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Not ready to book? to track prices.Southwest flights from Kansas City to Chicago Midway Airport
Our best Southwest deals on Kansas City to Chicago Midway Airport flight tickets
Frontier flights from Kansas City to Chicago Midway Airport
Our best Frontier deals on Kansas City to Chicago Midway Airport flight tickets
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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
Kansas CityChicago
MCI Kansas City - MDW Chicago Midway
MCIMDW
Kansas City
Thu 11/5
8:35 pm-10:00 pm
Nonstop1h 25m
Chicago Midway
Mon 11/9
10:55 pm-12:35 am
Nonstop1h 40m
Kansas CityChicago
MCI Kansas City - MDW Chicago Midway
MCIMDW
Kansas City
Thu 10/22
8:40 pm-10:00 pm
Nonstop1h 20m
Chicago Midway
Sat 10/24
8:05 am-2:50 pm
2 stops6h 45m
Kansas CityChicago
MCI Kansas City - MDW Chicago Midway
MCIMDW
Kansas City
Tue 10/27
1:55 pm-4:50 pm
1 stop2h 55m
Chicago Midway
Thu 10/29
8:35 am-1:25 pm
1 stop4h 50m
Kansas CityChicago
MCI Kansas City - MDW Chicago Midway
MCIMDW
Kansas City
Sat 11/14
6:10 am-2:30 pm
2 stops8h 20m
Chicago Midway
Sat 11/21
7:00 am-8:40 am
Nonstop1h 40m
Kansas CityChicago
MCI Kansas City - MDW Chicago Midway
MCIMDW
Kansas City
Tue 10/27
12:33 pm-4:47 pm
1 stop4h 14m
Chicago Midway
Thu 10/29
10:12 am-2:42 pm
1 stop4h 30m
Kansas CityChicago
MCI Kansas City - MDW Chicago Midway
MCIMDW
Kansas City
Sat 11/7
6:10 am-2:30 pm
2 stops8h 20m
Chicago Midway
Mon 11/9
10:55 pm-12:35 am
Nonstop1h 40m
Kansas CityChicago
MCI Kansas City - MDW Chicago Midway
MCIMDW
Kansas City
Sat 10/31
9:20 am-3:25 pm
1 stop6h 05m
Chicago Midway
Mon 11/2
6:50 am-8:30 am
Nonstop1h 40m
Kansas CityChicago
MCI Kansas City - MDW Chicago Midway
MCIMDW
Kansas City
Wed 11/18
6:00 am-11:50 am
1 stop5h 50m
Chicago Midway
Wed 11/18
5:29 pm-11:24 pm
1 stop5h 55m
Kansas CityChicago
MCI Kansas City - MDW Chicago Midway
MCIMDW
Kansas City
Thu 10/29
6:00 pm-11:55 pm
1 stop5h 55m
Chicago Midway
Thu 11/5
5:55 am-12:25 pm
1 stop6h 30m
Kansas CityChicago
MCI Kansas City - MDW Chicago Midway
MCIMDW
Kansas City
Wed 12/2
6:50 am-12:15 pm
1 stop5h 25m
Chicago Midway
Mon 12/7
12:45 pm-4:35 pm
1 stop3h 50m
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 $305 to $444.The lowest price recently found on this route was $252.
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 December is also very affordable. Most momondo users find prices during this month for around $349.
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 $442 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?
You could potentially save up to 15% 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 October 2026, prices for Kansas City to Chicago Midway Airport flights are approximately 28% more expensive when compared to flights at the same time last year.
How many flights depart from Kansas City to Chicago Midway Airport on average per day?
As of October 2026, there are 3 flights per day flying from Kansas City to Chicago Midway Airport. The most common time of day flights depart is 5:00AM, with 31% of flights taking off at noon.
How many flights depart from Kansas City to Chicago Midway Airport on average per week?
The number of flights available between Kansas City and Chicago Midway Airport is 21 per week as of October 2026. The most frequent departure day is Mon, with 33% of weekly flights leaving on this day.
When to book flights from Kansas City to Chicago Midway Airport
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
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?
The number of operators available for flights from Kansas City Airport to Chicago Midway Airport is 1 as of October 2026.
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?
momondo data reveals that the most frequently booked plane model on the route from Kansas City to Chicago Midway Airport is Boeing 737 MAX 8, representing 13.71% of all bookings. The subsequent popular models are Airbus A319 at 11.93%, Boeing 737-800 at 11.84%, and Embraer 175 (Enhanced Winglets) at 11.41%.
What is the most popular airline from Kansas City to Chicago Midway Airport?
momondo data reveals that the most frequently booked airline on the route from Kansas City to Chicago Midway Airport is Southwest, representing 100% of all bookings.
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 | ||
|---|---|---|---|---|---|
| PriceFrom $257 | Free Cancellation | Rating 7.9 4,214 reviews |
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 21 flights on this route every week with an average price of $456. Southwest is rated 7.9/10 by our users.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy 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.