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Cheap flights from Kentucky to Chicago from $52

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Kentucky to Chicago departing on 5/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Kentucky to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:45 am - 8:55 am
CVG
-
MDW
1h 10mnonstop
Southwest Logo
6:10 pm - 8:20 pm
MDW
-
CVG
1h 10mnonstop
$174Southwest
Sat, May 2 - Tue, May 5
Frontier Logo
12:19 pm - 8:07 pm
CVG
-
MDW
8h 48m
1 stop
Frontier Logo
6:00 am - 5:33 pm
MDW
-
CVG
10h 33m
1 stop
$180Frontier
Mon, Apr 13 - Thu, Apr 16
Frontier Logo
12:46 pm - 10:02 pm
CVG
-
MDW
10h 16m
1 stop
Frontier Logo
6:00 am - 11:41 am
MDW
-
CVG
4h 41m
1 stop
$181Frontier
Wed, May 6 - Fri, May 8
Southwest Logo
8:35 am - 8:45 am
CVG
-
MDW
1h 10mnonstop
Southwest Logo
5:30 am - 11:50 am
MDW
-
CVG
5h 20m
1 stop
$184Southwest
Tue, Apr 21 - Thu, Apr 23
Frontier Logo
7:46 pm - 8:52 pm
CVG
-
MDW
26h 06m
2 stops
Frontier Logo
6:00 am - 6:36 pm
MDW
-
CVG
11h 36m
1 stop
$185Frontier
Sat, Apr 25 - Sat, May 2
Multiple Airlines Logo
8:00 am - 10:19 pm
CVG
-
MDW
15h 19m
2 stops
Multiple Airlines Logo
2:15 pm - 5:33 pm
MDW
-
CVG
26h 18m
1 stop
$186Multiple Airlines
Mon, Apr 20 - Wed, Apr 22
Allegiant Air Logo
1:22 pm - 1:56 pm
TYS
-
MDW
1h 34mnonstop
Allegiant Air Logo
2:46 pm - 5:14 pm
MDW
-
TYS
1h 28mnonstop
$193Allegiant Air
Sun, Jun 7 - Sun, Jun 21
Delta Logo
5:54 pm - 10:28 pm
TYS
-
MDW
5h 34m
1 stop
Delta Logo
5:21 pm - 11:54 pm
MDW
-
TYS
5h 33m
1 stop
$230Delta
Fri, Apr 17 - Sat, Apr 18
Allegiant Air Logo
1:22 pm - 1:56 pm
TYS
-
MDW
1h 34mnonstop
Allegiant Air Logo
9:23 pm - 9:34 pm
MDW
-
TYS
23h 11m
1 stop
$234Allegiant Air
Sun, Jun 7 - Fri, Jun 19
Delta Logo
7:19 pm - 10:28 pm
TRI
-
MDW
4h 09m
1 stop
Delta Logo
5:21 pm - 10:32 pm
MDW
-
TRI
4h 11m
1 stop
$249Delta
Thu, Apr 23 - Mon, Apr 27

Allegiant Air flights from Kentucky to Chicago Midway Airport

Our best Allegiant Air deals on Kentucky to Chicago Midway Airport flight tickets
Allegiant Air
Jun 7
TYS1:22 pmKnoxville McGhee Tyson
1h 34m
MDW1:56 pmChicago Midway
Jun 21
MDW2:46 pmChicago Midway
1h 28m
TYS5:14 pmKnoxville McGhee Tyson
$193
Allegiant Air
Jun 7
TYS1:22 pmKnoxville McGhee Tyson
1h 34m
MDW1:56 pmChicago Midway
Jun 19
MDW9:23 pmChicago Midway
23h 11m
1 stop
TYS9:34 pmKnoxville McGhee Tyson
$234
Allegiant Air
Jun 18
TYS1:22 pmKnoxville McGhee Tyson
1h 34m
MDW1:56 pmChicago Midway
Jun 21
MDW2:46 pmChicago Midway
1h 28m
TYS5:14 pmKnoxville McGhee Tyson
$235

Frontier flights from Kentucky to Chicago Midway Airport

Our best Frontier deals on Kentucky to Chicago Midway Airport flight tickets
Frontier
Apr 13
CVG12:19 pmCincinnati Cinci./N. Kentucky
8h 48m
1 stop
MDW8:07 pmChicago Midway
Apr 16
MDW6:00 amChicago Midway
10h 33m
1 stop
CVG5:33 pmCincinnati Cinci./N. Kentucky
$180
Frontier
May 6
CVG12:46 pmCincinnati Cinci./N. Kentucky
10h 16m
1 stop
MDW10:02 pmChicago Midway
May 8
MDW6:00 amChicago Midway
4h 41m
1 stop
CVG11:41 amCincinnati Cinci./N. Kentucky
$181
Frontier
Apr 25
CVG7:46 pmCincinnati Cinci./N. Kentucky
26h 06m
2 stops
MDW8:52 pmChicago Midway
May 2
MDW6:00 amChicago Midway
11h 36m
1 stop
CVG6:36 pmCincinnati Cinci./N. Kentucky
$185

momondo Fare Finder

 
Customize your flight search to find flights from Kentucky to Chicago Midway Airport 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 April 1, 2026.
Use the filters below to find and compare flights from Kentucky to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 5/2

8:45 am-8:55 am

Nonstop1h 10m

Chicago Midway

Tue 5/5

6:10 pm-8:20 pm

Nonstop1h 10m

$174

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Mon 4/13

12:19 pm-8:07 pm

1 stop8h 48m

Chicago Midway

Thu 4/16

6:00 am-5:33 pm

1 stop10h 33m

$180

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Wed 5/6

12:46 pm-10:02 pm

1 stop10h 16m

Chicago Midway

Fri 5/8

6:00 am-11:41 am

1 stop4h 41m

$181

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 4/21

8:35 am-8:45 am

Nonstop1h 10m

Chicago Midway

Thu 4/23

5:30 am-11:50 am

1 stop5h 20m

$184

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 4/25

7:46 pm-8:52 pm

2 stops26h 06m

Chicago Midway

Sat 5/2

6:00 am-6:36 pm

1 stop11h 36m

$185

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Mon 4/20

8:00 am-10:19 pm

2 stops15h 19m

Chicago Midway

Wed 4/22

2:15 pm-5:33 pm

1 stop26h 18m

$186

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Sun 6/7

1:22 pm-1:56 pm

Nonstop1h 34m

Chicago Midway

Sun 6/21

2:46 pm-5:14 pm

Nonstop1h 28m

$193

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Fri 4/17

5:54 pm-10:28 pm

1 stop5h 34m

Chicago Midway

Sat 4/18

5:21 pm-11:54 pm

1 stop5h 33m

$230

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Sun 6/7

1:22 pm-1:56 pm

Nonstop1h 34m

Chicago Midway

Fri 6/19

9:23 pm-9:34 pm

1 stop23h 11m

$234

BlountvilleChicago

TRI - MDW

TRIMDW

Blountville Tri Cities TN/VA

Thu 4/23

7:19 pm-10:28 pm

1 stop4h 09m

Chicago Midway

Mon 4/27

5:21 pm-10:32 pm

1 stop4h 11m

$249

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 Chicago from

How to get the cheapest flight ticket from Kentucky 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 cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Kentucky. The lowest ticket price found for a Saturday departure recently was $366. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Kentucky because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $422.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Kentucky in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $355 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $402. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Kentucky to Chicago Midway flight route?

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

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

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

You could potentially save up to 41% on your flight if you consider stops on a Kentucky to Chicago Midway Airport flight.

Cheap Kentucky to Chicago Midway Airport flight deals and tips

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

Best Price Found

$217

Fastest flight time

1h 10m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Kentucky in the past 72 hours is $217. The best round-trip flight deal from Kentucky to Chicago Midway Airport found on momondo in the last 72 hours is $379.
The fastest flight from Kentucky to Chicago Midway Airport takes 1h 10m
Direct flights go from Kentucky to Chicago Midway Airport every day.
Search flight deals

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

    Prices for flights from Kentucky to Chicago Midway Airport are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Kentucky to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport 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 Chicago Midway Airport. 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 Kentucky to Chicago Midway Airport?

Best airlines flying from Kentucky to Chicago Midway Airport

Compare and see reviews for airlines that fly from Kentucky to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $97Free CancellationRating
8.0
4,335 reviews
Search Southwest flights

Traveling to a place near Chicago?

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Munster
Crown Point
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Porter
Griffith
Saint John

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Kentucky to Chicago for you.

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

All flight searches from Kentucky to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

momondo helps you find the best flight between Kentucky and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Kentucky and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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