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Midway

$67+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
STL — MDW
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap 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 January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/20. 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 1/288:22 pm
STL
-
MDW
1 stop15h 23m
Frontier
Fri 1/305:01 pm
MDW
-
STL
1 stop13h 50m
Frontier
Deal found 1/20$156
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Fri 1/308:22 pm
STL
-
MDW
1 stop12h 21m
Frontier
Sun 2/16:20 am
MDW
-
STL
1 stop24h 31m
Frontier
Deal found 1/20$158
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/188:17 pm
STL
-
MDW
1 stop15h 10m
Frontier
Wed 2/257:00 am
MDW
-
STL
2 stops15h 27m
Frontier
Deal found 1/19$175
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/168:22 pm
STL
-
MDW
1 stop22h 45m
Frontier
Mon 2/239:22 pm
MDW
-
STL
1 stop25h 05m
Frontier
Deal found 1/19$188
This Frontier deal was found by Cheapflights users on 1/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:32 am
STL
-
MDW
1 stop10h 47m
Frontier
Wed 3/1811:19 am
MDW
-
STL
1 stop12h 00m
Frontier
Deal found 1/19$190
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 3/48:17 pm
STL
-
MDW
1 stop19h 59m
Frontier
Fri 3/66:05 am
MDW
-
STL
1 stop5h 44m
Frontier
Deal found 1/20$191
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/2310:55 am
MCI
-
MDW
1 stop8h 52m
Frontier
Thu 2/265:16 pm
MDW
-
MCI
1 stop16h 40m
Frontier
Deal found 1/19$192
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Tue 2/173:49 pm
STL
-
MDW
2 stops27h 18m
Frontier
Tue 2/246:10 am
MDW
-
STL
1 stop24h 41m
Frontier
Deal found 1/19$193
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/2310:55 am
MCI
-
MDW
1 stop8h 52m
Multiple Airlines
Mon 3/29:22 pm
MDW
-
MCI
1 stop18h 07m
Multiple Airlines
Deal found 1/19$194
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Fri 2/2011:00 am
MCI
-
MDW
1 stop11h 25m
Frontier
Sun 2/229:04 pm
MDW
-
MCI
1 stop12h 49m
Frontier
Deal found 1/19$200
This Southwest deal was found by Cheapflights users on 1/18. 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 4/225:30 am
MCI
-
MDW
1 stop6h 25m
Southwest
Wed 4/222:30 pm
MDW
-
MCI
Nonstop1h 30m
Southwest
Deal found 1/18$201
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 3/28:33 pm
MCI
-
MDW
2 stops22h 34m
Frontier
Mon 3/96:00 am
MDW
-
MCI
1 stop10h 20m
Frontier
Deal found 1/19$205

Find flight deals from Missouri to Midway

Keep the following information in mind while searching for Missouri to Midway flight deals. Data was last updated January 21, 2026.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$156
(Kiwi.com)

One-way from

$67
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$254

Good round-trip deal

$328 or less

Good one-way deal

$166 or less
Provider with most accurate pricing for Lambert-St Louis-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Lambert-St Louis-Chicago (CHI) flights.
Search Deals
From Missouri to Chicago Midway
Search Deals
One-way flight from Missouri to Chicago Midway
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Missouri to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Missouri to Chicago Midway.
Search Deals

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 January 21, 2026.
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

SpringfieldChicago

SGF - MDW

SGFMDW

Springfield-Branson

Thu 2/12

5:32 pm-10:31 pm

1 stop4h 59m

Chicago Midway

Thu 2/19

10:49 am-4:47 pm

1 stop5h 58m

$209

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Tue 2/17

7:30 am-12:55 pm

1 stop5h 25m

Chicago Midway

Wed 2/18

9:50 am-5:30 pm

1 stop7h 40m

$211

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Tue 2/10

10:55 am-4:40 pm

1 stop5h 45m

Chicago Midway

Wed 2/11

12:10 pm-7:20 pm

1 stop7h 10m

$211

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Wed 2/18

3:25 pm-8:40 pm

1 stop5h 15m

Chicago Midway

Sat 2/21

12:50 pm-2:20 pm

Nonstop1h 30m

$221

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Tue 3/24

11:05 am-5:05 pm

1 stop6h 00m

Chicago Midway

Thu 3/26

7:45 am-9:15 am

Nonstop1h 30m

$224

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Sat 3/7

10:30 am-3:21 pm

1 stop4h 51m

Chicago Midway

Sat 3/14

9:30 am-3:19 pm

1 stop5h 49m

$234

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Sat 2/21

11:55 am-1:20 pm

Nonstop1h 25m

Chicago Midway

Mon 2/23

3:10 pm-4:40 pm

Nonstop1h 30m

$234

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Mon 3/2

6:05 pm-7:30 pm

Nonstop1h 25m

Chicago Midway

Mon 3/9

10:10 am-11:40 am

Nonstop1h 30m

$237

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Mon 3/9

1:50 pm-3:10 pm

Nonstop1h 20m

Chicago Midway

Thu 3/12

10:10 am-11:40 am

Nonstop1h 30m

$237

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Wed 2/18

6:40 am-1:10 pm

1 stop6h 30m

Chicago Midway

Wed 2/25

2:20 pm-9:30 pm

1 stop7h 10m

$242

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 57 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 $77). Flying from Missouri to Chicago Midway Airport in December is currently the most expensive (average of $240). 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 January 21, 2026.

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 15% versus a flight in the morning.

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 January 17, 2026.

Travelers seeking maximum savings on their Missouri to Chicago Midway Airport flight should consider departing on Tuesday at noon 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 $209, Delta can have you in Chicago Midway Airport from Missouri in 4h 59m. There are 434 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 $128. On average you can expect to pay $311. The most popular route, (Kansas City - Chicago Midway), can usually be booked for $191.

  • 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 $77). Flying from Missouri to Chicago Midway Airport in December is currently the most expensive (average of $240). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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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Philadelphia to Midway flights
Miami to O'Hare Intl flights
Denver to Midway flights
Cleveland to O'Hare Intl flights
Detroit to O'Hare Intl flights
Minneapolis to Midway flights
Reagan-National to Midway flights
Sacramento to O'Hare Intl flights
San Jose to O'Hare Intl flights
Nashville to O'Hare Intl flights
San Antonio 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$335FlexibilityNo cancel feeOn-time63%

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