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Midway

$52+ Cheap flights from Missouri 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
STL — MDW
Aug 12 — Aug 191
Tue 8/12
Tue 8/19
1 adult, Economy
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Cheap flight deals from Missouri to Midway

Keep the following information in mind while searching for Missouri to Midway flight deals. Data was last updated August 7, 2025.

Round-trip from

$85
(Southwest)

One-way from

$52
(Southwest)

Popular in

March

Cheapest in

September

Average price

$279

Good round-trip deal

$236 or less

Good one-way deal

$118 or less
From Missouri to Chicago Midway
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One-way flight from Missouri to Chicago Midway
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Highest demand for flights based on searches. 7% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 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 Missouri to Chicago Midway.
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Price to beat on a one-way flight from Missouri to Chicago Midway.
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Find flight deals from Missouri to Midway

Cheapest flights from Missouri to Midway
Explore the most affordable flight options available from Missouri to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 7, 2025.

This Southwest deal was found by Cheapflights users on 8/6. 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 9/66:00 pmSTL - MDW
Nonstop1h 05mSouthwest
Mon 9/82:35 pmMDW - STL
Nonstop1h 10mSouthwest
Deal found 8/6$85
This Southwest deal was found by Cheapflights users on 8/6. 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 9/61:45 pmSTL - MDW
Nonstop1h 05mSouthwest
Sat 9/63:55 pmMDW - STL
Nonstop1h 15mSouthwest
Deal found 8/6$91
This Southwest deal was found by Cheapflights users on 8/6. 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 9/66:00 pmSTL - MDW
Nonstop1h 05mSouthwest
Sun 9/77:25 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 8/6$97
This Southwest deal was found by Cheapflights users on 8/5. 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.
Mon 8/255:25 amSTL - MDW
Nonstop1h 10mSouthwest
Wed 8/275:40 pmMDW - STL
Nonstop1h 15mSouthwest
Deal found 8/5$103
This Southwest deal was found by Cheapflights users on 8/5. 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 9/217:30 amSTL - MDW
Nonstop1h 10mSouthwest
Wed 9/2411:25 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 8/5$109
This Southwest deal was found by Cheapflights users on 8/6. 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.
Mon 9/227:20 pmSTL - MDW
Nonstop1h 05mSouthwest
Fri 9/267:20 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 8/6$115
This Southwest deal was found by Cheapflights users on 8/5. 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.
Mon 8/257:20 pmSTL - MDW
Nonstop1h 05mSouthwest
Tue 9/26:25 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 8/5$121
This Southwest deal was found by Cheapflights users on 8/5. 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 12/66:25 amSTL - MDW
Nonstop1h 10mSouthwest
Sun 12/79:40 pmMDW - STL
Nonstop1h 15mSouthwest
Deal found 8/5$122
This Southwest deal was found by Cheapflights users on 8/5. 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 9/287:30 amSTL - MDW
Nonstop1h 10mSouthwest
Wed 10/19:55 amMDW - STL
1 stop3h 55mSouthwest
Deal found 8/5$125
This Southwest deal was found by Cheapflights users on 8/6. 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.
Tue 9/304:35 pmSTL - MDW
Nonstop1h 10mSouthwest
Fri 10/39:40 amMDW - STL
Nonstop1h 15mSouthwest
Deal found 8/6$127
This Southwest deal was found by Cheapflights users on 8/5. 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.
Mon 8/255:25 amSTL - MDW
Nonstop1h 10mSouthwest
Tue 8/268:25 pmMDW - STL
Nonstop1h 15mSouthwest
Deal found 8/5$128
This Southwest deal was found by Cheapflights users on 8/6. 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.
Mon 10/65:35 amMCI - MDW
2 stops5h 50mSouthwest
Tue 10/75:35 pmMDW - MCI
Nonstop1h 30mSouthwest
Deal found 8/6$184

Cheapflights Fare Finder

 
Customize your flight search to find flights from Missouri 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 7, 2025.
Use the filters below to find and compare flights from Missouri to Chicago Midway Airport that are best for you.

Fly from

Missouri

Fly to

Midway

Route

Depart

Return

Price

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 9/6

6:00 pm-7:05 pm

Nonstop1h 05m

Chicago Midway

Mon 9/8

2:35 pm-3:45 pm

Nonstop1h 10m

$85

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 9/6

1:45 pm-2:50 pm

Nonstop1h 05m

Chicago Midway

Sat 9/6

3:55 pm-5:10 pm

Nonstop1h 15m

$91

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 9/6

6:00 pm-7:05 pm

Nonstop1h 05m

Chicago Midway

Sun 9/7

7:25 am-8:35 am

Nonstop1h 10m

$97

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Mon 8/25

5:25 am-6:35 am

Nonstop1h 10m

Chicago Midway

Wed 8/27

5:40 pm-6:55 pm

Nonstop1h 15m

$103

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sun 9/21

7:30 am-8:40 am

Nonstop1h 10m

Chicago Midway

Wed 9/24

11:25 am-12:35 pm

Nonstop1h 10m

$109

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Mon 9/22

7:20 pm-8:25 pm

Nonstop1h 05m

Chicago Midway

Fri 9/26

7:20 am-8:30 am

Nonstop1h 10m

$115

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Mon 8/25

7:20 pm-8:25 pm

Nonstop1h 05m

Chicago Midway

Tue 9/2

6:25 am-7:35 am

Nonstop1h 10m

$121

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sun 9/28

7:30 am-8:40 am

Nonstop1h 10m

Chicago Midway

Wed 10/1

9:55 am-1:50 pm

1 stop3h 55m

$125

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Tue 9/30

4:35 pm-5:45 pm

Nonstop1h 10m

Chicago Midway

Fri 10/3

9:40 am-10:55 am

Nonstop1h 15m

$127

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Mon 8/25

5:25 am-6:35 am

Nonstop1h 10m

Chicago Midway

Tue 8/26

8:25 pm-9:40 pm

Nonstop1h 15m

$128

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/7

Showing 1-10 of 54 results
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Best time to book a flight from Missouri to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Missouri 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 Missouri to Chicago Midway Airport

What is the cheapest month to book a flight from Missouri to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Missouri to Chicago Midway Airport (average of $160). Flying from Missouri 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 MO to MDW?

Find hourly flight availability from Missouri 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 7, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Missouri to Chicago Midway Airport as you normally would.

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 7, 2025.
See what other customers who have flown with Southwest, Delta, and Frontier from Missouri to Chicago Midway Airport have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,247 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,987 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,230 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

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

  • What are the most popular routes from Missouri to Chicago Midway Airport?

    The most popular route from Missouri to Chicago Midway Airport is Kansas City - Chicago Midway. You may also consider Lambert-St Louis - Chicago Midway or Springfield-Branson - Chicago Midway.

  • What are the cheapest flights from Missouri to Chicago Midway Airport?

    The cheapest flight price from Missouri to Chicago Midway Airport is $30. On average you can expect to pay $333. The most popular route, (Kansas City - Chicago Midway), can usually be booked for $105.

  • Can I find deals for flights from Missouri to Midway that include hotel bookings?

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

  • How can I find direct flights from Missouri to Midway?

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

  • Can I find deals for business class flights from Missouri to Midway?

    Yes. Cheapflights offers flight deals from Missouri 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 Missouri to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Missouri to Chicago Midway Airport (average of $160). Flying from Missouri 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
Valparaiso
Chesterton

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Alternative routes for Missouri to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Boston to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Seattle to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Dallas/Fort Worth to Midway flights
Philadelphia to O'Hare Intl flights
Newark to Midway flights
Hobby to O'Hare Intl flights
LaGuardia to Midway flights
Ontario to O'Hare Intl flights
Denver to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Austin to O'Hare Intl flights
Dulles Intl to Midway flights
Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
San Francisco to Midway flights
Hobby to Midway flights
Atlanta to O'Hare Intl flights
Charlotte to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Los Angeles to Midway flights
Atlanta to Midway flights
Burbank to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
San Jose to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Love Field to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Portland to O'Hare Intl flights
Baltimore to Midway flights
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Love Field to Midway flights
Seattle to Midway flights
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San Diego to O'Hare Intl flights
Minneapolis to Midway flights
Boston to Midway flights
Oakland to O'Hare Intl flights
Tampa to O'Hare Intl flights
Charleston to O'Hare Intl flights

Top airline flying from Missouri to Midway

Discover the top airline that operate flights from Missouri 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 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$151Average$306FlexibilityNo cancel feeOn-time63%

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