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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
6:25 pm - 7:50 pmMCI  Kansas City-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
5:20 pm - 6:50 pmMDW  Chicago Midway-MCI Kansas City
1h 30mnonstop
$237Southwest
Wed, Dec 2 - Mon, Dec 7
Southwest Logo
3:50 pm - 5:10 pmMCI  Kansas City-MDW Chicago Midway
1h 20mnonstop
Southwest Logo
3:45 pm - 5:15 pmMDW  Chicago Midway-MCI Kansas City
1h 30mnonstop
$237Southwest
Fri, Dec 4 - Wed, Dec 9
Southwest Logo
5:10 am - 6:35 amMCI  Kansas City-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
7:45 pm - 9:20 pmMDW  Chicago Midway-MCI Kansas City
1h 35mnonstop
$237Southwest
Wed, Dec 30 - Thu, Jan 7
Southwest Logo
2:40 pm - 4:10 pmMCI  Kansas City-MDW Chicago Midway
1h 30mnonstop
Southwest Logo
11:45 am - 1:15 pmMDW  Chicago Midway-MCI Kansas City
1h 30mnonstop
$237Southwest
Thu, Dec 3 - Thu, Dec 10
Southwest Logo
5:10 am - 6:35 amMCI  Kansas City-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
8:10 am - 9:50 amMDW  Chicago Midway-MCI Kansas City
1h 40mnonstop
$237Southwest
Wed, Dec 30 - Tue, Jan 5
Southwest Logo
5:35 am - 7:00 amMCI  Kansas City-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
10:55 pm - 12:35 amMDW  Chicago Midway-MCI Kansas City
1h 40mnonstop
$237Southwest
Fri, Nov 27 - Fri, Nov 27
Southwest Logo
3:50 pm - 5:10 pmMCI  Kansas City-MDW Chicago Midway
1h 20mnonstop
Southwest Logo
9:40 pm - 11:15 pmMDW  Chicago Midway-MCI Kansas City
1h 35mnonstop
$237Southwest
Wed, Dec 16 - Fri, Dec 18
Southwest Logo
5:15 am - 6:45 amMCI  Kansas City-MDW Chicago Midway
1h 30mnonstop
Southwest Logo
9:50 am - 11:25 amMDW  Chicago Midway-MCI Kansas City
1h 35mnonstop
$237Southwest
Fri, Feb 5 - Thu, Feb 11
Frontier Logo
8:15 am - 7:42 pmMCI  Kansas City-MDW Chicago Midway
11h 27m1 stop Orlando
Frontier Logo
8:47 pm - 7:20 amMDW  Chicago Midway-MCI Kansas City
10h 33m1 stop Orlando
$238Frontier
Fri, Jan 29 - Sun, Jan 31
Frontier Logo
10:30 am - 5:16 pmMCI  Kansas City-MDW Chicago Midway
6h 46m1 stop Orlando
Frontier Logo
8:37 pm - 9:35 amMDW  Chicago Midway-MCI Kansas City
12h 58m1 stop Orlando
$238Frontier
Fri, Dec 11 - Sun, Dec 13

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Southwest flights from Kansas City to Chicago Midway Airport

Our best Southwest deals on Kansas City to Chicago Midway Airport flight tickets
Southwest
Dec 30
MCI5:10 amKansas City
1h 25m
MDW6:35 amChicago Midway
Jan 5
MDW8:10 amChicago Midway
1h 40m
MCI9:50 amKansas City
$237
Southwest
Dec 30
MCI6:05 pmKansas City
4h 55m
1 stop
MDW11:00 pmChicago Midway
Jan 6
MDW8:35 amChicago Midway
1h 40m
MCI10:15 amKansas City
$247
Southwest
Dec 30
MCI9:55 pmKansas City
1h 30m
MDW11:25 pmChicago Midway
Jan 5
MDW3:45 pmChicago Midway
6h 25m
2 stops
MCI10:10 pmKansas City
$252

Frontier flights from Kansas City to Chicago Midway Airport

Our best Frontier deals on Kansas City to Chicago Midway Airport flight tickets
Frontier
Dec 11
MCI10:30 amKansas City
6h 46m
1 stop
MDW5:16 pmChicago Midway
Dec 13
MDW8:37 pmChicago Midway
12h 58m
1 stop
MCI9:35 amKansas City
$238
Frontier
Nov 23
MCI11:11 amKansas City
8h 36m
1 stop
MDW7:47 pmChicago Midway
Dec 3
MDW3:36 pmChicago Midway
17h 58m
1 stop
MCI9:34 amKansas City
$249
Frontier
Jan 22
MCI8:15 amKansas City
11h 27m
1 stop
MDW7:42 pmChicago Midway
Jan 24
MDW8:47 pmChicago Midway
10h 33m
1 stop
MCI7:20 amKansas City
$254

momondo 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

Wed 12/2

6:25 pm-7:50 pm

Nonstop1h 25m

Chicago Midway

Mon 12/7

5:20 pm-6:50 pm

Nonstop1h 30m

$237
Quickest round-trip

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Fri 12/4

3:50 pm-5:10 pm

Nonstop1h 20m

Chicago Midway

Wed 12/9

3:45 pm-5:15 pm

Nonstop1h 30m

$237

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Wed 12/30

5:10 am-6:35 am

Nonstop1h 25m

Chicago Midway

Thu 1/7

7:45 pm-9:20 pm

Nonstop1h 35m

$237

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Thu 12/3

2:40 pm-4:10 pm

Nonstop1h 30m

Chicago Midway

Thu 12/10

11:45 am-1:15 pm

Nonstop1h 30m

$237

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Wed 12/30

5:10 am-6:35 am

Nonstop1h 25m

Chicago Midway

Tue 1/5

8:10 am-9:50 am

Nonstop1h 40m

$237

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Fri 11/27

5:35 am-7:00 am

Nonstop1h 25m

Chicago Midway

Fri 11/27

10:55 pm-12:35 am

Nonstop1h 40m

$237

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Wed 12/16

3:50 pm-5:10 pm

Nonstop1h 20m

Chicago Midway

Fri 12/18

9:40 pm-11:15 pm

Nonstop1h 35m

$237

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Fri 2/5

5:15 am-6:45 am

Nonstop1h 30m

Chicago Midway

Thu 2/11

9:50 am-11:25 am

Nonstop1h 35m

$237

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Fri 1/29

8:15 am-7:42 pm

1 stop11h 27m

Chicago Midway

Sun 1/31

8:47 pm-7:20 am

1 stop10h 33m

$238

Kansas CityChicago

MCI Kansas City - MDW Chicago Midway

MCIMDW

Kansas City

Fri 12/11

10:30 am-5:16 pm

1 stop6h 46m

Chicago Midway

Sun 12/13

8:37 pm-9:35 am

1 stop12h 58m

$238

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 $359 to $481.
The lowest price recently found on this route was $237.

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 $399.

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 $458 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 $320 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?

No. A direct flight is the cheapest option for a flight between Kansas City to Chicago Midway Airport.

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

As of November 2026, prices for Kansas City to Chicago Midway Airport flights are approximately 118% more expensive 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 $237.
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 $257Free CancellationRating
8.0
4,214 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 $257. Generally, Southwest has 40 flights on this route every week with an average price of $462. 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
Lansing
Saint Joseph
Benton Harbor
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
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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