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Cheap flights from Kentucky to Chicago from $45

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 11/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Kentucky to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
4:55 pm - 5:05 pmCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
1h 10mnonstop
Southwest Logo
2:00 pm - 8:55 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
5h 55m2 stops Lambert-St Louis Nashville Intl
$172Southwest
Sat, Sep 12 - Wed, Sep 23
Southwest Logo
7:15 pm - 7:25 pmCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
1h 10mnonstop
Southwest Logo
2:35 pm - 10:25 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
6h 50m2 stops Myrtle Beach Intl Baltimore/Washington
$172Southwest
Wed, Sep 9 - Fri, Sep 11
Southwest Logo
5:25 pm - 10:25 pmCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
6h 00m1 stop Nashville Intl
Southwest Logo
5:55 am - 12:15 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
5h 20m1 stop Nashville Intl
$176Southwest
Fri, Sep 11 - Thu, Sep 17
Delta Logo
11:45 am - 4:57 pmCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
6h 12m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 3:14 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
4h 45m1 stop Detroit Metropolitan Wayne County
$177Delta
Sat, Sep 12 - Wed, Sep 23
Delta Logo
6:10 am - 9:17 amCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 1:28 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
2h 59m1 stop Detroit Metropolitan Wayne County
$177Delta
Mon, Sep 7 - Thu, Sep 10
Southwest Logo
7:00 am - 10:50 amCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
4h 50m1 stop Nashville Intl
Southwest Logo
7:05 am - 1:45 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
5h 40m1 stop Nashville Intl
$177Southwest
Tue, Sep 29 - Thu, Oct 1
Delta Logo
7:00 am - 12:05 pmSDF  Louisville Intl-MDW Chicago Midway
6h 05m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:19 pm - 9:32 pmMDW  Chicago Midway-SDF Louisville Intl
4h 13m1 stop Atlanta Hartsfield-Jackson
$203Delta
Thu, Nov 12 - Sat, Nov 14
Delta Logo
6:00 pm - 10:44 pmSDF  Louisville Intl-MDW Chicago Midway
5h 44m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:00 pm - 7:10 pmMDW  Chicago Midway-SDF Louisville Intl
5h 10m1 stop Atlanta Hartsfield-Jackson
$203Delta
Tue, Sep 8 - Tue, Sep 15
Allegiant Air Logo
1:58 pm - 2:37 pmTYS  Knoxville McGhee Tyson-MDW Chicago Midway
1h 39mnonstop
Allegiant Air Logo
3:27 pm - 5:54 pmMDW  Chicago Midway-TYS Knoxville McGhee Tyson
1h 27mnonstop
$321Allegiant Air
Wed, Nov 25 - Sun, Nov 29
Allegiant Air Logo
11:04 am - 11:36 amTYS  Knoxville McGhee Tyson-MDW Chicago Midway
1h 32mnonstop
Allegiant Air Logo
11:38 am - 10:23 pmMDW  Chicago Midway-TYS Knoxville McGhee Tyson
9h 45m1 stop Punta Gorda
$349Allegiant Air
Fri, Oct 9 - Sun, Oct 11

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Southwest flights from Kentucky to Chicago Midway Airport

Our best Southwest deals on Kentucky to Chicago Midway Airport flight tickets
Southwest
Sep 10
CVG2:10 pmCincinnati Cinci./N. Kentucky
6h 25m
2 stops
MDW7:35 pmChicago Midway
Sep 14
MDW8:05 amChicago Midway
1h 20m
CVG10:25 amCincinnati Cinci./N. Kentucky
$172
Southwest
Sep 11
CVG5:25 pmCincinnati Cinci./N. Kentucky
6h 00m
1 stop
MDW10:25 pmChicago Midway
Sep 17
MDW5:55 amChicago Midway
5h 20m
1 stop
CVG12:15 pmCincinnati Cinci./N. Kentucky
$176
Southwest
Sep 11
CVG5:25 pmCincinnati Cinci./N. Kentucky
3h 45m
1 stop
MDW8:10 pmChicago Midway
Sep 18
MDW8:05 amChicago Midway
1h 20m
CVG10:25 amCincinnati Cinci./N. Kentucky
$178

Frontier flights from Kentucky to Chicago Midway Airport

Our best Frontier deals on Kentucky to Chicago Midway Airport flight tickets
Frontier
Sep 8
CVG12:26 pmCincinnati Cinci./N. Kentucky
11h 21m
1 stop
MDW10:47 pmChicago Midway
Sep 10
MDW6:46 pmChicago Midway
15h 52m
1 stop
CVG11:38 amCincinnati Cinci./N. Kentucky
$188
Frontier
Oct 11
CVG5:11 pmCincinnati Cinci./N. Kentucky
7h 32m
1 stop
MDW11:43 pmChicago Midway
Oct 14
MDW1:12 pmChicago Midway
5h 58m
1 stop
CVG8:10 pmCincinnati Cinci./N. Kentucky
$194
Frontier
Sep 19
CVG12:43 pmCincinnati Cinci./N. Kentucky
6h 08m
1 stop
MDW5:51 pmChicago Midway
Sep 21
MDW6:46 pmChicago Midway
15h 52m
1 stop
CVG11:38 amCincinnati Cinci./N. Kentucky
$195

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 17, 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

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 9/12

4:55 pm-5:05 pm

Nonstop1h 10m

Chicago Midway

Wed 9/23

2:00 pm-8:55 pm

2 stops5h 55m

$172

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway

CVGMDW

Cincinnati Cinci./N. Kentucky

Wed 9/9

7:15 pm-7:25 pm

Nonstop1h 10m

Chicago Midway

Fri 9/11

2:35 pm-10:25 pm

2 stops6h 50m

$172

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway

CVGMDW

Cincinnati Cinci./N. Kentucky

Fri 9/11

5:25 pm-10:25 pm

1 stop6h 00m

Chicago Midway

Thu 9/17

5:55 am-12:15 pm

1 stop5h 20m

$176

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 9/12

11:45 am-4:57 pm

1 stop6h 12m

Chicago Midway

Wed 9/23

9:29 am-3:14 pm

1 stop4h 45m

$177

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway

CVGMDW

Cincinnati Cinci./N. Kentucky

Mon 9/7

6:10 am-9:17 am

1 stop4h 07m

Chicago Midway

Thu 9/10

9:29 am-1:28 pm

1 stop2h 59m

$177

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 9/29

7:00 am-10:50 am

1 stop4h 50m

Chicago Midway

Thu 10/1

7:05 am-1:45 pm

1 stop5h 40m

$177

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Thu 11/12

7:00 am-12:05 pm

1 stop6h 05m

Chicago Midway

Sat 11/14

4:19 pm-9:32 pm

1 stop4h 13m

$203

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Tue 9/8

6:00 pm-10:44 pm

1 stop5h 44m

Chicago Midway

Tue 9/15

1:00 pm-7:10 pm

1 stop5h 10m

$203
Quickest round-trip

KnoxvilleChicago

TYS Knoxville McGhee Tyson - MDW Chicago Midway

TYSMDW

Knoxville McGhee Tyson

Wed 11/25

1:58 pm-2:37 pm

Nonstop1h 39m

Chicago Midway

Sun 11/29

3:27 pm-5:54 pm

Nonstop1h 27m

$321

KnoxvilleChicago

TYS Knoxville McGhee Tyson - MDW Chicago Midway

TYSMDW

Knoxville McGhee Tyson

Fri 10/9

11:04 am-11:36 am

Nonstop1h 32m

Chicago Midway

Sun 10/11

11:38 am-10:23 pm

1 stop9h 45m

$349

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 $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 $394. 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, Wednesday 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 $458.

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 $411 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $450. 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 Airport flights?

There is only 1 cabin class available to choose from on Kentucky to Chicago Midway Airport 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 33% 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

$45

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 $45. The best round-trip flight deal from Kentucky to Chicago Midway Airport found on momondo in the last 72 hours is $172.
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
4,218 reviews
Search Southwest flights

Traveling to a place near Chicago?

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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.

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