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Cheap flights from Kentucky to Chicago from $67

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 2/26. 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.
Allegiant Air Logo
1:22 pm - 1:57 pm
TYS
-
MDW
1h 35mnonstop
Allegiant Air Logo
2:47 pm - 5:13 pm
MDW
-
TYS
1h 26mnonstop
$132Allegiant Air
Thu, May 21 - Thu, May 28
Allegiant Air Logo
1:22 pm - 1:57 pm
TYS
-
MDW
1h 35mnonstop
Allegiant Air Logo
2:47 pm - 5:13 pm
MDW
-
TYS
1h 26mnonstop
$138Allegiant Air
Thu, May 21 - Sun, May 31
Delta Logo
7:15 pm - 10:28 pm
TRI
-
MDW
4h 13m
1 stop
Delta Logo
6:30 am - 12:53 pm
MDW
-
TRI
5h 23m
1 stop
$159Delta
Fri, May 1 - Sat, May 9
Delta Logo
1:45 pm - 5:22 pm
TRI
-
MDW
4h 37m
1 stop
Delta Logo
6:00 am - 1:00 pm
MDW
-
TRI
6h 00m
1 stop
$169Delta
Tue, Mar 10 - Tue, Mar 17
Southwest Logo
8:55 am - 9:15 am
SDF
-
MDW
1h 20mnonstop
Southwest Logo
6:15 pm - 8:30 pm
MDW
-
SDF
1h 15mnonstop
$177Southwest
Tue, Mar 10 - Wed, Mar 11
Southwest Logo
7:05 pm - 7:25 pm
SDF
-
MDW
1h 20mnonstop
Southwest Logo
3:35 pm - 11:30 pm
MDW
-
SDF
6h 55m
1 stop
$187Southwest
Tue, Mar 10 - Wed, Mar 11
Frontier Logo
1:07 pm - 10:29 pm
CVG
-
MDW
10h 22m
1 stop
Frontier Logo
9:51 pm - 6:33 pm
MDW
-
CVG
19h 42m
2 stops
$193Frontier
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
6:00 am - 4:13 pm
BNA
-
MDW
10h 13m
1 stop
Multiple Airlines Logo
7:30 am - 4:52 pm
MDW
-
BNA
33h 22m
2 stops
$194Multiple Airlines
Sat, May 2 - Tue, May 5
Frontier Logo
1:49 pm - 2:55 pm
BNA
-
MDW
25h 06m
1 stop
Frontier Logo
8:15 am - 4:49 pm
MDW
-
BNA
8h 34m
1 stop
$202Frontier
Fri, Feb 20 - Mon, Feb 23
Multiple Airlines Logo
6:15 am - 3:52 pm
BNA
-
MDW
9h 37m
1 stop
Multiple Airlines Logo
9:51 pm - 10:41 am
MDW
-
BNA
12h 50m
1 stop
$204Multiple Airlines
Thu, Mar 12 - Mon, Mar 16

Frontier flights from Kentucky to Chicago Midway Airport

Our best Frontier deals on Kentucky to Chicago Midway Airport flight tickets
Frontier
Mar 5
CVG1:07 pmCincinnati Cinci./N. Kentucky
10h 22m
1 stop
MDW10:29 pmChicago Midway
Mar 9
MDW9:51 pmChicago Midway
19h 42m
2 stops
CVG6:33 pmCincinnati Cinci./N. Kentucky
$193
Frontier
Apr 17
CVG1:05 pmCincinnati Cinci./N. Kentucky
10h 16m
1 stop
MDW10:21 pmChicago Midway
Apr 19
MDW6:00 amChicago Midway
11h 36m
1 stop
CVG6:36 pmCincinnati Cinci./N. Kentucky
$202
Frontier
Mar 14
CVG1:14 pmCincinnati Cinci./N. Kentucky
8h 07m
1 stop
MDW8:21 pmChicago Midway
Mar 16
MDW9:51 pmChicago Midway
8h 32m
1 stop
CVG7:23 amCincinnati Cinci./N. Kentucky
$207

Southwest flights from Kentucky to Chicago Midway Airport

Our best Southwest deals on Kentucky to Chicago Midway Airport flight tickets
Southwest
Mar 10
SDF8:55 amLouisville Intl
1h 20m
MDW9:15 amChicago Midway
Mar 11
MDW6:15 pmChicago Midway
1h 15m
SDF8:30 pmLouisville Intl
$177
Southwest
Mar 10
SDF7:05 pmLouisville Intl
1h 20m
MDW7:25 pmChicago Midway
Mar 11
MDW3:35 pmChicago Midway
6h 55m
1 stop
SDF11:30 pmLouisville Intl
$187
Southwest
Mar 5
CVG7:15 pmCincinnati Cinci./N. Kentucky
5h 50m
1 stop
MDW12:05 amChicago Midway
Mar 9
MDW6:35 amChicago Midway
5h 10m
1 stop
CVG12:45 pmCincinnati Cinci./N. Kentucky
$191

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 February 13, 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

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Thu 5/21

1:22 pm-1:57 pm

Nonstop1h 35m

Chicago Midway

Thu 5/28

2:47 pm-5:13 pm

Nonstop1h 26m

$132

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Thu 5/21

1:22 pm-1:57 pm

Nonstop1h 35m

Chicago Midway

Sun 5/31

2:47 pm-5:13 pm

Nonstop1h 26m

$138

BlountvilleChicago

TRI - MDW

TRIMDW

Blountville Tri Cities TN/VA

Fri 5/1

7:15 pm-10:28 pm

1 stop4h 13m

Chicago Midway

Sat 5/9

6:30 am-12:53 pm

1 stop5h 23m

$159

BlountvilleChicago

TRI - MDW

TRIMDW

Blountville Tri Cities TN/VA

Tue 3/10

1:45 pm-5:22 pm

1 stop4h 37m

Chicago Midway

Tue 3/17

6:00 am-1:00 pm

1 stop6h 00m

$169

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 3/10

8:55 am-9:15 am

Nonstop1h 20m

Chicago Midway

Wed 3/11

6:15 pm-8:30 pm

Nonstop1h 15m

$177

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 3/10

7:05 pm-7:25 pm

Nonstop1h 20m

Chicago Midway

Wed 3/11

3:35 pm-11:30 pm

1 stop6h 55m

$187

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 3/5

1:07 pm-10:29 pm

1 stop10h 22m

Chicago Midway

Mon 3/9

9:51 pm-6:33 pm

2 stops19h 42m

$193

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Sat 5/2

6:00 am-4:13 pm

1 stop10h 13m

Chicago Midway

Tue 5/5

7:30 am-4:52 pm

2 stops33h 22m

$194

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Fri 2/20

1:49 pm-2:55 pm

1 stop25h 06m

Chicago Midway

Mon 2/23

8:15 am-4:49 pm

1 stop8h 34m

$202

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 3/12

6:15 am-3:52 pm

1 stop9h 37m

Chicago Midway

Mon 3/16

9:51 pm-10:41 am

1 stop12h 50m

$204

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 month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Kentucky, with most prices found around $144. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Kentucky during the month January is also very affordable. Most momondo users find prices during this month for around $175.

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 $368. 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 $303 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $399. 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 53% 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

$190

Fastest flight time

1h 05m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Kentucky in the past 72 hours is $190. The best round-trip flight deal from Kentucky to Chicago Midway Airport found on momondo in the last 72 hours is $348.
The fastest flight from Kentucky to Chicago Midway Airport takes 1h 05m
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
4,283 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Schererville
Valparaiso
Munster
Crown Point
Chesterton
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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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