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Cheap flights from Kentucky to Chicago from $49

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 1/1. 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
6:45 am - 7:10 amSDF-MDW
1h 25mnonstop
Southwest Logo
9:55 am - 12:10 pmMDW-SDF
1h 15mnonstop
$99Southwest
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Wed, Jan 14 - Sat, Jan 17
Southwest Logo
1:50 pm - 2:05 pmSDF-MDW
1h 15mnonstop
Southwest Logo
10:05 am - 12:30 pmMDW-SDF
1h 25mnonstop
$101Southwest
Find Deal
Thu, Dec 4 - Mon, Dec 8
Delta Logo
6:00 am - 12:34 pmSDF-MDW
7h 34m2 stops
Delta Logo
9:34 am - 1:49 pmMDW-SDF
3h 15m1 stop
$162Delta
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Wed, Dec 3 - Tue, Dec 9
Delta Logo
6:40 am - 11:06 amSDF-MDW
5h 26m1 stop
Delta Logo
5:31 pm - 11:55 pmMDW-SDF
5h 24m1 stop
$167Delta
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Thu, Jan 1 - Mon, Jan 5
Frontier Logo
12:02 pm - 7:42 pmCVG-MDW
8h 40m1 stop
Frontier Logo
6:15 am - 10:43 amMDW-CVG
27h 28m1 stop
$179Frontier
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Fri, Dec 5 - Sun, Dec 7
Frontier Logo
11:59 am - 6:08 pmCVG-MDW
7h 09m1 stop
Frontier Logo
6:37 pm - 10:52 amMDW-CVG
15h 15m1 stop
$183Frontier
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Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
3:27 pm - 9:27 amCVG-MDW
19h 00m1 stop
Multiple Airlines Logo
6:00 am - 6:42 pmMDW-CVG
11h 42m1 stop
$193Multiple Airlines
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Sat, Jan 17 - Mon, Jan 26
Multiple Airlines Logo
9:03 pm - 1:01 pmCVG-MDW
40h 58m2 stops
Multiple Airlines Logo
7:44 am - 1:08 amMDW-CVG
16h 24m1 stop
$200Multiple Airlines
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Tue, Dec 2 - Tue, Dec 9
Allegiant Air Logo
5:49 pm - 6:46 pmTYS-MDW
25h 57m2 stops
Allegiant Air Logo
2:11 pm - 4:36 pmMDW-TYS
1h 25mnonstop
$213Allegiant Air
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Thu, Nov 20 - Mon, Nov 24
Allegiant Air Logo
6:18 pm - 6:54 pmTYS-MDW
1h 36mnonstop
Allegiant Air Logo
4:24 pm - 6:49 pmMDW-TYS
1h 25mnonstop
$289Allegiant Air
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Wed, Nov 26 - Sun, Nov 30

Southwest flights from Kentucky to Chicago Midway Airport

Our best Southwest deals on Kentucky to Chicago Midway Airport flight tickets
Southwest
Jan 14
SDF6:45 amLouisville Intl
1h 25m
MDW7:10 amChicago Midway
Jan 17
MDW9:55 amChicago Midway
1h 15m
SDF12:10 pmLouisville Intl
$99
Find similar
Southwest
Dec 4
SDF1:50 pmLouisville Intl
1h 15m
MDW2:05 pmChicago Midway
Dec 8
MDW10:05 amChicago Midway
1h 25m
SDF12:30 pmLouisville Intl
$101
Find similar
Southwest
Jan 14
SDF12:50 pmLouisville Intl
7h 10m
1 stop
MDW7:00 pmChicago Midway
Jan 17
MDW9:55 amChicago Midway
1h 15m
SDF12:10 pmLouisville Intl
$109
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Delta flights from Kentucky to Chicago Midway Airport

Our best Delta deals on Kentucky to Chicago Midway Airport flight tickets
Delta
Dec 3
SDF6:00 amLouisville Intl
7h 34m
2 stops
MDW12:34 pmChicago Midway
Dec 9
MDW9:34 amChicago Midway
3h 15m
1 stop
SDF1:49 pmLouisville Intl
$162
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Delta
Dec 11
BNA6:00 amNashville Intl
6h 34m
1 stop
MDW12:34 pmChicago Midway
Jan 6
MDW6:45 amChicago Midway
6h 14m
1 stop
BNA12:59 pmNashville Intl
$167
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Delta
Dec 2
BNA6:00 amNashville Intl
6h 34m
1 stop
MDW12:34 pmChicago Midway
Dec 9
MDW10:49 amChicago Midway
6h 18m
1 stop
BNA5:07 pmNashville Intl
$168
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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 November 6, 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

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 1/14

6:45 am-7:10 am

Nonstop1h 25m

Chicago Midway

Sat 1/17

9:55 am-12:10 pm

Nonstop1h 15m

$99

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 12/4

1:50 pm-2:05 pm

Nonstop1h 15m

Chicago Midway

Mon 12/8

10:05 am-12:30 pm

Nonstop1h 25m

$101

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 12/3

6:00 am-12:34 pm

2 stops7h 34m

Chicago Midway

Tue 12/9

9:34 am-1:49 pm

1 stop3h 15m

$162

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 1/1

6:40 am-11:06 am

1 stop5h 26m

Chicago Midway

Mon 1/5

5:31 pm-11:55 pm

1 stop5h 24m

$167

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Fri 12/5

12:02 pm-7:42 pm

1 stop8h 40m

Chicago Midway

Sun 12/7

6:15 am-10:43 am

1 stop27h 28m

$179

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 12/4

11:59 am-6:08 pm

1 stop7h 09m

Chicago Midway

Sun 12/7

6:37 pm-10:52 am

1 stop15h 15m

$183

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 1/17

3:27 pm-9:27 am

1 stop19h 00m

Chicago Midway

Mon 1/26

6:00 am-6:42 pm

1 stop11h 42m

$193

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 12/2

9:03 pm-1:01 pm

2 stops40h 58m

Chicago Midway

Tue 12/9

7:44 am-1:08 am

1 stop16h 24m

$200

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Thu 11/20

5:49 pm-6:46 pm

2 stops25h 57m

Chicago Midway

Mon 11/24

2:11 pm-4:36 pm

Nonstop1h 25m

$213

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Wed 11/26

6:18 pm-6:54 pm

Nonstop1h 36m

Chicago Midway

Sun 11/30

4:24 pm-6:49 pm

Nonstop1h 25m

$289

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 January is, on average, the cheapest month to fly to Chicago Midway Airport from Kentucky, with most prices found around $132. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Kentucky during the month September is also very affordable. Most momondo users find prices during this month for around $144.

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 $382. 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 $419.

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 $341 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $415. 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

$169

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 $169. The best round-trip flight deal from Kentucky to Chicago Midway Airport found on momondo in the last 72 hours is $331.
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
4,241 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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New Buffalo
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Schererville
Valparaiso
Crown Point
Munster
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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