/309:15 am
MDW
-
STL
Nonstop1h 15m
Southwest
Deal found 5/8$226
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/105:55 pm
STL
-
MDW
Nonstop1h 10m
Southwest
Fri 6/121:00 pm
MDW
-
STL
Nonstop1h 10m
Southwest
Deal found 5/8$227
This Expedia deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/265:06 pm
STL
-
MDW
1 stop5h 05m
Frontier
Sun 6/286:00 am
MDW
-
STL
1 stop11h 30m
Frontier
Deal found 5/11$230
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/86:30 am
STL
-
MDW
1 stop6h 16m
Delta
Tue 6/99:17 am
MDW
-
STL
2 stops7h 29m
Delta
Deal found 5/7$233

Find flight deals from St. Louis to Midway

Discover tips and strategies to find the most affordable flight options for your journey from St. Louis (STL) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$191
(Southwest)

One-way from

$59
(Southwest)

Popular in

July

Cheapest in

November

Average price

$367

Good round-trip deal

$337 or less

Good one-way deal

$219 or less
Provider with most accurate pricing for Lambert-St Louis-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Lambert-St Louis-Chicago Midway flights.
Search Deals
From Lambert-St Louis to Chicago Midway
Search Deals
One-way flight from Lambert-St Louis to Chicago Midway
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Lambert-St Louis to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Lambert-St Louis to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from St. Louis to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 12, 2026.
Use the filters below to find and compare flights from St. Louis to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 5/28

9:40 pm-10:45 pm

Nonstop1h 05m

Chicago Midway

Mon 6/1

7:50 am-9:05 am

Nonstop1h 15m

$191

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 8/20

5:40 pm-10:20 pm

1 stop4h 40m

Chicago Midway

Thu 8/27

5:55 am-10:10 am

1 stop4h 15m

$211

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 6/24

6:30 am-12:46 pm

1 stop6h 16m

Chicago Midway

Sat 6/27

1:26 pm-10:04 pm

2 stops8h 38m

$223

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 6/10

9:30 pm-10:35 pm

Nonstop1h 05m

Chicago Midway

Mon 6/15

7:50 am-9:10 am

Nonstop1h 20m

$227

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 7/15

5:40 am-6:45 am

Nonstop1h 05m

Chicago Midway

Sat 7/18

8:30 pm-9:45 pm

Nonstop1h 15m

$237

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 6/24

5:55 pm-7:05 pm

Nonstop1h 10m

Chicago Midway

Sat 6/27

5:05 pm-11:45 pm

2 stops6h 40m

$242

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Tue 7/14

6:30 am-12:38 pm

1 stop6h 08m

Chicago Midway

Sat 7/18

1:18 pm-5:19 pm

1 stop4h 01m

$257
Quickest round-trip

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 8/13

2:20 pm-3:25 pm

Nonstop1h 05m

Chicago Midway

Sun 8/16

8:25 pm-9:35 pm

Nonstop1h 10m

$264

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 6/6

8:50 pm-9:55 pm

Nonstop1h 05m

Chicago Midway

Sat 6/13

6:30 am-11:25 am

1 stop4h 55m

$274

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 6/25

6:30 am-12:46 pm

1 stop6h 16m

Chicago Midway

Fri 6/26

5:11 pm-11:56 pm

1 stop6h 45m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from St. Louis to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from St. Louis to Midway in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on St. Louis-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on St. Louis-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from St. Louis-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on St. Louis-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for St. Louis-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from St. Louis to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from St. Louis with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from St. Louis to Chicago Midway Airport

What is the cheapest time of day to fly from STL to MDW?

Find hourly flight availability from St. Louis to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 12, 2026.

When flying from St. Louis to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 17% versus a flight in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from St. Louis to Midway. Price data was last updated on May 9, 2026.

Travelers seeking maximum savings on their St. Louis to Chicago Midway Airport flight should consider departing on Sunday evenings when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from St. Louis to Chicago Midway Airport?

The best insider tips for St. Louis to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your St. Louis to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Taryn White

Taryn White

Expert on STL

Taryn White is a freelance travel writer, digital creator, and travel advisor who has visited nearly 100 countries and all 50 states. She’s familiar with many airports and enjoys beach hopping, boutique hotels, spa experiences, and exploring local culture. Her work has appeared in Travel + Leisure, Condé Nast Traveler, National Geographic, Smithsonian Magazine, AFAR, and more.

Read more

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated May 12, 2026.
Read through reviews of airlines operating flights from St. Louis to Chicago Midway Airport, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,295 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from St. Louis to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from St. Louis to Chicago Midway?

    Located just 12.7 mi from the city center, Lambert-St Louis is the airport most travelers will use when flying to Chicago Midway from St. Louis. Booking flights from Lambert-St Louis (STL) to Chicago Midway should be relatively easy as there are 3 daily outbound flights to Chicago Midway from 1 airline.

  • How long is the flight from St. Louis to Chicago Midway Airport?

    A quick flight from St. Louis to Chicago Midway Airport can take about 1h 05m. Southwest provides one of the quickest options available for as low as $191. Airlines will cover a distance of 251 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from St. Louis to Chicago Midway Airport round-trip?

    Currently priced at $117, Southwest will fly you from St. Louis to Chicago Midway Airport and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Southwest is 71% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest flights from St. Louis to Chicago Midway Airport?

    The cheapest flight price from St. Louis to Chicago Midway Airport is $105. On average you can expect to pay $342. The most popular route, (Lambert-St Louis - Chicago Midway), can usually be booked for $117.

  • Can I find deals for flights from St. Louis to Midway that include hotel bookings?

    Yes. In addition to deals on St. Louis to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from St. Louis to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from St. Louis to Midway.

  • Can I find deals for business class flights from St. Louis to Midway?

    Yes. Cheapflights offers flight deals from St. Louis to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top airline flying from St. Louis to Midway

Discover the top airline that operate flights from St. Louis to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$117Average$457FlexibilityNo cancel feeOn-time63%

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