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

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

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

As of July 2026, there are 6 flights per day flying from Chicago Midway Airport to Kentucky. The most common time of day flights depart is 7:00AM, with 44% of flights taking off at noon.

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

47 flights are operational weekly from Chicago Midway Airport to Kentucky as of July 2026. The most popular departure day for this route is Sun, with 30% of flights per week taking off on this day.

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 July 2026, there are 2 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.

$51 Cheap Flights from Chicago Midway Airport to Kentucky in 2026

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.

2:49 pm - 5:19 pm

MDW

TYS

1h 30mnonstop

1:23 pm - 1:59 pm

TYS

MDW

1h 36mnonstop

$155Allegiant Air

Sun, Aug 9 - Thu, Aug 13

3:25 pm - 5:35 pm

MDW

CVG

1h 10mnonstop

8:20 am - 8:25 am

CVG

MDW

1h 05mnonstop

$157Southwest

Sat, Aug 15 - Sat, Aug 22

2:48 pm - 5:18 pm

MDW

TYS

1h 30mnonstop

1:23 pm - 1:59 pm

TYS

MDW

1h 36mnonstop

$159Allegiant Air

Thu, Jul 30 - Thu, Aug 6

2:25 pm - 6:50 pm

MDW

CVG

3h 25m

1 stop

8:20 am - 8:25 am

CVG

MDW

1h 05mnonstop

$167Southwest

Sat, Aug 15 - Sat, Aug 22

8:00 am - 10:25 am

MDW

CVG

1h 25mnonstop

6:40 am - 1:20 pm

CVG

MDW

7h 40m

2 stops

$172Southwest

Sat, Aug 15 - Sat, Aug 22

8:00 am - 10:25 am

MDW

CVG

1h 25mnonstop

8:10 am - 8:15 am

CVG

MDW

1h 05mnonstop

$176Southwest

Sat, Aug 8 - Mon, Aug 10

9:24 am - 4:41 pm

MDW

SDF

6h 17m

1 stop

2:34 pm - 6:33 pm

SDF

MDW

4h 59m

1 stop

$255Delta

Sat, Aug 8 - Mon, Aug 10

6:00 am - 10:09 am

MDW

BNA

4h 09m

1 stop

10:59 am - 3:38 pm

BNA

MDW

4h 39m

1 stop

$257Delta

Sat, Aug 1 - Sat, Aug 8

9:26 pm - 9:01 am

MDW

BNA

11h 35m

1 stop

9:56 am - 8:31 pm

BNA

MDW

10h 35m

1 stop

$258Frontier

Thu, Aug 27 - Mon, Aug 31

9:26 pm - 9:01 am

MDW

BNA

11h 35m

1 stop

9:56 am - 8:31 pm

BNA

MDW

10h 35m

1 stop

$260Frontier

Thu, Aug 20 - Thu, Aug 27

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Delta flights from Chicago Midway Airport to Kentucky

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

Delta

Aug 4

MDW9:24 amChicago Midway

3h 18m

1 stop

CVG1:42 pmCincinnati Cinci./N. Kentucky

Aug 6

CVG4:10 pmCincinnati Cinci./N. Kentucky

3h 23m

1 stop

MDW6:33 pmChicago Midway

$237

Delta

Aug 8

MDW9:24 amChicago Midway

6h 17m

1 stop

SDF4:41 pmLouisville Intl

Aug 10

SDF2:34 pmLouisville Intl

4h 59m

1 stop

MDW6:33 pmChicago Midway

$255

Delta

Aug 1

MDW6:00 amChicago Midway

4h 09m

1 stop

BNA10:09 amNashville Intl

Aug 8

BNA10:59 amNashville Intl

4h 39m

1 stop

MDW3:38 pmChicago Midway

$257

Frontier flights from Chicago Midway Airport to Kentucky

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

Frontier

Aug 16

MDW11:06 amChicago Midway

23h 42m

1 stop

CVG11:48 amCincinnati Cinci./N. Kentucky

Aug 23

CVG12:26 pmCincinnati Cinci./N. Kentucky

11h 21m

1 stop

MDW10:47 pmChicago Midway

$248

Frontier

Jul 23

MDW12:11 pmChicago Midway

22h 37m

1 stop

CVG11:48 amCincinnati Cinci./N. Kentucky

Jul 26

CVG12:18 pmCincinnati Cinci./N. Kentucky

10h 45m

1 stop

MDW10:03 pmChicago Midway

$249

Frontier

Sep 11

MDW1:02 pmChicago Midway

9h 57m

1 stop

CVG11:59 pmCincinnati Cinci./N. Kentucky

Sep 13

CVG12:48 pmCincinnati Cinci./N. Kentucky

10h 10m

1 stop

MDW9:58 pmChicago Midway

$250

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

Sun 8/9

2:49 pm-5:19 pm

Nonstop1h 30m

Knoxville McGhee Tyson

Thu 8/13

1:23 pm-1:59 pm

Nonstop1h 36m

$155

Quickest round-trip

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Sat 8/15

3:25 pm-5:35 pm

Nonstop1h 10m

Cincinnati Cinci./N. Kentucky

Sat 8/22

8:20 am-8:25 am

Nonstop1h 05m

$157

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Thu 7/30

2:48 pm-5:18 pm

Nonstop1h 30m

Knoxville McGhee Tyson

Thu 8/6

1:23 pm-1:59 pm

Nonstop1h 36m

$159

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Sat 8/15

2:25 pm-6:50 pm

1 stop3h 25m

Cincinnati Cinci./N. Kentucky

Sat 8/22

8:20 am-8:25 am

Nonstop1h 05m

$167

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Sat 8/15

8:00 am-10:25 am

Nonstop1h 25m

Cincinnati Cinci./N. Kentucky

Sat 8/22

6:40 am-1:20 pm

2 stops7h 40m

$172

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Sat 8/8

8:00 am-10:25 am

Nonstop1h 25m

Cincinnati Cinci./N. Kentucky

Mon 8/10

8:10 am-8:15 am

Nonstop1h 05m

$176

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Sat 8/8

9:24 am-4:41 pm

1 stop6h 17m

Louisville Intl

Mon 8/10

2:34 pm-6:33 pm

1 stop4h 59m

$255

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sat 8/1

6:00 am-10:09 am

1 stop4h 09m

Nashville Intl

Sat 8/8

10:59 am-3:38 pm

1 stop4h 39m

$257

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Thu 8/27

9:26 pm-9:01 am

1 stop11h 35m

Nashville Intl

Mon 8/31

9:56 am-8:31 pm

1 stop10h 35m

$258

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Thu 8/20

9:26 pm-9:01 am

1 stop11h 35m

Nashville Intl

Thu 8/27

9:56 am-8:31 pm

1 stop10h 35m

$260

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 month to fly to Kentucky?

If you’re not able to fly to Kentucky in August, then January is your next best option. Flight prices from Chicago Midway Airport to Kentucky during January average around $0.

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

Our data shows that Wednesday is the least expensive day to fly to Kentucky. Tickets to fly out on this day can be as low as $241. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $412. 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 $256. 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 Airport to Kentucky flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport 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	$230
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 $230. The best round-trip flight deal from Chicago Midway Airport to Kentucky found on momondo in the last 72 hours is $286.

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 July 2026, there are 2 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 MAX 8, representing 17.58% of all bookings. The subsequent popular models are Canadair (Bombardier) Regional Jet CRJ-550 at 13.74%, Embraer 175 (Enhanced Winglets) at 13.19%, and Embraer 175 at 12.64%.

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 7.9 4,251 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.