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$80+ 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 3/21. Fares are subject to change and may not be available on all flights or dates of travel.
MCI — MDW
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap 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 December 28, 2025.

This Trip.com deal was found by Cheapflights users on 12/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:33 amMCI - MDW
1 stop10h 39mFrontier
Sun 1/410:50 pmMDW - MCI
1 stop21h 00mFrontier
Deal found 12/26$476
This Southwest deal was found by Cheapflights users on 12/27. 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 12/281:45 pmMCI - MDW
Nonstop1h 20mSouthwest
Sat 1/242:30 pmMDW - MCI
Nonstop1h 30mSouthwest
Deal found 12/27$500
This Trip.com deal was found by Cheapflights users on 12/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/278:45 pmMCI - MDW
1 stop25h 05mFrontier
Tue 12/302:01 pmMDW - MCI
1 stop5h 49mFrontier
Deal found 12/26$602
This Kiwi.com deal was found by Cheapflights users on 12/25. 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 12/298:45 pmMCI - MDW
1 stop23h 10mMultiple Airlines
Wed 12/313:10 pmMDW - MCI
1 stop7h 49mMultiple Airlines
Deal found 12/25$677
This Southwest deal was found by Cheapflights users on 12/26. 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 12/313:30 pmMCI - MDW
Nonstop1h 25mSouthwest
Sun 1/46:35 pmMDW - MCI
Nonstop1h 35mSouthwest
Deal found 12/26$681
This Southwest deal was found by Cheapflights users on 12/27. 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 12/2712:35 pmMCI - MDW
Nonstop1h 20mSouthwest
Mon 12/2912:05 pmMDW - MCI
Nonstop1h 25mSouthwest
Deal found 12/27$688
This Southwest deal was found by Cheapflights users on 12/25. 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 12/268:10 amMCI - MDW
2 stops6h 40mSouthwest
Fri 1/28:15 amMDW - MCI
Nonstop1h 35mSouthwest
Deal found 12/25$696

Find 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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$236
(Kiwi.com)

One-way from

$80
(Southwest)

Popular in

June

Cheapest in

April

Average price

$374
Provider with most accurate pricing for Kansas City-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Kansas City-Chicago Midway flights.
Search Deals
From Kansas City to Chicago Midway
Search Deals
One-way flight from Kansas City to Chicago Midway
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($5 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 28, 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

Thu 1/15

3:35 pm-7:45 pm

1 stop4h 10m

Chicago Midway

Sun 1/18

6:00 am-10:20 am

1 stop4h 20m

$238

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Thu 2/5

3:35 pm-5:00 pm

Nonstop1h 25m

Chicago Midway

Mon 2/9

8:35 pm-10:10 pm

Nonstop1h 35m

$239

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Thu 3/12

6:00 pm-12:05 am

1 stop6h 05m

Chicago Midway

Mon 3/16

6:30 pm-8:00 pm

Nonstop1h 30m

$261

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Sun 2/15

6:05 pm-7:30 pm

Nonstop1h 25m

Chicago Midway

Tue 2/24

10:05 am-11:40 am

Nonstop1h 35m

$261

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Sat 3/14

5:20 pm-11:50 pm

1 stop6h 30m

Chicago Midway

Wed 3/18

7:35 am-9:05 am

Nonstop1h 30m

$261

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Fri 3/13

5:50 pm-11:35 pm

1 stop5h 45m

Chicago Midway

Mon 3/16

7:45 am-9:15 am

Nonstop1h 30m

$261

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Sat 1/17

6:30 am-4:16 pm

2 stops9h 46m

Chicago Midway

Sun 1/18

6:45 am-12:44 pm

1 stop5h 59m

$263

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Thu 2/5

6:30 am-6:36 pm

2 stops12h 06m

Chicago Midway

Mon 2/9

9:33 am-8:02 pm

2 stops10h 29m

$269

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Thu 3/12

6:07 am-12:29 pm

2 stops6h 22m

Chicago Midway

Tue 3/17

7:20 pm-11:03 pm

1 stop3h 43m

$270

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Sat 3/21

4:15 pm-5:40 pm

Nonstop1h 25m

$80

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/28

Showing 1-10 of 21 results
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Compare providers for flights from Kansas City to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Kansas City to Midway in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Kansas City-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Kansas City-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Kansas City-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Kansas City-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Kansas City-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, October is the cheapest month in which you can book a flight from Kansas City to Chicago Midway Airport (average of $173). Flying from Kansas City to Chicago Midway Airport in February is currently the most expensive (average of $267). 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 December 28, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 18% 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 December 20, 2025.

Travelers seeking maximum savings on their Kansas City 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.

The best insider tips for Kansas City to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
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

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 December 28, 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
4,256 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 3 outbound flights to Chicago Midway per day.

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

    Airlines like Southwest fly from Kansas City to Chicago Midway Airport in about 4h 10m. The time it takes to get you to your destination can typically vary by up to . The distance from Kansas City to Chicago Midway Airport is about 404 mi.

  • 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 $214. Users have found that Southwest is 38% 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 $166. On average you can expect to pay $340. The most popular route, (Kansas City - Chicago Midway), can usually be booked for $213.

  • 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, October is the cheapest month in which you can book a flight from Kansas City to Chicago Midway Airport (average of $173). Flying from Kansas City to Chicago Midway Airport in February is currently the most expensive (average of $267). 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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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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$214Average$345FlexibilityNo cancel feeOn-time63%

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