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

As of October 2026, there are 1 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?

8 flights are operational weekly from Chicago Midway Airport to Kentucky as of October 2026. The most popular departure day for this route is Mon, with 25% of flights per week taking off on this day.

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

Delta, Southwest, and Allegiant Air are the most popular carriers operating from Chicago Midway 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 October 2026, there is 1 operator 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.

$99 Cheap Flights from Chicago Midway Airport to Kentucky in 2026/27

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.

7:55 am - 10:10 amMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

8:20 am - 8:35 amSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

$197Southwest

Thu, Oct 22 - Mon, Oct 26

6:55 pm - 9:10 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

8:20 am - 8:35 amSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

$197Southwest

Thu, Oct 22 - Mon, Oct 26

6:15 pm - 8:30 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

8:50 am - 9:05 amSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

$197Southwest

Mon, Dec 7 - Tue, Dec 15

1:05 pm - 3:20 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

12:35 pm - 12:50 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

$197Southwest

Wed, Oct 28 - Sat, Oct 31

7:50 am - 10:05 amMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

3:35 pm - 3:50 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

$197Southwest

Wed, Oct 28 - Thu, Oct 29

12:50 pm - 3:05 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

5:00 pm - 5:25 pmSDF Louisville Intl-MDW Chicago Midway

1h 25mnonstop

$197Southwest

Thu, Nov 5 - Sat, Nov 7

6:55 pm - 9:10 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

7:50 pm - 8:05 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

$197Southwest

Thu, Oct 22 - Mon, Oct 26

12:50 pm - 3:05 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

3:25 pm - 7:40 pmSDF Louisville Intl-MDW Chicago Midway

5h 15m1 stop Baltimore/Washington

$207Southwest

Thu, Nov 5 - Sat, Nov 7

1:05 pm - 7:14 pmMDW Chicago Midway-SDF Louisville Intl

5h 09m1 stop Atlanta Hartsfield-Jackson

3:18 pm - 6:01 pmSDF Louisville Intl-MDW Chicago Midway

3h 43m1 stop Detroit Metropolitan Wayne County

$217Delta

Wed, Nov 18 - Mon, Dec 7

5:29 pm - 10:46 pmMDW Chicago Midway-SDF Louisville Intl

4h 17m1 stop Minneapolis St Paul

11:45 am - 3:04 pmSDF Louisville Intl-MDW Chicago Midway

4h 19m1 stop Atlanta Hartsfield-Jackson

$217Delta

Tue, Nov 17 - Sat, Dec 5

Cheap last minute flights

Enter your travel dates to find the best prices.

6:04 am - 11:58 amMDW Chicago Midway-LEX Lexington Blue Grass

4h 54m1 stop Atlanta Hartsfield-Jackson

7:45 am - 12:47 pmLEX Lexington Blue Grass-MDW Chicago Midway

6h 02m1 stop Detroit Metropolitan Wayne County

$379Delta

Wed, Oct 7 - Tue, Oct 13

6:04 am - 11:58 amMDW Chicago Midway-LEX Lexington Blue Grass

4h 54m1 stop Atlanta Hartsfield-Jackson

7:45 am - 12:47 pmLEX Lexington Blue Grass-MDW Chicago Midway

6h 02m1 stop Detroit Metropolitan Wayne County

$409Delta

Wed, Oct 7 - Mon, Oct 12

6:00 pm - 8:15 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

8:35 am - 8:50 amSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

$541Southwest

Tue, Oct 6 - Wed, Oct 7

7:50 am - 10:05 amMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

2:05 pm - 2:20 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

$541Southwest

Tue, Oct 6 - Tue, Oct 6

7:50 am - 10:05 amMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

5:05 pm - 5:25 pmSDF Louisville Intl-MDW Chicago Midway

1h 20mnonstop

$541Southwest

Tue, Oct 6 - Sat, Oct 10

6:00 pm - 8:15 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

3:00 pm - 10:20 pmSDF Louisville Intl-MDW Chicago Midway

8h 20m1 stop Dallas Love Field

$551Southwest

Tue, Oct 6 - Wed, Oct 7

7:40 am - 12:15 pmMDW Chicago Midway-SDF Louisville Intl

3h 35m1 stop Nashville Intl

2:05 pm - 2:20 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

$551Southwest

Tue, Oct 6 - Tue, Oct 6

1:05 pm - 3:20 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

4:35 pm - 9:45 pmSDF Louisville Intl-MDW Chicago Midway

6h 10m1 stop Nashville Intl

$551Southwest

Tue, Oct 6 - Sat, Oct 10

6:00 pm - 8:15 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

10:55 am - 5:50 pmSDF Louisville Intl-MDW Chicago Midway

7h 55m2 stops Baltimore/Washington Greater Rochester Intl

$556Southwest

Tue, Oct 6 - Sat, Oct 10

7:55 am - 4:30 pmMDW Chicago Midway-SDF Louisville Intl

7h 35m2 stops Buffalo Baltimore/Washington

8:35 am - 8:50 amSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

$556Southwest

Tue, Oct 6 - Wed, Oct 7

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Southwest flights from Chicago Midway Airport to Kentucky

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

Southwest

Oct 22

MDW6:55 pmChicago Midway

1h 15m

SDF9:10 pmLouisville Intl

Oct 26

SDF8:20 amLouisville Intl

1h 15m

MDW8:35 amChicago Midway

$197

Southwest

Oct 22

MDW7:55 amChicago Midway

1h 15m

SDF10:10 amLouisville Intl

Oct 26

SDF5:10 pmLouisville Intl

5h 50m

1 stop

MDW10:00 pmChicago Midway

$207

Southwest

Oct 28

MDW1:05 pmChicago Midway

1h 15m

SDF3:20 pmLouisville Intl

Oct 31

SDF7:00 amLouisville Intl

9h 40m

2 stops

MDW3:40 pmChicago Midway

$212

Delta flights from Chicago Midway Airport to Kentucky

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

Delta

Nov 16

MDW1:05 pmChicago Midway

5h 09m

1 stop

SDF7:14 pmLouisville Intl

Dec 1

SDF3:18 pmLouisville Intl

3h 43m

1 stop

MDW6:01 pmChicago Midway

$217

Delta

Oct 27

MDW12:49 pmChicago Midway

5h 21m

1 stop

SDF7:10 pmLouisville Intl

Oct 30

SDF7:05 amLouisville Intl

5h 49m

1 stop

MDW11:54 amChicago Midway

$234

Delta

Oct 27

MDW6:04 amChicago Midway

5h 50m

1 stop

SDF12:54 pmLouisville Intl

Oct 29

SDF7:05 amLouisville Intl

5h 49m

1 stop

MDW11:54 amChicago Midway

$261

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

Quickest round-trip

ChicagoLouisville

MDW Chicago Midway - SDF Louisville Intl

MDWSDF

Chicago Midway

Thu 10/22

7:55 am-10:10 am

Nonstop1h 15m

Louisville Intl

Mon 10/26

8:20 am-8:35 am

Nonstop1h 15m

$197

ChicagoLouisville

MDW Chicago Midway - SDF Louisville Intl

MDWSDF

Chicago Midway

Thu 10/22

6:55 pm-9:10 pm

Nonstop1h 15m

Louisville Intl

Mon 10/26

8:20 am-8:35 am

Nonstop1h 15m

$197

ChicagoLouisville

MDW Chicago Midway - SDF Louisville Intl

MDWSDF

Chicago Midway

Mon 12/7

6:15 pm-8:30 pm

Nonstop1h 15m

Louisville Intl

Tue 12/15

8:50 am-9:05 am

Nonstop1h 15m

$197

ChicagoLouisville

MDW Chicago Midway - SDF Louisville Intl

MDWSDF

Chicago Midway

Wed 10/28

1:05 pm-3:20 pm

Nonstop1h 15m

Louisville Intl

Sat 10/31

12:35 pm-12:50 pm

Nonstop1h 15m

$197

ChicagoLouisville

MDW Chicago Midway - SDF Louisville Intl

MDWSDF

Chicago Midway

Wed 10/28

7:50 am-10:05 am

Nonstop1h 15m

Louisville Intl

Thu 10/29

3:35 pm-3:50 pm

Nonstop1h 15m

$197

ChicagoLouisville

MDW Chicago Midway - SDF Louisville Intl

MDWSDF

Chicago Midway

Thu 11/5

12:50 pm-3:05 pm

Nonstop1h 15m

Louisville Intl

Sat 11/7

5:00 pm-5:25 pm

Nonstop1h 25m

$197

ChicagoLouisville

MDW Chicago Midway - SDF Louisville Intl

MDWSDF

Chicago Midway

Thu 10/22

6:55 pm-9:10 pm

Nonstop1h 15m

Louisville Intl

Mon 10/26

7:50 pm-8:05 pm

Nonstop1h 15m

$197

ChicagoLouisville

MDW Chicago Midway - SDF Louisville Intl

MDWSDF

Chicago Midway

Thu 11/5

12:50 pm-3:05 pm

Nonstop1h 15m

Louisville Intl

Sat 11/7

3:25 pm-7:40 pm

1 stop5h 15m

$207

ChicagoLouisville

MDW Chicago Midway - SDF Louisville Intl

MDWSDF

Chicago Midway

Wed 11/18

1:05 pm-7:14 pm

1 stop5h 09m

Louisville Intl

Mon 12/7

3:18 pm-6:01 pm

1 stop3h 43m

$217

ChicagoLouisville

MDW Chicago Midway - SDF Louisville Intl

MDWSDF

Chicago Midway

Tue 11/17

5:29 pm-10:46 pm

1 stop4h 17m

Louisville Intl

Sat 12/5

11:45 am-3:04 pm

1 stop4h 19m

$217

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 November, 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 $266. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $521. 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 morning. momondo users have found flights departing from Chicago Midway Airport to Kentucky in the morning for as low as $345. 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 $521.

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	$99
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 $99. The best round-trip flight deal from Chicago Midway Airport to Kentucky found on momondo in the last 72 hours is $197.

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).

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 October 2026, there is 1 operator 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 16.22% of all bookings. The subsequent popular models are Embraer 175 at 12.61%, Embraer 175 (Enhanced Winglets) at 12.16%, and Canadair (Bombardier) Regional Jet CRJ-550 at 12.16%.

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 $206	Free Cancellation	Rating 7.9 4,215 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.