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Cheap flights from Kansas City to Chicago from $129

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Kansas City to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
3:35 pm - 5:00 pmMCI  Kansas City-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
12:00 pm - 1:25 pmMDW  Chicago Midway-MCI Kansas City
1h 25mnonstop
$257Southwest
Wed, Sep 23 - Sat, Sep 26
Southwest Logo
5:30 am - 6:55 amMCI  Kansas City-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
2:25 pm - 3:50 pmMDW  Chicago Midway-MCI Kansas City
1h 25mnonstop
$257Southwest
Mon, Oct 5 - Thu, Oct 8
Southwest Logo
5:30 am - 6:55 amMCI  Kansas City-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
7:50 am - 9:20 amMDW  Chicago Midway-MCI Kansas City
1h 30mnonstop
$257Southwest
Mon, Oct 19 - Wed, Oct 21
Southwest Logo
8:00 am - 9:25 amMCI  Kansas City-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
10:05 am - 11:35 amMDW  Chicago Midway-MCI Kansas City
1h 30mnonstop
$257Southwest
Tue, Nov 17 - Thu, Nov 19
Southwest Logo
5:55 pm - 7:20 pmMCI  Kansas City-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
6:00 am - 7:30 amMDW  Chicago Midway-MCI Kansas City
1h 30mnonstop
$257Southwest
Wed, Sep 30 - Wed, Oct 7
Southwest Logo
8:10 pm - 9:35 pmMCI  Kansas City-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
7:30 am - 8:55 amMDW  Chicago Midway-MCI Kansas City
1h 25mnonstop
$257Southwest
Thu, Sep 24 - Mon, Sep 28
Southwest Logo
5:30 am - 6:55 amMCI  Kansas City-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
9:30 pm - 11:05 pmMDW  Chicago Midway-MCI Kansas City
1h 35mnonstop
$257Southwest
Thu, Oct 1 - Mon, Oct 5
Southwest Logo
5:55 pm - 7:20 pmMCI  Kansas City-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
12:05 pm - 1:30 pmMDW  Chicago Midway-MCI Kansas City
1h 25mnonstop
$257Southwest
Tue, Sep 29 - Tue, Oct 6
Delta Logo
6:30 am - 11:47 amMCI  Kansas City-MDW Chicago Midway
5h 17m1 stop Minneapolis St Paul
Delta Logo
10:12 am - 2:42 pmMDW  Chicago Midway-MCI Kansas City
4h 30m1 stop Minneapolis St Paul
$277Delta
Sat, Oct 17 - Tue, Oct 20
Delta Logo
6:20 am - 1:20 pmMCI  Kansas City-MDW Chicago Midway
7h 00m1 stop Minneapolis St Paul
Delta Logo
9:59 am - 3:09 pmMDW  Chicago Midway-MCI Kansas City
5h 10m1 stop Minneapolis St Paul
$277Delta
Thu, Sep 24 - Sat, Sep 26

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Frontier flights from Kansas City to Chicago Midway Airport

Our best Frontier deals on Kansas City to Chicago Midway Airport flight tickets
Frontier
Sep 2
MCI11:26 amKansas City
11h 21m
1 stop
MDW10:47 pmChicago Midway
Sep 5
MDW6:05 amChicago Midway
10h 00m
1 stop
MCI4:05 pmKansas City
$310
Frontier
Sep 2
MCI11:26 amKansas City
11h 21m
1 stop
MDW10:47 pmChicago Midway
Sep 5
MDW6:05 amChicago Midway
10h 00m
1 stop
MCI4:05 pmKansas City
$320
Frontier
Sep 2
MCI11:26 amKansas City
11h 21m
1 stop
MDW10:47 pmChicago Midway
Sep 5
MDW6:05 amChicago Midway
10h 00m
1 stop
MCI4:05 pmKansas City
$324

Southwest flights from Kansas City to Chicago Midway Airport

Our best Southwest deals on Kansas City to Chicago Midway Airport flight tickets
Southwest
Oct 10
MCI4:05 pmKansas City
1h 25m
MDW5:30 pmChicago Midway
Oct 12
MDW9:30 pmChicago Midway
1h 35m
MCI11:05 pmKansas City
$257
Southwest
Oct 21
MCI1:55 pmKansas City
2h 55m
1 stop
MDW4:50 pmChicago Midway
Oct 26
MDW6:25 pmChicago Midway
1h 30m
MCI7:55 pmKansas City
$263
Southwest
Oct 10
MCI2:55 pmKansas City
2h 50m
1 stop
MDW5:45 pmChicago Midway
Oct 12
MDW9:30 pmChicago Midway
1h 35m
MCI11:05 pmKansas City
$267

momondo Fare Finder

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

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Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Wed 9/23

3:35 pm-5:00 pm

Nonstop1h 25m

Chicago Midway

Sat 9/26

12:00 pm-1:25 pm

Nonstop1h 25m

$257

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Mon 10/5

5:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Thu 10/8

2:25 pm-3:50 pm

Nonstop1h 25m

$257

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Mon 10/19

5:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Wed 10/21

7:50 am-9:20 am

Nonstop1h 30m

$257

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Tue 11/17

8:00 am-9:25 am

Nonstop1h 25m

Chicago Midway

Thu 11/19

10:05 am-11:35 am

Nonstop1h 30m

$257

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Wed 9/30

5:55 pm-7:20 pm

Nonstop1h 25m

Chicago Midway

Wed 10/7

6:00 am-7:30 am

Nonstop1h 30m

$257

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Thu 9/24

8:10 pm-9:35 pm

Nonstop1h 25m

Chicago Midway

Mon 9/28

7:30 am-8:55 am

Nonstop1h 25m

$257

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Thu 10/1

5:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Mon 10/5

9:30 pm-11:05 pm

Nonstop1h 35m

$257

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Tue 9/29

5:55 pm-7:20 pm

Nonstop1h 25m

Chicago Midway

Tue 10/6

12:05 pm-1:30 pm

Nonstop1h 25m

$257

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Sat 10/17

6:30 am-11:47 am

1 stop5h 17m

Chicago Midway

Tue 10/20

10:12 am-2:42 pm

1 stop4h 30m

$277

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Thu 9/24

6:20 am-1:20 pm

1 stop7h 00m

Chicago Midway

Sat 9/26

9:59 am-3:09 pm

1 stop5h 10m

$277

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Kansas City to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Kansas City and Chicago Midway Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $287 to $571.
The lowest price recently found on this route was $257.

What is the cheapest month to fly to Chicago Midway Airport?

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Kansas City, with most prices found around $329. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Kansas City during the month November is also very affordable. Most momondo users find prices during this month for around $340.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Kansas City. The lowest ticket price found for a Saturday departure recently was $394. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Kansas City because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $517.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Kansas City in the evening is the least expensive time of day to depart. momondo users have found prices as low as $373 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $457. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Kansas City to Chicago Midway flight route?

Fly from Kansas City to Chicago Midway for the best Kansas City - Chicago Midway flight prices

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

You are more likely to see cheaper flights to Chicago Midway Airport from Kansas City when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $430 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Kansas City for as low as $315 on momondo.

What cabin class options are available on Kansas City to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Kansas City to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Kansas City to Chicago Midway Airport flights?

You could potentially save up to 2% on your flight if you consider stops on a Kansas City to Chicago Midway Airport flight.

How have Kansas City to Chicago Midway Airport flight prices changed over time?

As of September 2026, prices for Kansas City to Chicago Midway Airport flights are approximately 59% cheaper when compared to flights at the same time last year.

When to book flights from Kansas City to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Kansas City to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Kansas City to Chicago Midway Airport (MCI to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Kansas City to Chicago Midway Airport

Best Price Found

$129

Fastest flight time

1h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Kansas City in the past 72 hours is $129. The best round-trip flight deal from Kansas City to Chicago Midway Airport found on momondo in the last 72 hours is $257.
The fastest flight from Kansas City to Chicago Midway Airport takes 1h 20m
Direct flights go from Kansas City to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Kansas City to Chicago Midway Airport

  • How far is Kansas City to Chicago Midway by plane?

    The straight-line distance from Kansas City to Chicago Midway is 404.6 mi. Typically, this will take 1h 20m by plane in normal conditions.

  • When did momondo last update prices for flights from Kansas City Airport to Chicago Midway Airport?

    Prices for flights from Kansas City Airport to Chicago Midway Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Kansas City Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Kansas City Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Kansas City Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Kansas City to Chicago Midway Airport?

  • What is the most popular airline from Kansas City to Chicago Midway Airport?

Best airlines flying from Kansas City to Chicago Midway Airport

Compare and see reviews for airlines that fly from Kansas City to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $245Free CancellationRating
8.0
4,192 reviews
Search Southwest flights

  • Southwest Flights From Kansas City to Chicago Midway Airport

    The lowest priced Southwest flight from Kansas City to Chicago Midway Airport from the last 72 hours was $245. Generally, Southwest has 15 flights on this route every week with an average price of $450. Southwest is rated 8.0/10 by our users.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Kansas City to Chicago?

It is quick and easy to find Kansas City to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Kansas City to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Kansas City to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Kansas City to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Kansas City to Chicago.

I’m not ready to book a flight from Kansas City to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Kansas City are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport trip

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