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Cheap flights from Kansas City to Chicago from $140

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Kansas City to Chicago departing on 7/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Kansas City to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
2:05 pm - 5:00 pm
MCI
-
MDW
2h 55m
1 stop
Southwest Logo
7:40 am - 1:30 pm
MDW
-
MCI
5h 50m
2 stops
$326Southwest
Tue, Jul 28 - Tue, Aug 4
Southwest Logo
8:10 am - 9:35 am
MCI
-
MDW
1h 25mnonstop
Southwest Logo
6:30 am - 7:55 am
MDW
-
MCI
1h 25mnonstop
$327Southwest
Wed, Jul 15 - Sun, Jul 19
Southwest Logo
2:05 pm - 5:00 pm
MCI
-
MDW
2h 55m
1 stop
Southwest Logo
10:10 am - 4:15 pm
MDW
-
MCI
6h 05m
2 stops
$328Southwest
Tue, Jun 23 - Tue, Jun 30
Southwest Logo
5:05 am - 6:35 am
MCI
-
MDW
1h 30mnonstop
Southwest Logo
8:00 am - 9:30 am
MDW
-
MCI
1h 30mnonstop
$329Southwest
Sat, Jun 27 - Mon, Jun 29
Southwest Logo
10:40 am - 5:00 pm
MCI
-
MDW
6h 20m
2 stops
Southwest Logo
2:35 pm - 5:25 pm
MDW
-
MCI
2h 50m
1 stop
$330Southwest
Sat, Jun 20 - Sat, Jun 27
Southwest Logo
7:45 am - 1:35 pm
MCI
-
MDW
5h 50m
2 stops
Southwest Logo
10:10 am - 1:35 pm
MDW
-
MCI
3h 25m
1 stop
$332Southwest
Tue, Jul 7 - Wed, Jul 15
Southwest Logo
2:05 pm - 5:00 pm
MCI
-
MDW
2h 55m
1 stop
Southwest Logo
6:30 am - 7:55 am
MDW
-
MCI
1h 25mnonstop
$333Southwest
Wed, Jul 15 - Sun, Jul 19
Southwest Logo
3:45 pm - 5:10 pm
MCI
-
MDW
1h 25mnonstop
Southwest Logo
11:00 am - 5:25 pm
MDW
-
MCI
6h 25m
2 stops
$334Southwest
Thu, Aug 20 - Mon, Aug 24
Delta Logo
6:23 am - 1:09 pm
MCI
-
MDW
6h 46m
1 stop
Delta Logo
9:49 am - 3:14 pm
MDW
-
MCI
5h 25m
1 stop
$337Delta
Tue, Jul 14 - Fri, Jul 17
Southwest Logo
7:45 am - 1:35 pm
MCI
-
MDW
5h 50m
2 stops
Southwest Logo
10:20 am - 1:10 pm
MDW
-
MCI
2h 50m
1 stop
$338Southwest
Tue, Jul 7 - Thu, Jul 9

Delta flights from Kansas City to Chicago Midway Airport

Our best Delta deals on Kansas City to Chicago Midway Airport flight tickets
Delta
Jul 14
MCI6:23 amKansas City
6h 46m
1 stop
MDW1:09 pmChicago Midway
Jul 17
MDW9:49 amChicago Midway
5h 25m
1 stop
MCI3:14 pmKansas City
$337
Delta
Jun 20
MCI12:30 pmKansas City
5h 24m
1 stop
MDW5:54 pmChicago Midway
Jun 24
MDW9:54 amChicago Midway
5h 20m
1 stop
MCI3:14 pmKansas City
$347
Delta
Jun 13
MCI12:30 pmKansas City
5h 24m
1 stop
MDW5:54 pmChicago Midway
Jun 17
MDW9:54 amChicago Midway
5h 30m
1 stop
MCI3:24 pmKansas City
$357

Southwest flights from Kansas City to Chicago Midway Airport

Our best Southwest deals on Kansas City to Chicago Midway Airport flight tickets
Southwest
Jul 28
MCI2:05 pmKansas City
2h 55m
1 stop
MDW5:00 pmChicago Midway
Aug 4
MDW7:40 amChicago Midway
5h 50m
2 stops
MCI1:30 pmKansas City
$326
Southwest
Jul 15
MCI4:50 pmKansas City
1h 25m
MDW6:15 pmChicago Midway
Jul 19
MDW6:30 amChicago Midway
1h 25m
MCI7:55 amKansas City
$327
Southwest
Jun 23
MCI2:05 pmKansas City
2h 55m
1 stop
MDW5:00 pmChicago Midway
Jun 30
MDW10:10 amChicago Midway
6h 05m
2 stops
MCI4:15 pmKansas City
$328

momondo Fare Finder

 
Customize your flight search to find flights from Kansas City to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated May 26, 2026.
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 - MDW

MCIMDW

Kansas City

Tue 7/28

2:05 pm-5:00 pm

1 stop2h 55m

Chicago Midway

Tue 8/4

7:40 am-1:30 pm

2 stops5h 50m

$326
Quickest round-trip

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Wed 7/15

8:10 am-9:35 am

Nonstop1h 25m

Chicago Midway

Sun 7/19

6:30 am-7:55 am

Nonstop1h 25m

$327

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Tue 6/23

2:05 pm-5:00 pm

1 stop2h 55m

Chicago Midway

Tue 6/30

10:10 am-4:15 pm

2 stops6h 05m

$328

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Sat 6/27

5:05 am-6:35 am

Nonstop1h 30m

Chicago Midway

Mon 6/29

8:00 am-9:30 am

Nonstop1h 30m

$329

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Sat 6/20

10:40 am-5:00 pm

2 stops6h 20m

Chicago Midway

Sat 6/27

2:35 pm-5:25 pm

1 stop2h 50m

$330

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Tue 7/7

7:45 am-1:35 pm

2 stops5h 50m

Chicago Midway

Wed 7/15

10:10 am-1:35 pm

1 stop3h 25m

$332

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Wed 7/15

2:05 pm-5:00 pm

1 stop2h 55m

Chicago Midway

Sun 7/19

6:30 am-7:55 am

Nonstop1h 25m

$333

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Thu 8/20

3:45 pm-5:10 pm

Nonstop1h 25m

Chicago Midway

Mon 8/24

11:00 am-5:25 pm

2 stops6h 25m

$334

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Tue 7/14

6:23 am-1:09 pm

1 stop6h 46m

Chicago Midway

Fri 7/17

9:49 am-3:14 pm

1 stop5h 25m

$337

Kansas CityChicago

MCI - MDW

MCIMDW

Kansas City

Tue 7/7

7:45 am-1:35 pm

2 stops5h 50m

Chicago Midway

Thu 7/9

10:20 am-1:10 pm

1 stop2h 50m

$338

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?

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

The month of November is, on average, the cheapest month to fly to Chicago Midway Airport from Kansas City, with most prices found around $299. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Kansas City during the month August is also very affordable. Most momondo users find prices during this month for around $299.

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 $369. 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 $483.

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 $352 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $441. 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 $408 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 $254 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 7% 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 May 2026, prices for Kansas City to Chicago Midway Airport flights are approximately 38% 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

$203

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 $203. The best round-trip flight deal from Kansas City to Chicago Midway Airport found on momondo in the last 72 hours is $379.
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 $229Free CancellationRating
8.0
4,266 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 $229. Generally, Southwest has 32 flights on this route every week with an average price of $425. Southwest is rated 8.0/10 by our users.

Traveling to a place near Chicago?

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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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