Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Kentucky to Chicago from $99

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
3:35 pm - 3:50 pmSDF  Louisville Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
4:15 pm - 6:30 pmMDW  Chicago Midway-SDF Louisville Intl
1h 15mnonstop
$197Southwest
Mon, Oct 19 - Sat, Oct 24
Southwest Logo
5:00 pm - 5:25 pmSDF  Louisville Intl-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
6:15 pm - 8:35 pmMDW  Chicago Midway-SDF Louisville Intl
1h 20mnonstop
$197Southwest
Sat, Nov 7 - Wed, Nov 11
Southwest Logo
5:00 pm - 5:25 pmSDF  Louisville Intl-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
12:50 pm - 3:05 pmMDW  Chicago Midway-SDF Louisville Intl
1h 15mnonstop
$197Southwest
Sat, Nov 7 - Mon, Nov 9
Southwest Logo
2:05 pm - 2:20 pmSDF  Louisville Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
7:55 am - 10:10 amMDW  Chicago Midway-SDF Louisville Intl
1h 15mnonstop
$197Southwest
Tue, Oct 27 - Thu, Oct 29
Southwest Logo
7:50 pm - 8:05 pmSDF  Louisville Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
6:55 pm - 9:10 pmMDW  Chicago Midway-SDF Louisville Intl
1h 15mnonstop
$197Southwest
Thu, Oct 22 - Mon, Oct 26
Southwest Logo
6:35 pm - 7:00 pmSDF  Louisville Intl-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
3:35 pm - 5:45 pmMDW  Chicago Midway-SDF Louisville Intl
1h 10mnonstop
$197Southwest
Thu, Feb 4 - Sat, Feb 6
Southwest Logo
3:35 pm - 3:50 pmSDF  Louisville Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
12:45 pm - 3:00 pmMDW  Chicago Midway-SDF Louisville Intl
1h 15mnonstop
$197Southwest
Thu, Oct 22 - Mon, Oct 26
Southwest Logo
3:35 pm - 3:50 pmSDF  Louisville Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
6:55 pm - 9:10 pmMDW  Chicago Midway-SDF Louisville Intl
1h 15mnonstop
$197Southwest
Mon, Oct 19 - Mon, Oct 19
Delta Logo
1:01 pm - 4:18 pmSDF  Louisville Intl-MDW Chicago Midway
4h 17m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:13 pm - 11:13 pmMDW  Chicago Midway-SDF Louisville Intl
6h 00m1 stop Atlanta Hartsfield-Jackson
$217Delta
Tue, Nov 10 - Sat, Nov 14
Delta Logo
6:00 am - 10:03 amSDF  Louisville Intl-MDW Chicago Midway
5h 03m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:29 am - 4:51 pmMDW  Chicago Midway-SDF Louisville Intl
6h 22m1 stop Detroit Metropolitan Wayne County
$217Delta
Wed, Oct 21 - Sat, Oct 24

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.
Search flight deals

Delta flights from Kentucky to Chicago Midway Airport

Our best Delta deals on Kentucky to Chicago Midway Airport flight tickets
Delta
Nov 12
SDF5:59 pmLouisville Intl
5h 55m
1 stop
MDW10:54 pmChicago Midway
Nov 14
MDW11:27 amChicago Midway
4h 27m
1 stop
SDF4:54 pmLouisville Intl
$217
Delta
Oct 30
SDF2:36 pmLouisville Intl
4h 24m
1 stop
MDW6:00 pmChicago Midway
Nov 2
MDW11:38 amChicago Midway
6h 32m
1 stop
SDF7:10 pmLouisville Intl
$234
Delta
Oct 22
SDF7:55 amLouisville Intl
5h 52m
1 stop
MDW12:47 pmChicago Midway
Oct 24
MDW4:19 pmChicago Midway
4h 19m
1 stop
SDF9:38 pmLouisville Intl
$278

Southwest flights from Kentucky to Chicago Midway Airport

Our best Southwest deals on Kentucky to Chicago Midway Airport flight tickets
Southwest
Oct 22
SDF3:35 pmLouisville Intl
1h 15m
MDW3:50 pmChicago Midway
Oct 26
MDW12:45 pmChicago Midway
1h 15m
SDF3:00 pmLouisville Intl
$197
Southwest
Oct 22
SDF5:35 amLouisville Intl
4h 10m
1 stop
MDW8:45 amChicago Midway
Oct 26
MDW12:45 pmChicago Midway
1h 15m
SDF3:00 pmLouisville Intl
$207
Southwest
Oct 26
SDF8:20 amLouisville Intl
1h 15m
MDW8:35 amChicago Midway
Oct 28
MDW9:40 amChicago Midway
9h 55m
2 stops
SDF8:35 pmLouisville Intl
$212

momondo Fare Finder

 
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

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Mon 10/19

3:35 pm-3:50 pm

Nonstop1h 15m

Chicago Midway

Sat 10/24

4:15 pm-6:30 pm

Nonstop1h 15m

$197

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Sat 11/7

5:00 pm-5:25 pm

Nonstop1h 25m

Chicago Midway

Wed 11/11

6:15 pm-8:35 pm

Nonstop1h 20m

$197

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Sat 11/7

5:00 pm-5:25 pm

Nonstop1h 25m

Chicago Midway

Mon 11/9

12:50 pm-3:05 pm

Nonstop1h 15m

$197

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Tue 10/27

2:05 pm-2:20 pm

Nonstop1h 15m

Chicago Midway

Thu 10/29

7:55 am-10:10 am

Nonstop1h 15m

$197

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Thu 10/22

7:50 pm-8:05 pm

Nonstop1h 15m

Chicago Midway

Mon 10/26

6:55 pm-9:10 pm

Nonstop1h 15m

$197

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Thu 2/4

6:35 pm-7:00 pm

Nonstop1h 25m

Chicago Midway

Sat 2/6

3:35 pm-5:45 pm

Nonstop1h 10m

$197

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Thu 10/22

3:35 pm-3:50 pm

Nonstop1h 15m

Chicago Midway

Mon 10/26

12:45 pm-3:00 pm

Nonstop1h 15m

$197

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Mon 10/19

3:35 pm-3:50 pm

Nonstop1h 15m

Chicago Midway

Mon 10/19

6:55 pm-9:10 pm

Nonstop1h 15m

$197

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Tue 11/10

1:01 pm-4:18 pm

1 stop4h 17m

Chicago Midway

Sat 11/14

4:13 pm-11:13 pm

1 stop6h 00m

$217

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Wed 10/21

6:00 am-10:03 am

1 stop5h 03m

Chicago Midway

Sat 10/24

9:29 am-4:51 pm

1 stop6h 22m

$217

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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, Friday is the cheapest day to fly to Chicago Midway Airport from Kentucky. The lowest ticket price found for a Friday departure recently was $428. 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 $472.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $421 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $460. 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 20% 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

$99

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 $99. The best round-trip flight deal from Kentucky to Chicago Midway Airport found on momondo in the last 72 hours is $197.
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

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 $187Free CancellationRating
7.9
4,214 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 11/2
Mon 11/9
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago