Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Kentucky to Chicago Midway Airport from $59

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 Midway Airport departing on 2/19. 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
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Kentucky to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Kentucky to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Kentucky to Chicago.

Cheap last minute flights

Planning a quick getaway from Kentucky to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Kentucky to Chicago

Find recent round-trip train or bus tickets from Kentucky to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
2:45 pm - 4:20 pmBNA-MDW
1h 35mnonstop
3:15 pm - 4:45 pmMDW-BNA
1h 30mnonstop
$129Southwest
Find Deal
sáb., feb. 8 - mar., feb. 11
4:19 pm - 12:17 amTYS-MDW
8h 58m1 stop
7:15 am - 3:19 pmMDW-TYS
7h 04m1 stop
$148Frontier
Find Deal
jue., ene. 16 - jue., ene. 23
4:50 pm - 11:14 pmCVG-MDW
7h 24m1 stop
12:43 pm - 11:50 pmMDW-CVG
10h 07m1 stop
$148Frontier
Find Deal
lun., ene. 6 - jue., ene. 9
2:30 pm - 4:05 pmBNA-MDW
1h 35mnonstop
2:05 pm - 3:35 pmMDW-BNA
1h 30mnonstop
$149Southwest
Find Deal
jue., ene. 9 - sáb., ene. 11
6:00 am - 12:13 amCVG-MDW
19h 13m1 stop
7:25 am - 8:30 pmMDW-CVG
12h 05m1 stop
$153Frontier
Find Deal
jue., ene. 9 - jue., ene. 16
7:13 pm - 12:20 amBNA-MDW
5h 07m1 stop
10:27 pm - 11:33 amMDW-BNA
13h 06m1 stop
$154Frontier
Find Deal
vie., dic. 13 - mié., dic. 18
6:15 am - 1:08 pmBNA-MDW
6h 53m1 stop
2:08 pm - 9:11 pmMDW-BNA
7h 03m1 stop
$176Delta
Find Deal
mar., ene. 7 - mar., ene. 14
6:25 am - 12:50 pmBNA-MDW
6h 25m1 stop
6:00 am - 9:55 amMDW-BNA
3h 55m1 stop
$196Delta
Find Deal
mar., dic. 10 - mar., dic. 17
5:54 pm - 6:32 pmLEX-MDW
25h 38m3 stops
9:38 am - 5:14 pmMDW-LEX
30h 36m3 stops
$1,383WestJet
Find Deal
vie., dic. 13 - dom., dic. 15
5:54 pm - 6:32 pmLEX-MDW
25h 38m3 stops
2:15 pm - 5:14 pmMDW-LEX
25h 59m3 stops
$1,438WestJet
Find Deal
vie., dic. 13 - dom., dic. 15
12:00 pm - 1:35 pmBNA-MDW
1h 35mnonstop
$59Southwest
Find Deal
mié., feb. 19
2:40 pm - 4:15 pmBNA-MDW
1h 35mnonstop
$70Southwest
Find Deal
sáb., ene. 11
6:01 pm - 12:17 amBNA-MDW
6h 16m1 stop
$74Frontier
Find Deal
lun., feb. 24
4:00 pm - 10:33 pmCVG-MDW
7h 33m1 stop
$74Frontier
Find Deal
mar., dic. 24
12:00 pm - 1:35 pmBNA-MDW
1h 35mnonstop
$79Southwest
Find Deal
jue., ene. 9
6:15 am - 1:08 pmBNA-MDW
6h 53m1 stop
$88Delta
Find Deal
dom., ene. 12
7:20 am - 11:58 amLEX-MDW
5h 38m1 stop
$104Delta
Find Deal
mié., dic. 18
6:34 pm - 8:41 amBNA-MDW
14h 07m1 stop
$112Avelo Airlines
Find Deal
lun., ene. 6
9:50 pm - 7:50 amCVG-MDW
11h 00m1 stop
$140Allegiant Air
Find Deal
dom., mar. 16
9:50 pm - 7:50 amCVG-MDW
11h 00m1 stop
$148Allegiant Air
Find Deal
jue., mar. 13
1:50 pm - 2:24 pmTYS-MDW
1h 34mnonstop
6:16 pm - 8:43 pmMDW-TYS
1h 27mnonstop
$214Allegiant Air
Find Deal
lun., nov. 25 - mié., nov. 27
4:52 pm - 5:26 pmTYS-MDW
1h 34mnonstop
7:00 am - 6:15 pmMDW-TYS
10h 15m1 stop
mié., nov. 27 - vie., nov. 29
8:07 am - 11:58 amTYS-MDW
4h 51m1 stop
6:49 pm - 11:50 pmMDW-TYS
4h 01m1 stop
$353Delta
Find Deal
mié., nov. 27 - lun., dic. 2
2:24 pm - 6:02 pmTYS-MDW
4h 38m1 stop
3:19 pm - 8:26 pmMDW-TYS
4h 07m1 stop
$368Delta
Find Deal
lun., nov. 25 - jue., nov. 28
6:30 am - 1:10 pmCVG-MDW
7h 40m1 stop
12:43 pm - 11:46 pmMDW-CVG
10h 03m1 stop
$378Frontier
Find Deal
jue., nov. 28 - jue., dic. 5
4:52 pm - 5:26 pmTYS-MDW
1h 34mnonstop
8:15 pm - 3:28 pmMDW-TYS
18h 13m2 stops
$408Allegiant Air
Find Deal
mié., nov. 27 - dom., dic. 1
2:24 pm - 5:54 pmTYS-MDW
4h 30m1 stop
3:19 pm - 8:26 pmMDW-TYS
4h 07m1 stop
$473Delta
Find Deal
mar., nov. 26 - vie., nov. 29
1:35 pm - 3:10 pmBNA-MDW
1h 35mnonstop
2:50 pm - 7:45 pmMDW-BNA
4h 55m1 stop
$506Southwest
Find Deal
vie., nov. 29 - vie., dic. 6
2:15 pm - 5:15 pmBNA-MDW
3h 00m1 stop
9:55 am - 2:15 pmMDW-BNA
4h 20m1 stop
$515Southwest
Find Deal
vie., nov. 29 - vie., dic. 6
8:34 pm - 1:10 pmBNA-MDW
16h 36m1 stop
5:10 am - 8:12 pmMDW-BNA
15h 02m1 stop
$526Frontier
Find Deal
mié., nov. 27 - sáb., nov. 30
2:45 pm - 4:20 pmBNA-MDW
1h 35mnonstop
3:15 pm - 4:45 pmMDW-BNA
1h 30mnonstop
$129Southwest
Find Deal
sáb., feb. 8 - mar., feb. 11
2:30 pm - 4:05 pmBNA-MDW
1h 35mnonstop
2:05 pm - 3:35 pmMDW-BNA
1h 30mnonstop
$149Southwest
Find Deal
jue., ene. 9 - sáb., ene. 11
7:20 am - 8:55 amBNA-MDW
1h 35mnonstop
8:40 pm - 10:10 pmMDW-BNA
1h 30mnonstop
$159Southwest
Find Deal
lun., feb. 3 - mar., feb. 4
10:25 pm - 11:55 pmBNA-MDW
1h 30mnonstop
9:00 am - 10:30 amMDW-BNA
1h 30mnonstop
$178Southwest
Find Deal
dom., dic. 15 - mar., dic. 17
10:25 pm - 11:55 pmBNA-MDW
1h 30mnonstop
9:00 am - 10:30 amMDW-BNA
1h 30mnonstop
$198Southwest
Find Deal
dom., dic. 15 - mié., dic. 18
10:25 pm - 11:55 pmBNA-MDW
1h 30mnonstop
5:30 pm - 7:00 pmMDW-BNA
1h 30mnonstop
$204Southwest
Find Deal
vie., dic. 13 - mié., dic. 18
7:35 pm - 9:10 pmBNA-MDW
1h 35mnonstop
7:30 pm - 9:00 pmMDW-BNA
1h 30mnonstop
$218Southwest
Find Deal
dom., dic. 8 - mar., dic. 10
7:30 am - 9:05 amBNA-MDW
1h 35mnonstop
4:35 pm - 6:00 pmMDW-BNA
1h 25mnonstop
$224Southwest
Find Deal
mié., dic. 11 - sáb., dic. 14
6:35 pm - 6:50 pmSDF-MDW
1h 15mnonstop
7:30 pm - 9:40 pmMDW-SDF
1h 10mnonstop
$226Southwest
Find Deal
mar., dic. 24 - mar., dic. 31
10:25 pm - 11:55 pmBNA-MDW
1h 30mnonstop
1:30 pm - 2:55 pmMDW-BNA
1h 25mnonstop
$238Southwest
Find Deal
dom., dic. 8 - jue., dic. 12

Southwest flights from Kentucky to Chicago Midway Airport

Our best Southwest deals on Kentucky to Chicago Midway Airport flight tickets
Southwest
Feb 8
BNA2:45 pmNashville Intl
1h 35m
MDW4:20 pmChicago Midway
Feb 11
MDW3:15 pmChicago Midway
1h 30m
BNA4:45 pmNashville Intl
Southwest
Jan 9
BNA2:30 pmNashville Intl
1h 35m
MDW4:05 pmChicago Midway
Jan 11
MDW2:05 pmChicago Midway
1h 30m
BNA3:35 pmNashville Intl
Southwest
Feb 3
BNA7:20 amNashville Intl
1h 35m
MDW8:55 amChicago Midway
Feb 4
MDW8:40 pmChicago Midway
1h 30m
BNA10:10 pmNashville Intl

Frontier flights from Kentucky to Chicago Midway Airport

Our best Frontier deals on Kentucky to Chicago Midway Airport flight tickets
Frontier
Jan 16
TYS4:19 pmKnoxville McGhee Tyson
8h 58m
1 stop
MDW12:17 amChicago Midway
Jan 23
MDW7:15 amChicago Midway
7h 04m
1 stop
TYS3:19 pmKnoxville McGhee Tyson
Frontier
Jan 9
CVG6:00 amCincinnati Cinci./N. Kentucky
19h 13m
1 stop
MDW12:13 amChicago Midway
Jan 16
MDW7:25 amChicago Midway
12h 05m
1 stop
CVG8:30 pmCincinnati Cinci./N. Kentucky
Frontier
Dec 13
BNA7:13 pmNashville Intl
5h 07m
1 stop
MDW12:20 amChicago Midway
Dec 18
MDW10:27 pmChicago Midway
13h 06m
1 stop
BNA11:33 amNashville Intl

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 day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Kentucky. The lowest ticket price found for a Wednesday departure recently was $195. 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, Saturday 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 $321.

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 $236 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $271. 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?

You could potentially save up to 25% 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

$59

Fastest flight time

1h 00m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Kentucky in the past 72 hours is $59. The best round-trip flight deal from Kentucky to Chicago Midway Airport found on momondo in the last 72 hours is $129.
The fastest flight from Kentucky to Chicago Midway Airport takes 1h 00m
Direct flights go from Kentucky to Chicago Midway Airport every day.

  • 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
DeltaPriceFrom $135Free CancellationRating
8.0
8,735 reviews
Search Delta flights
SouthwestPriceFrom $156Free CancellationRating
8.1
4,990 reviews
Search Southwest flights

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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
sáb. 11/30
sáb. 12/7
Email me momondo's favorite deals

Find better results for your trip to Chicago