What is the cheapest airline that flies from Chicago Midway to Kentucky?

Frontier, Southwest, and Delta are the most popular carriers operating from Chicago Midway to Kentucky

How many flights depart from Chicago Midway Airport to Kentucky on average per week?

22 flights are operational weekly from Chicago Midway Airport to Kentucky as of April 2026. The most popular departure day for this route is Mon, with 50% of flights per week taking off on this day.

How many flights depart from Chicago Midway Airport to Kentucky on average per day?

As of April 2026, there are 3 flights per day flying from Chicago Midway Airport to Kentucky. The most common time of day flights depart is 7:00AM, with 37% of flights taking off at noon.

When did momondo last update prices for flights from Chicago Midway Airport to Kentucky?

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

How many operators does momondo search for flights from Chicago Midway Airport to Kentucky?

As of April 2026, there are 3 operators available to choose from for flights from Chicago Midway Airport to Kentucky.

How old do you have to be to fly from Chicago Midway Airport to Kentucky?

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 Chicago Midway Airport to Kentucky.

What documentation or ID do you need to fly to Kentucky?

The travel and health documents required for your trip to Kentucky can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Kentucky. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$68 Cheap Flights from Chicago Midway Airport to Kentucky in 2026

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Find the cheapest flights from Chicago Midway Airport to Kentucky

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:48 pm - 5:18 pm

MDW

TYS

1h 30mnonstop

9:00 am - 8:18 am

TYS

MDW

24h 18m

1 stop

$204Allegiant Air

Thu, Jul 2 - Sat, Jul 4

2:46 pm - 5:14 pm

MDW

TYS

1h 28mnonstop

1:22 pm - 1:56 pm

TYS

MDW

1h 34mnonstop

$206Allegiant Air

Sun, Jun 14 - Thu, Jun 18

8:26 am - 11:20 pm

MDW

CVG

13h 54m

1 stop

5:20 pm - 8:04 am

CVG

MDW

15h 44m

1 stop

$212Frontier

Thu, Apr 23 - Sun, Apr 26

2:48 pm - 5:18 pm

MDW

TYS

1h 30mnonstop

10:05 pm - 10:11 pm

TYS

MDW

25h 06m

2 stops

$214Multiple Airlines

Thu, Jul 2 - Fri, Jul 3

5:30 am - 11:50 am

MDW

CVG

5h 20m

1 stop

5:45 am - 1:10 pm

CVG

MDW

8h 25m

2 stops

$216Southwest

Thu, Apr 23 - Mon, Apr 27

9:14 am - 4:58 pm

MDW

BNA

7h 44m

1 stop

9:30 am - 10:14 pm

BNA

MDW

12h 44m

2 stops

$217Multiple Airlines

Sat, Apr 25 - Tue, Apr 28

9:14 am - 4:58 pm

MDW

BNA

7h 44m

1 stop

8:48 pm - 10:14 pm

BNA

MDW

25h 26m

2 stops

$218Frontier

Sat, Apr 25 - Mon, Apr 27

6:10 pm - 8:20 pm

MDW

CVG

1h 10mnonstop

7:35 pm - 7:50 pm

CVG

MDW

1h 15mnonstop

$227Southwest

Tue, May 5 - Wed, May 6

6:23 am - 12:56 pm

MDW

TRI

5h 33m

1 stop

4:49 pm - 9:09 pm

TRI

MDW

5h 20m

1 stop

$249Delta

Sat, May 16 - Sat, May 23

6:00 am - 1:03 pm

MDW

TRI

6h 03m

1 stop

5:08 pm - 10:28 pm

TRI

MDW

6h 20m

1 stop

$264Delta

Wed, Apr 22 - Sat, Apr 25

Southwest flights from Chicago Midway Airport to Kentucky

Our best Southwest deals on Chicago Midway Airport to Kentucky flight tickets

Southwest

Apr 23

MDW5:30 amChicago Midway

5h 20m

1 stop

CVG11:50 amCincinnati Cinci./N. Kentucky

Apr 27

CVG5:45 amCincinnati Cinci./N. Kentucky

8h 25m

2 stops

MDW1:10 pmChicago Midway

$216

Southwest

May 5

MDW6:10 pmChicago Midway

1h 10m

CVG8:20 pmCincinnati Cinci./N. Kentucky

May 6

CVG7:35 pmCincinnati Cinci./N. Kentucky

1h 15m

MDW7:50 pmChicago Midway

$227

Southwest

May 12

MDW6:10 pmChicago Midway

1h 10m

CVG8:20 pmCincinnati Cinci./N. Kentucky

May 15

CVG9:00 amCincinnati Cinci./N. Kentucky

1h 15m

MDW9:15 amChicago Midway

$229

Frontier flights from Chicago Midway Airport to Kentucky

Our best Frontier deals on Chicago Midway Airport to Kentucky flight tickets

Frontier

Apr 23

MDW8:26 amChicago Midway

13h 54m

1 stop

CVG11:20 pmCincinnati Cinci./N. Kentucky

Apr 26

CVG5:20 pmCincinnati Cinci./N. Kentucky

15h 44m

1 stop

MDW8:04 amChicago Midway

$212

Frontier

Apr 25

MDW9:14 amChicago Midway

7h 44m

1 stop

BNA4:58 pmNashville Intl

Apr 27

BNA8:48 pmNashville Intl

25h 26m

2 stops

MDW10:14 pmChicago Midway

$218

Frontier

Apr 17

MDW9:14 amChicago Midway

13h 06m

1 stop

CVG11:20 pmCincinnati Cinci./N. Kentucky

Apr 20

CVG1:05 pmCincinnati Cinci./N. Kentucky

10h 16m

1 stop

MDW10:21 pmChicago Midway

$222

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Thu 7/2

2:48 pm-5:18 pm

Nonstop1h 30m

Knoxville McGhee Tyson

Sat 7/4

9:00 am-8:18 am

1 stop24h 18m

$204

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Sun 6/14

2:46 pm-5:14 pm

Nonstop1h 28m

Knoxville McGhee Tyson

Thu 6/18

1:22 pm-1:56 pm

Nonstop1h 34m

$206

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 4/23

8:26 am-11:20 pm

1 stop13h 54m

Cincinnati Cinci./N. Kentucky

Sun 4/26

5:20 pm-8:04 am

1 stop15h 44m

$212

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Thu 7/2

2:48 pm-5:18 pm

Nonstop1h 30m

Knoxville McGhee Tyson

Fri 7/3

10:05 pm-10:11 pm

2 stops25h 06m

$214

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 4/23

5:30 am-11:50 am

1 stop5h 20m

Cincinnati Cinci./N. Kentucky

Mon 4/27

5:45 am-1:10 pm

2 stops8h 25m

$216

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sat 4/25

9:14 am-4:58 pm

1 stop7h 44m

Nashville Intl

Tue 4/28

9:30 am-10:14 pm

2 stops12h 44m

$217

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sat 4/25

9:14 am-4:58 pm

1 stop7h 44m

Nashville Intl

Mon 4/27

8:48 pm-10:14 pm

2 stops25h 26m

$218

Quickest round-trip

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Tue 5/5

6:10 pm-8:20 pm

Nonstop1h 10m

Cincinnati Cinci./N. Kentucky

Wed 5/6

7:35 pm-7:50 pm

Nonstop1h 15m

$227

ChicagoBlountville

MDW - TRI

MDWTRI

Chicago Midway

Sat 5/16

6:23 am-12:56 pm

1 stop5h 33m

Blountville Tri Cities TN/VA

Sat 5/23

4:49 pm-9:09 pm

1 stop5h 20m

$249

ChicagoBlountville

MDW - TRI

MDWTRI

Chicago Midway

Wed 4/22

6:00 am-1:03 pm

1 stop6h 03m

Blountville Tri Cities TN/VA

Sat 4/25

5:08 pm-10:28 pm

1 stop6h 20m

$264

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Kentucky

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

Prices

Airlines

Other information

What is the cheapest day to depart on your flight to Kentucky?

Our data shows that Thursday is the least expensive day to fly to Kentucky. Tickets to fly out on this day can be as low as $237. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $558. These prices are subject to change though, so be sure to set up a Price Alert for flights to Kentucky.

What is the cheapest time of day to depart on your flight to Kentucky?

According to our data, the cheapest time of day to fly to Kentucky is in the afternoon. momondo users have found flights departing from Chicago Midway Airport to Kentucky in the afternoon for as low as $255. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Kentucky is in the evening when prices are around $351.

What is the cheapest Chicago Midway to Kentucky flight route?

Fly from Chicago Midway to Louisville Intl for the best Chicago Midway - Kentucky flight prices

What cabin class options are available on Chicago Midway to Kentucky flights?

There is only 1 cabin class available to choose from on Chicago Midway to Kentucky 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 Chicago Midway Airport to Kentucky flights?

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

Cheap Chicago Midway Airport to Kentucky flight deals and tips

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

Best Price Found	$222
Fastest flight time	1h 10m
Direct flights	Every day
Airports in Kentucky	43 airports

The best one-way flight to Kentucky from Chicago Midway Airport in the past 72 hours is $222. The best round-trip flight deal from Chicago Midway Airport to Kentucky found on momondo in the last 72 hours is $306.

The fastest flight from Chicago Midway Airport to Kentucky takes 1h 10m

Direct flights go from Chicago Midway Airport to Kentucky every day.

There are 43 airports in Kentucky. From Chicago Midway Airport there are direct flights to Louisville Intl (SDF), Nashville Intl (BNA), Cincinnati Cinci./N. Kentucky (CVG).

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Kentucky

When did momondo last update prices for flights from Chicago Midway Airport to Kentucky?
Prices for flights from Chicago Midway Airport to Kentucky are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Kentucky?
As of April 2026, there are 3 operators available to choose from for flights from Chicago Midway Airport to Kentucky.
How old do you have to be to fly from Chicago Midway Airport to Kentucky?
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 Chicago Midway Airport to Kentucky.
What documentation or ID do you need to fly to Kentucky?
The travel and health documents required for your trip to Kentucky can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Kentucky. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago Midway Airport to Kentucky?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Kentucky is Boeing 737-800 Passenger/BBJ2 (winglets), representing 15.83% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 12.95%, Embraer 175 at 12.95%, and Embraer 175 (Enhanced Winglets) at 11.51%.

Best airlines flying from Chicago Midway Airport to Kentucky

Compare and see reviews for airlines that fly from Chicago Midway Airport to Kentucky with momondo

Airline	Rating	Free Cancellation	Price
Southwest	PriceFrom $124	Free Cancellation	Rating 8.0 4,338 reviews		Search Southwest flights

Why use momondo?

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

It is quick and easy to find Chicago to Kentucky 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 Kentucky that suits you.

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

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

How can momondo help me find flights from Chicago to Kentucky?

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 Chicago to Kentucky.

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

Price alerts on flights to Kentucky from Chicago 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.