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Cheap flights from Chicago Midway Airport to Kentucky from $56

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Kentucky departing on 3/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago Midway Airport to Kentucky

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
3:00 pm - 12:59 am
MDW
-
CVG
8h 59m
1 stop
Frontier Logo
1:07 pm - 10:29 pm
CVG
-
MDW
10h 22m
1 stop
$154Frontier
Thu, Feb 19 - Mon, Feb 23
Delta Logo
6:00 am - 12:17 pm
MDW
-
TRI
5h 17m
1 stop
Delta Logo
7:17 pm - 10:31 pm
TRI
-
MDW
4h 14m
1 stop
$157Delta
Wed, Mar 4 - Mon, Mar 9
Frontier Logo
6:15 am - 4:37 pm
MDW
-
CVG
9h 22m
1 stop
Frontier Logo
1:07 pm - 10:29 pm
CVG
-
MDW
10h 22m
1 stop
$160Frontier
Thu, Feb 19 - Mon, Feb 23
Frontier Logo
6:48 pm - 11:33 pm
MDW
-
CVG
27h 45m
1 stop
Frontier Logo
1:07 pm - 7:47 pm
CVG
-
MDW
7h 40m
1 stop
$179Frontier
Fri, Feb 20 - Mon, Feb 23
Frontier Logo
8:00 am - 5:04 pm
MDW
-
CVG
8h 04m
1 stop
Frontier Logo
1:07 pm - 10:29 pm
CVG
-
MDW
10h 22m
1 stop
$181Frontier
Sat, Feb 21 - Mon, Feb 23
Southwest Logo
7:45 pm - 9:15 pm
MDW
-
BNA
1h 30mnonstop
Southwest Logo
10:15 pm - 12:05 am
BNA
-
MDW
1h 50mnonstop
$194Southwest
Wed, Mar 4 - Sat, Mar 7
Southwest Logo
7:45 am - 9:20 am
MDW
-
BNA
1h 35mnonstop
Southwest Logo
7:35 am - 1:55 pm
BNA
-
MDW
6h 20m
2 stops
$197Southwest
Sat, Feb 28 - Tue, Mar 3
Multiple Airlines Logo
7:00 am - 7:48 pm
MDW
-
BNA
12h 48m
2 stops
Multiple Airlines Logo
6:15 am - 2:26 pm
BNA
-
MDW
8h 11m
1 stop
$198Multiple Airlines
Wed, Feb 18 - Fri, Feb 20
Multiple Airlines Logo
2:19 pm - 7:48 pm
MDW
-
BNA
29h 29m
2 stops
Multiple Airlines Logo
2:54 pm - 6:13 pm
BNA
-
MDW
27h 19m
1 stop
$208Multiple Airlines
Mon, Mar 2 - Mon, Mar 9
Allegiant Air Logo
9:23 pm - 9:34 pm
MDW
-
TYS
23h 11m
1 stop
Allegiant Air Logo
1:22 pm - 1:56 pm
TYS
-
MDW
1h 34mnonstop
$261Allegiant Air
Fri, Jun 19 - Sun, Jun 28

Southwest flights from Chicago Midway Airport to Kentucky

Our best Southwest deals on Chicago Midway Airport to Kentucky flight tickets
Southwest
Mar 4
MDW7:45 pmChicago Midway
1h 30m
BNA9:15 pmNashville Intl
Mar 7
BNA10:15 pmNashville Intl
1h 50m
MDW12:05 amChicago Midway
$194
Southwest
Feb 28
MDW7:45 amChicago Midway
1h 35m
BNA9:20 amNashville Intl
Mar 3
BNA7:35 amNashville Intl
6h 20m
2 stops
MDW1:55 pmChicago Midway
$197
Southwest
Mar 4
MDW1:25 pmChicago Midway
3h 20m
1 stop
BNA4:45 pmNashville Intl
Mar 7
BNA10:15 pmNashville Intl
1h 50m
MDW12:05 amChicago Midway
$200

Delta flights from Chicago Midway Airport to Kentucky

Our best Delta deals on Chicago Midway Airport to Kentucky flight tickets
Delta
Mar 4
MDW6:00 amChicago Midway
5h 17m
1 stop
TRI12:17 pmBlountville Tri Cities TN/VA
Mar 9
TRI7:17 pmBlountville Tri Cities TN/VA
4h 14m
1 stop
MDW10:31 pmChicago Midway
$157
Delta
Feb 25
MDW6:00 amChicago Midway
4h 08m
1 stop
TYS11:08 amKnoxville McGhee Tyson
Feb 28
TYS7:38 amKnoxville McGhee Tyson
6h 08m
1 stop
MDW12:46 pmChicago Midway
$209
Delta
Apr 17
MDW6:00 amChicago Midway
6h 23m
1 stop
BNA12:23 pmNashville Intl
Apr 20
BNA4:13 pmNashville Intl
6h 15m
1 stop
MDW10:28 pmChicago Midway
$211

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Kentucky 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 February 5, 2026.
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

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 2/19

3:00 pm-12:59 am

1 stop8h 59m

Cincinnati Cinci./N. Kentucky

Mon 2/23

1:07 pm-10:29 pm

1 stop10h 22m

$154

ChicagoBlountville

MDW - TRI

MDWTRI

Chicago Midway

Wed 3/4

6:00 am-12:17 pm

1 stop5h 17m

Blountville Tri Cities TN/VA

Mon 3/9

7:17 pm-10:31 pm

1 stop4h 14m

$157

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 2/19

6:15 am-4:37 pm

1 stop9h 22m

Cincinnati Cinci./N. Kentucky

Mon 2/23

1:07 pm-10:29 pm

1 stop10h 22m

$160

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Fri 2/20

6:48 pm-11:33 pm

1 stop27h 45m

Cincinnati Cinci./N. Kentucky

Mon 2/23

1:07 pm-7:47 pm

1 stop7h 40m

$179

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Sat 2/21

8:00 am-5:04 pm

1 stop8h 04m

Cincinnati Cinci./N. Kentucky

Mon 2/23

1:07 pm-10:29 pm

1 stop10h 22m

$181

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Wed 3/4

7:45 pm-9:15 pm

Nonstop1h 30m

Nashville Intl

Sat 3/7

10:15 pm-12:05 am

Nonstop1h 50m

$194

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sat 2/28

7:45 am-9:20 am

Nonstop1h 35m

Nashville Intl

Tue 3/3

7:35 am-1:55 pm

2 stops6h 20m

$197

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Wed 2/18

7:00 am-7:48 pm

2 stops12h 48m

Nashville Intl

Fri 2/20

6:15 am-2:26 pm

1 stop8h 11m

$198

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Mon 3/2

2:19 pm-7:48 pm

2 stops29h 29m

Nashville Intl

Mon 3/9

2:54 pm-6:13 pm

1 stop27h 19m

$208

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Fri 6/19

9:23 pm-9:34 pm

1 stop23h 11m

Knoxville McGhee Tyson

Sun 6/28

1:22 pm-1:56 pm

Nonstop1h 34m

$261

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 Kentucky from

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

What is the cheapest month to fly to Kentucky?

If you’re not able to fly to Kentucky in September, then November is your next best option. Flight prices from Chicago Midway Airport to Kentucky during November average around $145.

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

Our data shows that Tuesday is the least expensive day to fly to Kentucky. Tickets to fly out on this day can be as low as $218. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $582. 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 $270. 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 $329.

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

$172

Fastest flight time

1h 05m

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 $172. The best round-trip flight deal from Chicago Midway Airport to Kentucky found on momondo in the last 72 hours is $329.
The fastest flight from Chicago Midway Airport to Kentucky takes 1h 05m
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), Cincinnati Cinci./N. Kentucky (CVG).
Search flight deals

  • 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?

  • 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?

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
SouthwestPriceFrom $124Free CancellationRating
8.0
4,274 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.

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