Midway

$130+ Cheap flights from Kansas City (MCI) to Midway (MDW)

MCI — MDW
Dec 10 — Dec 171
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kansas City to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Kansas City to Chicago Midway are usually found in December or November, booked 29 days in advance, depart on a Wednesday or Thursday and return on a Saturday

Cheap flight deals from Kansas City to Midway

Cheapest flights from Kansas City to Midway

Wed 12/22:40 pm -
Nonstop1h 30m
Wed 12/911:45 am -
Nonstop1h 30m
Deal found 11/4$237
Thu 11/2611:00 am -
1 stop5h 50m
Thu 12/38:10 am -
Nonstop1h 40m
Deal found 11/5$247
Wed 12/210:38 am -
1 stop6h 12m
Wed 12/95:30 pm -
1 stop5h 58m
Deal found 11/4$257
Wed 12/28:00 am -
Nonstop1h 25m
Wed 12/211:45 am -
Nonstop1h 30m
Deal found 11/6$259
Wed 12/306:05 pm -
1 stop4h 55m
Tue 1/53:45 pm -
2 stops6h 25m
Deal found 11/5$262
Fri 12/1110:30 am -
1 stop6h 46m
Sun 12/138:37 pm -
1 stop12h 58m
Deal found 11/5$263
Sat 12/511:30 am -
Nonstop1h 25m
Mon 12/710:05 am -
Nonstop1h 30m
Deal found 11/9$274
Tue 12/812:20 pm -
1 stop5h 30m
Sat 12/125:05 am -
1 stop7h 15m
Deal found 11/7$279
Mon 11/2311:11 am -
1 stop8h 36m
Tue 11/248:42 pm -
1 stop13h 34m
Deal found 11/5$280
Thu 12/37:00 am -
1 stop5h 20m
Thu 12/1010:05 am -
Nonstop1h 30m
Deal found 11/5$283

Find flight deals from Kansas City to Midway

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Southwest)

One-way from

$130
(Southwest)

Popular in

March

Cheapest in

December

Average price

$399
Provider with most accurate pricing for Kansas City-Chicago Midway flight deals.
Provider most trusted by Cheapflights users for Kansas City-Chicago Midway flights.
From Kansas City to Chicago Midway
One-way flight from Kansas City to Chicago Midway
Highest demand for flights based on searches. 9% potential increase in price ($50 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Average for round-trip flights in November 2026

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Kansas City to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Sat 12/12

6:10 am-2:30 pm

2 stops8h 20m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$145
Quickest round-trip

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Fri 12/11

2:35 pm-4:00 pm

Nonstop1h 25m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$155

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Wed 11/25

11:11 am-7:47 pm

1 stop8h 36m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$163

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Tue 12/29

6:05 pm-11:00 pm

1 stop4h 55m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$165

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Wed 11/25

5:38 pm-12:21 pm

2 stops18h 43m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$199

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Sun 12/6

4:25 pm-5:50 pm

Nonstop1h 25m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$215

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Wed 11/25

5:10 am-6:35 am

Nonstop1h 25m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$237

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Sat 11/21

5:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$237

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Sat 11/14

1:10 pm-2:35 pm

Nonstop1h 25m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$237

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Mon 12/28

5:10 am-6:35 am

Nonstop1h 25m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$245

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Kansas City to Midway

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Kansas City-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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

Cheapflights Insights

Everything you need to know about your flight from Kansas City to Chicago Midway Airport

How far ahead should I book a flight from Kansas City to Chicago Midway Airport?

To ensure you get the cheapest price possible for a flight from Kansas City to Chicago Midway Airport, you should look to book at least 28 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, December is the cheapest month in which you can book a flight from Kansas City to Chicago Midway Airport (average of $329). Flying from Kansas City to Chicago Midway Airport in March is currently the most expensive (average of $601). 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?

Unlike in the morning, when flights are generally more expensive, you can save up to 17% 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?

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. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Kansas City to Chicago Midway Airport?

Airfare is below average for this route at the moment.

Kansas City to Chicago Midway Airport flights typically cost between $359 and $481 in December.
The cheapest round-trip price found within the last 5 days was $237 on Southwest (Dec 2-Dec 9).

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

Cheapflights partnered with top experts to bring you the best recommendations for your Kansas City to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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.

Matt Meltzer

Matt Meltzer

Expert on MCI

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.

Reviews of airlines servicing Midway

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.

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.4

Food

7.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.4

Food

7.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

  • 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 4 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 1h 25m. The time it takes to get you to your destination is usually consistent. The distance from Kansas City to Chicago Midway Airport is about 404 mi. Most flights are nonstop.

  • 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 $257. Users have found that Southwest is 44% 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 $354. The most popular route, (Kansas City - Chicago Midway), can usually be booked for $250.

  • 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, December is the cheapest month in which you can book a flight from Kansas City to Chicago Midway Airport (average of $329). Flying from Kansas City to Chicago Midway Airport in March is currently the most expensive (average of $601). 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
Benton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter

Browse thousands of different options on Cheapflights for your next trip

Top airline flying from Kansas City to Midway

AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$257Average$462FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.