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Midway

$100+ Cheap flights from Kansas City (MCI) 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
MCI — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Kansas City to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Kansas City (MCI) 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

$185
(Southwest)

One-way from

$100
(Southwest)

Popular in

June

Cheapest in

April

Average price

$319
From Kansas City to Chicago Midway
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One-way flight from Kansas City to Chicago Midway
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Highest demand for flights based on searches. 5% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Kansas City to Midway

Cheapest flights from Kansas City to Midway
Explore the most affordable flight options available from Kansas City 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 8/13. 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.
Wed 9/247:00 amMCI - MDW
Nonstop1h 25mSouthwest
Wed 9/242:10 pmMDW - MCI
Nonstop1h 25mSouthwest
Deal found 8/13$185
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.
Sat 10/113:25 pmMCI - MDW
1 stop4h 55mSouthwest
Tue 10/145:50 amMDW - MCI
1 stop6h 00mSouthwest
Deal found 8/13$186
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 9/44:10 pmMCI - MDW
Nonstop1h 25mSouthwest
Mon 9/85:40 pmMDW - MCI
1 stop6h 25mSouthwest
Deal found 8/14$187
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 9/58:25 pmMCI - MDW
Nonstop1h 20mSouthwest
Mon 9/88:40 pmMDW - MCI
Nonstop1h 25mSouthwest
Deal found 8/14$188
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/53:01 pmMCI - MDW
2 stops19h 27mFrontier
Mon 9/86:20 amMDW - MCI
1 stop10h 00mFrontier
Deal found 8/14$189
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1311:12 amMCI - MDW
1 stop7h 27mFrontier
Sun 11/1612:30 pmMDW - MCI
1 stop7h 03mFrontier
Deal found 8/14$190
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.
Sat 11/1510:35 amMCI - MDW
2 stops6h 05mSouthwest
Tue 11/188:25 amMDW - MCI
1 stop3h 05mSouthwest
Deal found 8/13$191
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.
Wed 9/39:10 amMCI - MDW
2 stops6h 10mSouthwest
Sat 9/131:20 pmMDW - MCI
Nonstop1h 25mSouthwest
Deal found 8/13$192
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.
Tue 9/2312:35 pmMCI - MDW
Nonstop1h 25mSouthwest
Sat 9/277:25 pmMDW - MCI
Nonstop1h 25mSouthwest
Deal found 8/13$193
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/911:37 amMCI - MDW
1 stop8h 44mFrontier
Mon 10/1310:31 amMDW - MCI
1 stop9h 22mFrontier
Deal found 8/14$196
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/276:30 amMCI - MDW
1 stop6h 33mDelta
Sat 10/46:15 pmMDW - MCI
1 stop3h 52mDelta
Deal found 8/12$197

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kansas City 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 Kansas City to Chicago Midway Airport that are best for you.

Fly from

Kansas City

Fly to

Midway

Route

Depart

Return

Price

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Wed 9/24

7:00 am-8:25 am

Nonstop1h 25m

Chicago Midway

Wed 9/24

2:10 pm-3:35 pm

Nonstop1h 25m

$185

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Sat 10/11

3:25 pm-8:20 pm

1 stop4h 55m

Chicago Midway

Tue 10/14

5:50 am-11:50 am

1 stop6h 00m

$186

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Tue 9/23

4:55 pm-9:30 pm

1 stop4h 35m

Chicago Midway

Sat 9/27

8:20 am-3:55 pm

1 stop7h 35m

$186

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Mon 9/8

5:30 pm-8:25 pm

1 stop2h 55m

Chicago Midway

Wed 9/10

9:00 am-2:10 pm

1 stop5h 10m

$186

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Wed 9/10

7:30 pm-8:50 pm

Nonstop1h 20m

Chicago Midway

Fri 9/12

11:45 am-3:55 pm

1 stop4h 10m

$187

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Wed 10/22

10:40 am-2:25 pm

1 stop3h 45m

Chicago Midway

Sun 10/26

7:20 am-8:45 am

Nonstop1h 25m

$187

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Mon 9/15

8:25 pm-9:45 pm

Nonstop1h 20m

Chicago Midway

Thu 9/18

6:30 am-10:55 am

1 stop4h 25m

$187

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Mon 10/6

7:10 pm-12:45 am

1 stop5h 35m

Chicago Midway

Thu 10/9

10:25 pm-11:55 pm

Nonstop1h 30m

$187

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Sat 9/6

2:50 pm-4:15 pm

Nonstop1h 25m

Chicago Midway

Mon 9/8

7:40 am-2:00 pm

1 stop6h 20m

$187

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Sat 10/4

10:15 am-11:40 am

Nonstop1h 25m

Chicago Midway

Sat 10/4

1:25 pm-6:55 pm

1 stop5h 30m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 17 results
1
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The best insider tips for Kansas City 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 Kansas City to Chicago Midway Airport trip
Airports
MCI

MCI's central security checkpoint rarely has long waits, with lines typically under 5 minutes even without TSA PreCheck.

Read more about MCIby Matt Meltzer
MDW

The Orange Line train is a cheap, convenient way to reach downtown Chicago from MDW, taking less than 30 minutes.

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
Matt Meltzer

Matt Meltzer

Expert on MCI

Matt Meltzer

Matt Meltzer

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more

Best time to book a flight from Kansas City to Midway

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

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

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

Find hourly flight availability from Kansas City 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.

Unlike in the morning, when flights are generally more expensive, you can save up to 20% on flights from Kansas City to Chicago Midway Airport by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Kansas City to Midway. Price data was last updated on August 10, 2025.

Travelers seeking maximum savings on their Kansas City 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.

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 Kansas City 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

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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 Kansas City 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 Kansas City to Chicago Midway?

    Kansas City (MCI), located 17.4 mi from the city center, is the airport you fly out of when you book flights from Kansas City to Chicago Midway. 1 airline have flights from Kansas City to Chicago Midway on a regular basis. Booking flights from Kansas City to Chicago Midway should not be difficult; the airport handles an average of 5 outbound flights to Chicago Midway per day.

  • What is the cheapest airline to fly from Kansas City to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Kansas City to Chicago Midway Airport round-trip from $206. Users have found that Southwest is 37% cheaper than the other options available to this destination.

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

    The cheapest flight price from Kansas City to Chicago Midway Airport is $118. On average you can expect to pay $305. The most popular route, (Kansas City - Chicago Midway), can usually be booked for $155.

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

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

  • How can I find direct flights from Kansas City to Midway?

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

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

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

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

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Kansas City to Midway

Discover the top airline that operate flights from Kansas City 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$206Average$326FlexibilityNo cancel feeOn-time63%

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