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Midway

$32+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
STL — MDW
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
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 December 4, 2025.

This Delta deal was found by Cheapflights users on 12/2. 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.
Thu 12/256:05 amSTL - MDW
1 stop5h 01mDelta
Thu 1/87:16 pmMDW - STL
1 stop4h 09mDelta
Deal found 12/2$157
This Southwest deal was found by Cheapflights users on 12/2. 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 12/251:50 pmSTL - MDW
Nonstop1h 05mSouthwest
Thu 1/87:45 pmMDW - STL
Nonstop1h 15mSouthwest
Deal found 12/2$165
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/2510:42 amSTL - MDW
1 stop6h 56mFrontier
Wed 12/316:12 amMDW - STL
1 stop27h 28mFrontier
Deal found 12/3$194
This Frontier deal was found by Cheapflights users on 12/1. 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.
Mon 12/810:47 amSTL - MDW
1 stop11h 25mFrontier
Thu 12/113:10 pmMDW - STL
1 stop7h 23mFrontier
Deal found 12/1$208
This Delta deal was found by Cheapflights users on 12/4. 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 12/1712:49 pmSTL - MDW
1 stop5h 29mDelta
Sat 1/105:00 pmMDW - STL
1 stop6h 25mDelta
Deal found 12/4$217
This Frontier deal was found by Cheapflights users on 12/3. 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.
Sun 12/2110:57 amSTL - MDW
1 stop11h 15mFrontier
Sun 1/410:50 pmMDW - STL
1 stop11h 12mFrontier
Deal found 12/3$218
This Booking.com deal was found by Cheapflights users on 12/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:30 pmSTL - MDW
1 stop6h 28mFrontier
Fri 12/1212:18 pmMDW - STL
1 stop21h 56mFrontier
Deal found 12/3$220
This Frontier deal was found by Cheapflights users on 12/3. 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.
Fri 12/123:30 pmSTL - MDW
1 stop7h 09mFrontier
Sun 1/116:10 amMDW - STL
1 stop8h 38mFrontier
Deal found 12/3$222
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/1210:42 amSTL - MDW
2 stops11h 57mFrontier
Tue 1/1311:39 amMDW - STL
1 stop19h 12mFrontier
Deal found 12/2$228
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/1810:42 amSTL - MDW
1 stop11h 30mFrontier
Wed 12/316:12 amMDW - STL
1 stop27h 28mFrontier
Deal found 12/3$229
This Frontier deal was found by Cheapflights users on 12/3. 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.
Sun 12/1410:42 amSTL - MDW
1 stop7h 30mFrontier
Sun 12/2110:50 pmMDW - STL
1 stop11h 12mFrontier
Deal found 12/3$232
This Southwest deal was found by Cheapflights users on 12/2. 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 12/311:35 pmMCI - MDW
1 stop3h 35mSouthwest
Thu 1/18:10 amMDW - MCI
Nonstop1h 35mSouthwest
Deal found 12/2$241

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 December 4, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$88
(Southwest)

One-way from

$32
(Southwest)

Popular in

November

Cheapest in

August

Average price

$266

Good round-trip deal

$307 or less

Good one-way deal

$184 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. 7% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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.
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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 December 4, 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 1/17

5:50 pm-7:00 pm

Nonstop1h 10m

Chicago Midway

Sun 1/18

9:55 am-11:15 am

Nonstop1h 20m

$88

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 1/8

6:05 am-7:15 am

Nonstop1h 10m

Chicago Midway

Mon 1/12

7:45 pm-9:00 pm

Nonstop1h 15m

$91

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Wed 2/18

8:15 am-1:25 pm

1 stop5h 10m

Chicago Midway

Sat 2/21

7:45 am-9:05 am

Nonstop1h 20m

$128

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 1/8

3:43 pm-10:17 pm

1 stop6h 34m

Chicago Midway

Mon 1/12

4:31 pm-10:34 pm

1 stop30h 03m

$156

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Fri 1/16

6:35 am-12:48 pm

1 stop6h 13m

Chicago Midway

Fri 1/23

7:16 pm-11:23 pm

1 stop4h 07m

$157

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 1/8

6:00 am-10:27 am

1 stop4h 27m

Chicago Midway

Mon 1/12

7:16 pm-11:25 pm

1 stop4h 09m

$157

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Thu 12/25

6:05 am-11:06 am

1 stop5h 01m

Chicago Midway

Thu 1/8

7:16 pm-11:25 pm

1 stop4h 09m

$157

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Fri 2/27

3:47 pm-10:42 pm

1 stop6h 55m

Chicago Midway

Sun 3/1

7:17 pm-11:23 pm

1 stop4h 06m

$161

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Sun 2/15

6:35 am-12:46 pm

1 stop6h 11m

Chicago Midway

Sun 2/15

5:00 pm-11:23 pm

1 stop6h 23m

$165

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

Fri 1/16

6:10 am-12:48 pm

2 stops6h 38m

Chicago Midway

Mon 1/19

10:46 am-5:50 pm

1 stop7h 04m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 56 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 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 December 4, 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 13% versus a flight at noon.

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 December 16, 2024.

Travelers seeking maximum savings on their Missouri to Chicago Midway Airport flight should consider departing on Tuesday 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 $88, 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 $126. On average you can expect to pay $294. The most popular route, (Kansas City - Chicago Midway), can usually be booked for $109.

  • 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 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
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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Boston to Midway 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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$328FlexibilityNo cancel feeOn-time63%

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