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Cheap flights from Kentucky to Chicago from $61

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 5/31. 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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0 bags

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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.
Multiple Airlines Logo
9:25 am - 7:52 pm
BNA
-
MDW
10h 27m1 stop
Multiple Airlines Logo
1:00 pm - 3:24 pm
MDW
-
BNA
26h 24m1 stop
$146Multiple Airlines
Fri, Feb 6 - Sun, Feb 8
Frontier Logo
7:14 pm - 2:26 pm
CVG
-
MDW
20h 12m1 stop
Frontier Logo
9:22 pm - 9:25 pm
MDW
-
CVG
23h 03m1 stop
$152Frontier
Thu, Feb 19 - Mon, Feb 23
Delta Logo
7:50 am - 12:46 pm
SDF
-
MDW
5h 56m1 stop
Delta Logo
6:14 pm - 11:50 pm
MDW
-
SDF
4h 36m1 stop
$157Delta
Tue, Feb 3 - Tue, Feb 3
Delta Logo
5:35 am - 12:46 pm
SDF
-
MDW
8h 11m2 stops
Delta Logo
6:14 pm - 11:50 pm
MDW
-
SDF
4h 36m1 stop
$162Delta
Tue, Feb 3 - Tue, Feb 3
Frontier Logo
1:22 pm - 10:19 pm
CVG
-
MDW
9h 57m1 stop
Frontier Logo
1:00 pm - 11:26 pm
MDW
-
CVG
9h 26m1 stop
$162Frontier
Thu, Jan 22 - Mon, Jan 26
Delta Logo
5:33 am - 12:46 pm
SDF
-
MDW
8h 13m2 stops
Delta Logo
9:50 am - 5:50 pm
MDW
-
SDF
7h 00m2 stops
$167Delta
Tue, Feb 17 - Tue, Feb 24
Southwest Logo
6:25 am - 6:55 am
SDF
-
MDW
1h 30mnonstop
Southwest Logo
8:45 pm - 11:00 pm
MDW
-
SDF
1h 15mnonstop
$171Southwest
Thu, Jan 15 - Mon, Jan 19
Southwest Logo
6:30 pm - 6:45 pm
SDF
-
MDW
1h 15mnonstop
Southwest Logo
10:05 am - 5:00 pm
MDW
-
SDF
5h 55m1 stop
$181Southwest
Thu, Jan 22 - Thu, Jan 29
Frontier Logo
10:30 am - 7:52 pm
CVG
-
MDW
10h 22m1 stop
Frontier Logo
1:00 pm - 3:03 pm
MDW
-
CVG
25h 03m1 stop
$186Frontier
Fri, Jan 23 - Fri, Jan 30
Delta Logo
7:50 am - 12:46 pm
SDF
-
MDW
5h 56m1 stop
Delta Logo
6:00 am - 11:37 am
MDW
-
SDF
4h 37m1 stop
$191Delta
Thu, Jan 22 - Thu, Jan 29

Frontier flights from Kentucky to Chicago Midway Airport

Our best Frontier deals on Kentucky to Chicago Midway Airport flight tickets
Frontier
Feb 19
CVG7:14 pmCincinnati Cinci./N. Kentucky
20h 12m
1 stop
MDW2:26 pmChicago Midway
Feb 23
MDW9:22 pmChicago Midway
23h 03m
1 stop
CVG9:25 pmCincinnati Cinci./N. Kentucky
$152
Find similar
Frontier
Jan 22
CVG1:22 pmCincinnati Cinci./N. Kentucky
9h 57m
1 stop
MDW10:19 pmChicago Midway
Jan 26
MDW1:00 pmChicago Midway
9h 26m
1 stop
CVG11:26 pmCincinnati Cinci./N. Kentucky
$162
Find similar
Frontier
Jan 23
CVG10:30 amCincinnati Cinci./N. Kentucky
10h 22m
1 stop
MDW7:52 pmChicago Midway
Jan 30
MDW1:00 pmChicago Midway
25h 03m
1 stop
CVG3:03 pmCincinnati Cinci./N. Kentucky
$186
Find similar

Southwest flights from Kentucky to Chicago Midway Airport

Our best Southwest deals on Kentucky to Chicago Midway Airport flight tickets
Southwest
Jan 15
SDF6:25 amLouisville Intl
1h 30m
MDW6:55 amChicago Midway
Jan 19
MDW8:45 pmChicago Midway
1h 15m
SDF11:00 pmLouisville Intl
$171
Find similar
Southwest
Jan 22
SDF6:30 pmLouisville Intl
1h 15m
MDW6:45 pmChicago Midway
Jan 29
MDW10:05 amChicago Midway
5h 55m
1 stop
SDF5:00 pmLouisville Intl
$181
Find similar
Southwest
Feb 24
CVG7:00 amCincinnati Cinci./N. Kentucky
1h 25m
MDW7:25 amChicago Midway
Mar 4
MDW5:30 pmChicago Midway
1h 10m
CVG7:40 pmCincinnati Cinci./N. Kentucky
$193
Find similar

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 December 27, 2025.
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

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Fri 2/6

9:25 am-7:52 pm

1 stop10h 27m

Chicago Midway

Sun 2/8

1:00 pm-3:24 pm

1 stop26h 24m

$146

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 2/19

7:14 pm-2:26 pm

1 stop20h 12m

Chicago Midway

Mon 2/23

9:22 pm-9:25 pm

1 stop23h 03m

$152

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 2/3

7:50 am-12:46 pm

1 stop5h 56m

Chicago Midway

Tue 2/3

6:14 pm-11:50 pm

1 stop4h 36m

$157

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 2/3

5:35 am-12:46 pm

2 stops8h 11m

Chicago Midway

Tue 2/3

6:14 pm-11:50 pm

1 stop4h 36m

$162

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 1/22

1:22 pm-10:19 pm

1 stop9h 57m

Chicago Midway

Mon 1/26

1:00 pm-11:26 pm

1 stop9h 26m

$162

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 2/17

5:33 am-12:46 pm

2 stops8h 13m

Chicago Midway

Tue 2/24

9:50 am-5:50 pm

2 stops7h 00m

$167

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 1/15

6:25 am-6:55 am

Nonstop1h 30m

Chicago Midway

Mon 1/19

8:45 pm-11:00 pm

Nonstop1h 15m

$171

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 1/22

6:30 pm-6:45 pm

Nonstop1h 15m

Chicago Midway

Thu 1/29

10:05 am-5:00 pm

1 stop5h 55m

$181

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Fri 1/23

10:30 am-7:52 pm

1 stop10h 22m

Chicago Midway

Fri 1/30

1:00 pm-3:03 pm

1 stop25h 03m

$186

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 1/22

7:50 am-12:46 pm

1 stop5h 56m

Chicago Midway

Thu 1/29

6:00 am-11:37 am

1 stop4h 37m

$191

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 October is also very affordable. Most momondo users find prices during this month for around $179.

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 $375. 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 $415.

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 $304 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?

No. A direct flight is the cheapest option for a flight between Kentucky to Chicago Midway Airport.

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

$187

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 $187. The best round-trip flight deal from Kentucky to Chicago Midway Airport found on momondo in the last 72 hours is $326.
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
4,258 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
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Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
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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