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Cheap flights from Kentucky to Chicago from $39

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 10/28. 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

Southwest Logo
7:10 pm - 7:30 pmSDF-MDW
1h 20mnonstop
Southwest Logo
8:35 pm - 10:50 pmMDW-SDF
1h 15mnonstop
$77Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8
Southwest Logo
8:20 am - 10:00 amBNA-MDW
1h 40mnonstop
Southwest Logo
5:40 am - 7:05 amMDW-BNA
1h 25mnonstop
$77Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8
Allegiant Air Logo
6:24 pm - 7:00 pmTYS-MDW
1h 36mnonstop
Allegiant Air Logo
7:50 pm - 10:21 pmMDW-TYS
1h 31mnonstop
$80Allegiant Air
Find Deal
Fri, Sep 12 - Mon, Sep 15
Allegiant Air Logo
6:24 pm - 7:00 pmTYS-MDW
1h 36mnonstop
Allegiant Air Logo
3:16 pm - 5:47 pmMDW-TYS
1h 31mnonstop
$82Allegiant Air
Find Deal
Fri, Sep 26 - Mon, Sep 29
Frontier Logo
8:14 pm - 7:11 amBNA-MDW
10h 57m1 stop
Frontier Logo
8:15 am - 7:27 pmMDW-BNA
11h 12m1 stop
$144Frontier
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Thu, Sep 4 - Mon, Sep 8
Frontier Logo
8:14 pm - 7:11 amBNA-MDW
10h 57m1 stop
Frontier Logo
8:06 am - 7:26 pmMDW-BNA
11h 20m1 stop
$145Frontier
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Thu, Oct 2 - Sun, Oct 5
Logo
6:24 pm - 7:00 pmTYS-MDW
1h 36mnonstop
Logo
8:19 am - 10:34 pmMDW-TYS
13h 15m1 stop
$168
Find Deal
Fri, Sep 19 - Mon, Sep 22
Logo
9:31 pm - 9:18 amTYS-MDW
12h 47m1 stop
Logo
7:50 pm - 10:21 pmMDW-TYS
1h 31mnonstop
$172
Find Deal
Sat, Sep 13 - Mon, Sep 15
Delta Logo
6:00 pm - 9:36 pmSDF-MDW
4h 36m1 stop
Delta Logo
9:35 am - 1:42 pmMDW-SDF
3h 07m1 stop
$177Delta
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Tue, Sep 23 - Wed, Sep 24
Delta Logo
1:58 pm - 6:37 pmBNA-MDW
4h 39m1 stop
Delta Logo
9:35 am - 12:53 pmMDW-BNA
3h 18m1 stop
$177Delta
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Wed, Sep 10 - Tue, Sep 16

Southwest flights from Kentucky to Chicago Midway Airport

Our best Southwest deals on Kentucky to Chicago Midway Airport flight tickets
Southwest
Sep 4
SDF7:10 pmLouisville Intl
1h 20m
MDW7:30 pmChicago Midway
Sep 8
MDW8:35 pmChicago Midway
1h 15m
SDF10:50 pmLouisville Intl
$77
Find similar
Southwest
Sep 4
SDF11:40 amLouisville Intl
7h 25m
1 stop
MDW6:05 pmChicago Midway
Sep 8
MDW8:35 pmChicago Midway
1h 15m
SDF10:50 pmLouisville Intl
$87
Find similar
Southwest
Sep 4
SDF6:25 amLouisville Intl
1h 15m
MDW6:40 amChicago Midway
Sep 8
MDW3:25 pmChicago Midway
7h 05m
2 stops
SDF11:30 pmLouisville Intl
$92
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Allegiant Air flights from Kentucky to Chicago Midway Airport

Our best Allegiant Air deals on Kentucky to Chicago Midway Airport flight tickets
Allegiant Air
Sep 12
TYS6:24 pmKnoxville McGhee Tyson
1h 36m
MDW7:00 pmChicago Midway
Sep 15
MDW7:50 pmChicago Midway
1h 31m
TYS10:21 pmKnoxville McGhee Tyson
$80
Find similar
Allegiant Air
Sep 26
TYS6:24 pmKnoxville McGhee Tyson
1h 36m
MDW7:00 pmChicago Midway
Sep 29
MDW3:16 pmChicago Midway
1h 31m
TYS5:47 pmKnoxville McGhee Tyson
$82
Find similar
Allegiant Air
Sep 5
TYS6:24 pmKnoxville McGhee Tyson
1h 36m
MDW7:00 pmChicago Midway
Sep 8
MDW7:50 pmChicago Midway
1h 31m
TYS10:21 pmKnoxville McGhee Tyson
$86
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 August 14, 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

Thu 9/4

7:10 pm-7:30 pm

Nonstop1h 20m

Chicago Midway

Mon 9/8

8:35 pm-10:50 pm

Nonstop1h 15m

$77

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 9/4

8:20 am-10:00 am

Nonstop1h 40m

Chicago Midway

Mon 9/8

5:40 am-7:05 am

Nonstop1h 25m

$77

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Fri 9/12

6:24 pm-7:00 pm

Nonstop1h 36m

Chicago Midway

Mon 9/15

7:50 pm-10:21 pm

Nonstop1h 31m

$80

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Fri 9/26

6:24 pm-7:00 pm

Nonstop1h 36m

Chicago Midway

Mon 9/29

3:16 pm-5:47 pm

Nonstop1h 31m

$82

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 9/4

8:14 pm-7:11 am

1 stop10h 57m

Chicago Midway

Mon 9/8

8:15 am-7:27 pm

1 stop11h 12m

$144

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 10/2

8:14 pm-7:11 am

1 stop10h 57m

Chicago Midway

Sun 10/5

8:06 am-7:26 pm

1 stop11h 20m

$145

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Fri 9/19

6:24 pm-7:00 pm

Nonstop1h 36m

Chicago Midway

Mon 9/22

8:19 am-10:34 pm

1 stop13h 15m

$168

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Sat 9/13

9:31 pm-9:18 am

1 stop12h 47m

Chicago Midway

Mon 9/15

7:50 pm-10:21 pm

Nonstop1h 31m

$172

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 9/23

6:00 pm-9:36 pm

1 stop4h 36m

Chicago Midway

Wed 9/24

9:35 am-1:42 pm

1 stop3h 07m

$177

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 9/10

1:58 pm-6:37 pm

1 stop4h 39m

Chicago Midway

Tue 9/16

9:35 am-12:53 pm

1 stop3h 18m

$177

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 $197. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Kentucky during the month December is also very affordable. Most momondo users find prices during this month for around $226.

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

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Kentucky. The lowest ticket price found for a Tuesday departure recently was $385. 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 $423.

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

Flying to Chicago Midway Airport from Kentucky at noon is the least expensive time of day to depart. momondo users have found prices as low as $382 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $419. 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 are 1 cabin classes 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

$39

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 $39. The best round-trip flight deal from Kentucky to Chicago Midway Airport found on momondo in the last 72 hours is $77.
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
4,244 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
Hammond
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Portage
Schererville
Valparaiso
Crown Point
Munster
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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