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Midway

$49+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
STL — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap 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 August 14, 2025.

Round-trip from

$87
(Southwest)

One-way from

$49
(Southwest)

Popular in

February

Cheapest in

December

Average price

$330

Good round-trip deal

$240 or less

Good one-way deal

$164 or less
From Lambert-St Louis to Chicago Midway
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One-way flight from Lambert-St Louis to Chicago Midway
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Highest demand for flights based on searches. 12% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Lambert-St Louis to Chicago Midway.
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Price to beat on a one-way flight from Lambert-St Louis to Chicago Midway.
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Find 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 August 14, 2025.

This Southwest deal was found by Cheapflights users on 8/14. 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 9/47:20 amSTL - MDW
Nonstop1h 10mSouthwest
Mon 9/85:25 amMDW - STL
1 stop5h 40mSouthwest
Deal found 8/14$87
This Southwest deal was found by Cheapflights users on 8/14. 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 9/137:15 amSTL - MDW
2 stops6h 15mSouthwest
Sat 9/203:55 pmMDW - STL
Nonstop1h 15mSouthwest
Deal found 8/14$92
This Southwest deal was found by Cheapflights users on 8/14. 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.
Sun 9/147:30 amSTL - MDW
Nonstop1h 10mSouthwest
Mon 9/1511:45 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 8/14$114
This Southwest deal was found by Cheapflights users on 8/13. 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 9/114:25 pmSTL - MDW
1 stop3h 25mSouthwest
Sun 9/146:45 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 8/13$124
This Southwest deal was found by Cheapflights users on 8/14. 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.
Fri 9/126:50 pmSTL - MDW
1 stop4h 00mSouthwest
Tue 9/164:30 pmMDW - STL
1 stop3h 35mSouthwest
Deal found 8/14$134
This Southwest deal was found by Cheapflights users on 8/14. 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.
Fri 9/54:20 pmSTL - MDW
Nonstop1h 10mSouthwest
Sun 9/77:25 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 8/14$151
This Southwest deal was found by Cheapflights users on 8/12. 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 9/177:10 amSTL - MDW
Nonstop1h 10mSouthwest
Sat 9/206:35 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 8/12$157

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 August 14, 2025.
Use the filters below to find and compare flights from St. Louis to Chicago Midway Airport that are best for you.

Fly from

St. Louis

Fly to

Midway

Route

Depart

Return

Price

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 9/4

1:50 pm-6:05 pm

1 stop4h 15m

Chicago Midway

Mon 9/8

2:35 pm-3:45 pm

Nonstop1h 10m

$87

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 9/13

11:55 am-6:35 pm

1 stop6h 40m

Chicago Midway

Mon 9/15

11:45 am-12:55 pm

Nonstop1h 10m

$87

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 9/13

11:35 am-4:35 pm

1 stop5h 00m

Chicago Midway

Sat 9/20

3:55 pm-5:10 pm

Nonstop1h 15m

$87

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Mon 9/15

4:20 pm-5:30 pm

Nonstop1h 10m

Chicago Midway

Wed 9/17

8:30 am-1:40 pm

1 stop5h 10m

$87

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 10/15

2:00 pm-7:25 pm

1 stop5h 25m

Chicago Midway

Thu 10/16

7:40 am-8:50 am

Nonstop1h 10m

$87

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Mon 9/8

7:20 pm-8:25 pm

Nonstop1h 05m

Chicago Midway

Wed 9/10

11:35 am-4:35 pm

1 stop5h 00m

$87

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Mon 9/8

4:15 pm-9:35 pm

1 stop5h 20m

Chicago Midway

Tue 9/9

5:40 pm-6:55 pm

Nonstop1h 15m

$87

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 9/17

8:50 pm-9:55 pm

Nonstop1h 05m

Chicago Midway

Sat 9/20

7:00 am-2:45 pm

1 stop7h 45m

$87

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Mon 10/27

5:00 am-9:55 am

1 stop4h 55m

$49

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Mon 11/10

3:50 pm-8:20 pm

1 stop4h 30m

$49

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 15 results
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The best insider tips for St. Louis to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-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.
Cheapflights partnered with top experts to bring you the best recommendations for your St. Louis to Chicago Midway Airport trip
Airports
STL

Security lines at STL are straightforward, typically taking 5-10 minutes off-peak. Check real-time wait times online before heading to the airport.

Read more about STLby Taryn White
MDW

The Orange Line train connects MDW to downtown Chicago in under 30 minutes, offering a convenient and affordable transportation option.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

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

Taryn White

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

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 month to book a flight from St. Louis to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from St. Louis to Chicago Midway Airport (average of $160). Flying from St. Louis to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 August 14, 2025.

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 in the evening, which can drop the price by up to 11% versus a flight in the afternoon.

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 August 10, 2025.

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

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 August 14, 2025.
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
4,244 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

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

    Currently priced at $151, 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 50% 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 $45. On average you can expect to pay $332. The most popular route, (Lambert-St Louis - Chicago Midway), can usually be booked for $77.

  • 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.

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

    Currently, April is the cheapest month in which you can book a flight from St. Louis to Chicago Midway Airport (average of $160). Flying from St. Louis to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$151Average$289FlexibilityNo cancel feeOn-time63%

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