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Cheap flights from Kentucky to Chicago from $48

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.
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
$79Allegiant Air
Thu, May 21 - Sun, May 24
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
$83Allegiant Air
Thu, May 21 - Sun, May 24
Southwest Logo
8:20 pm - 8:30 pm
CVG
-
MDW
1h 10mnonstop
Southwest Logo
5:05 pm - 11:00 pm
MDW
-
CVG
4h 55m
1 stop
$201Southwest
Mon, Jun 1 - Mon, Jun 8
Delta Logo
4:26 pm - 10:17 pm
CVG
-
MDW
6h 51m
1 stop
Delta Logo
9:17 am - 4:42 pm
MDW
-
CVG
6h 25m
2 stops
$202Delta
Tue, Jun 23 - Tue, Jun 30
Frontier Logo
12:46 pm - 10:02 pm
CVG
-
MDW
10h 16m
1 stop
Frontier Logo
6:00 am - 8:35 pm
MDW
-
CVG
13h 35m
2 stops
$203Frontier
Mon, Jun 1 - Wed, Jun 3
Delta Logo
8:23 am - 12:46 pm
CVG
-
MDW
5h 23m
1 stop
Delta Logo
9:17 am - 1:35 pm
MDW
-
CVG
3h 18m
1 stop
$204Delta
Mon, Jun 8 - Tue, Jun 16
Southwest Logo
1:40 pm - 7:15 pm
CVG
-
MDW
6h 35m
2 stops
Southwest Logo
7:05 pm - 9:15 pm
MDW
-
CVG
1h 10mnonstop
$206Southwest
Sat, Jun 6 - Mon, Jun 8
Frontier Logo
12:24 pm - 10:11 pm
CVG
-
MDW
10h 47m
1 stop
Frontier Logo
6:00 am - 11:47 am
MDW
-
CVG
4h 47m
1 stop
$210Frontier
Tue, Jun 9 - Sat, Jun 13
Multiple Airlines Logo
11:48 am - 8:24 am
LEX
-
MDW
21h 36m
1 stop
Multiple Airlines Logo
6:00 am - 2:15 pm
MDW
-
LEX
31h 15m
2 stops
$343Multiple Airlines
Sat, May 23 - Wed, May 27
Multiple Airlines Logo
11:46 am - 8:33 pm
EVV
-
MDW
8h 47m
1 stop
Multiple Airlines Logo
12:27 pm - 3:49 pm
MDW
-
EVV
27h 22m
2 stops
$356Multiple Airlines
Fri, Jun 19 - Tue, Jun 30

Frontier flights from Kentucky to Chicago Midway Airport

Our best Frontier deals on Kentucky to Chicago Midway Airport flight tickets
Frontier
Jun 1
CVG12:46 pmCincinnati Cinci./N. Kentucky
10h 16m
1 stop
MDW10:02 pmChicago Midway
Jun 3
MDW6:00 amChicago Midway
13h 35m
2 stops
CVG8:35 pmCincinnati Cinci./N. Kentucky
$203
Frontier
Jun 9
CVG12:24 pmCincinnati Cinci./N. Kentucky
10h 47m
1 stop
MDW10:11 pmChicago Midway
Jun 13
MDW6:00 amChicago Midway
4h 47m
1 stop
CVG11:47 amCincinnati Cinci./N. Kentucky
$210
Frontier
Jul 23
CVG12:27 pmCincinnati Cinci./N. Kentucky
10h 41m
1 stop
MDW10:08 pmChicago Midway
Jul 27
MDW12:11 pmChicago Midway
22h 02m
1 stop
CVG11:13 amCincinnati Cinci./N. Kentucky
$213

Delta flights from Kentucky to Chicago Midway Airport

Our best Delta deals on Kentucky to Chicago Midway Airport flight tickets
Delta
Jun 23
CVG4:26 pmCincinnati Cinci./N. Kentucky
6h 51m
1 stop
MDW10:17 pmChicago Midway
Jun 30
MDW9:17 amChicago Midway
6h 25m
2 stops
CVG4:42 pmCincinnati Cinci./N. Kentucky
$202
Delta
Jun 8
CVG8:23 amCincinnati Cinci./N. Kentucky
5h 23m
1 stop
MDW12:46 pmChicago Midway
Jun 16
MDW9:17 amChicago Midway
3h 18m
1 stop
CVG1:35 pmCincinnati Cinci./N. Kentucky
$204
Delta
Jul 28
CVG5:34 amCincinnati Cinci./N. Kentucky
8h 04m
2 stops
MDW12:38 pmChicago Midway
Aug 1
MDW6:35 pmChicago Midway
3h 12m
1 stop
CVG10:47 pmCincinnati Cinci./N. Kentucky
$209

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 May 11, 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

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Thu 5/21

1:22 pm-1:57 pm

Nonstop1h 35m

Chicago Midway

Sun 5/24

2:47 pm-5:13 pm

Nonstop1h 26m

$79

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Thu 5/21

1:22 pm-1:57 pm

Nonstop1h 35m

Chicago Midway

Sun 5/24

2:47 pm-5:13 pm

Nonstop1h 26m

$83

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Mon 6/1

8:20 pm-8:30 pm

Nonstop1h 10m

Chicago Midway

Mon 6/8

5:05 pm-11:00 pm

1 stop4h 55m

$201

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 6/23

4:26 pm-10:17 pm

1 stop6h 51m

Chicago Midway

Tue 6/30

9:17 am-4:42 pm

2 stops6h 25m

$202

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Mon 6/1

12:46 pm-10:02 pm

1 stop10h 16m

Chicago Midway

Wed 6/3

6:00 am-8:35 pm

2 stops13h 35m

$203

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Mon 6/8

8:23 am-12:46 pm

1 stop5h 23m

Chicago Midway

Tue 6/16

9:17 am-1:35 pm

1 stop3h 18m

$204

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 6/6

1:40 pm-7:15 pm

2 stops6h 35m

Chicago Midway

Mon 6/8

7:05 pm-9:15 pm

Nonstop1h 10m

$206

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 6/9

12:24 pm-10:11 pm

1 stop10h 47m

Chicago Midway

Sat 6/13

6:00 am-11:47 am

1 stop4h 47m

$210

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 5/23

11:48 am-8:24 am

1 stop21h 36m

Chicago Midway

Wed 5/27

6:00 am-2:15 pm

2 stops31h 15m

$343

EvansvilleChicago

EVV - MDW

EVVMDW

Evansville Dress Regional

Fri 6/19

11:46 am-8:33 pm

1 stop8h 47m

Chicago Midway

Tue 6/30

12:27 pm-3:49 pm

2 stops27h 22m

$356

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 February is, on average, the cheapest month to fly to Chicago Midway Airport from Kentucky, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Kentucky during the month January is also very affordable. Most momondo users find prices during this month for around $67.

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 $430.

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 $373 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $413. 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

Can stopping save me money on Kentucky to Chicago Midway Airport flights?

You could potentially save up to 36% 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

$203

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 $203. The best round-trip flight deal from Kentucky to Chicago Midway Airport found on momondo in the last 72 hours is $358.
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

Frequently asked questions about flying from Kentucky to Chicago Midway Airport

  • 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 $77Free CancellationRating
8.0
4,298 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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Hammond
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Portage
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Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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