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Midway

$49+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
STL — MDW
Nov 16 — Nov 231
Sun 11/16
Sun 11/23
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 October 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

April

Cheapest in

August

Average price

$271

Good round-trip deal

$273 or less

Good one-way deal

$104 or less
Provider with most accurate pricing for Lambert-St Louis-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Lambert-St Louis-Chicago (CHI) flights.
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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 ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 17, 2025.

This Southwest deal was found by Cheapflights users on 10/16. 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 11/135:45 pmSTL - MDW
Nonstop1h 10mSouthwest
Mon 11/176:20 amMDW - STL
Nonstop1h 15mSouthwest
Deal found 10/16$97
This Southwest deal was found by Cheapflights users on 10/16. 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 11/2010:20 amSTL - MDW
1 stop3h 35mSouthwest
Mon 11/246:45 amMDW - STL
Nonstop1h 15mSouthwest
Deal found 10/16$104
This Southwest deal was found by Cheapflights users on 10/15. 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 11/1810:35 amSTL - MDW
2 stops6h 15mSouthwest
Wed 11/195:15 pmMDW - STL
Nonstop1h 15mSouthwest
Deal found 10/15$112
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Thu 11/1311:07 amSTL - MDW
1 stop7h 32mFrontier
Sat 11/151:37 pmMDW - STL
1 stop20h 35mFrontier
Deal found 10/15$131
This Southwest deal was found by Cheapflights users on 10/15. 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 11/224:20 pmSTL - MDW
Nonstop1h 10mSouthwest
Mon 11/248:10 amMDW - STL
1 stop6h 05mSouthwest
Deal found 10/15$141
This Southwest deal was found by Cheapflights users on 10/15. 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 11/137:50 amSTL - MDW
1 stop4h 55mSouthwest
Sat 11/152:40 pmMDW - STL
Nonstop1h 10mSouthwest
Deal found 10/15$144
This Delta deal was found by Cheapflights users on 10/16. 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 11/126:00 amSTL - MDW
1 stop5h 52mDelta
Wed 11/196:00 amMDW - STL
1 stop4h 43mDelta
Deal found 10/16$157
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Thu 11/611:12 amMCI - MDW
1 stop10h 51mFrontier
Wed 11/122:06 pmMDW - MCI
1 stop20h 11mFrontier
Deal found 10/15$175
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
Thu 11/138:28 pmMCI - MDW
1 stop15h 02mFrontier
Sun 11/166:06 pmMDW - MCI
2 stops16h 11mFrontier
Deal found 10/16$179
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Wed 11/56:49 pmMCI - MDW
1 stop16h 41mMultiple Airlines
Tue 11/116:26 pmMDW - MCI
2 stops18h 02mMultiple Airlines
Deal found 10/15$180
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Mon 11/1011:12 amMCI - MDW
1 stop7h 27mMultiple Airlines
Tue 11/116:26 pmMDW - MCI
2 stops18h 02mMultiple Airlines
Deal found 10/15$183
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/311:12 amMCI - MDW
1 stop7h 27mFrontier
Sat 11/81:37 pmMDW - MCI
1 stop20h 40mFrontier
Deal found 10/14$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 October 17, 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

Thu 11/13

5:45 pm-6:55 pm

Nonstop1h 10m

Chicago Midway

Mon 11/17

6:20 am-7:35 am

Nonstop1h 15m

$97

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 11/20

10:20 am-1:55 pm

1 stop3h 35m

Chicago Midway

Mon 11/24

6:45 am-8:00 am

Nonstop1h 15m

$104

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Tue 11/18

10:35 am-4:50 pm

2 stops6h 15m

Chicago Midway

Wed 11/19

5:15 pm-6:30 pm

Nonstop1h 15m

$112

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 1/22

1:15 pm-2:20 pm

Nonstop1h 05m

Chicago Midway

Sat 1/24

7:40 pm-8:55 pm

Nonstop1h 15m

$134

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 11/22

4:20 pm-5:30 pm

Nonstop1h 10m

Chicago Midway

Mon 11/24

8:10 am-2:15 pm

1 stop6h 05m

$141

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sat 1/24

5:50 pm-7:00 pm

Nonstop1h 10m

Chicago Midway

Mon 2/2

2:35 pm-6:20 pm

1 stop3h 45m

$144

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 11/13

7:50 am-12:45 pm

1 stop4h 55m

Chicago Midway

Sat 11/15

2:40 pm-3:50 pm

Nonstop1h 10m

$144

SpringfieldChicago

SGF - MDW

SGFMDW

Springfield-Branson

Thu 11/13

6:58 pm-11:40 pm

1 stop4h 42m

Chicago Midway

Tue 11/18

12:47 pm-6:18 pm

1 stop5h 31m

$209

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Fri 11/14

11:12 am-6:39 pm

1 stop7h 27m

Chicago Midway

Sun 11/16

6:15 am-10:17 am

1 stop28h 02m

$209

SpringfieldChicago

SGF - MDW

SGFMDW

Springfield-Branson

Sat 11/15

4:02 pm-11:40 pm

1 stop7h 38m

Chicago Midway

Tue 11/18

10:47 am-3:17 pm

1 stop4h 30m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 43 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, November is the cheapest month in which you can book a flight from Missouri to Chicago Midway Airport (average of $82). Flying from Missouri to Chicago Midway Airport in January is currently the most expensive (average of $232). 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 October 17, 2025.

When flying from Missouri 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 8% versus a flight in the afternoon.

What is the cheapest day to fly from Missouri to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Missouri to Midway. Price data was last updated on November 3, 2024.

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

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.

  • How long is the flight from Missouri to Chicago Midway Airport?

    For as low as $97, Southwest can have you in Chicago Midway Airport from Missouri in 1h 10m. There are 251 mi between Missouri and Chicago Midway Airport. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $48. On average you can expect to pay $288. The most popular route, (Kansas City - Chicago Midway), can usually be booked for $231.

  • 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, November is the cheapest month in which you can book a flight from Missouri to Chicago Midway Airport (average of $82). Flying from Missouri to Chicago Midway Airport in January is currently the most expensive (average of $232). 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
Porter
Benton Harbor
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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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 October 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$137Average$326FlexibilityNo cancel feeOn-time63%

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