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$105+ Cheap flights from Chicago (CHI) to Louisville (SDF)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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Cheap flight deals from Chicago to Louisville

Cheapest flights from Chicago to Louisville
Explore the most affordable flight options available from Chicago to Louisville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 27, 2026.

This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:15 am
ORD
-
SDF
Nonstop1h 28m
American Airlines
Thu 9/175:59 pm
SDF
-
ORD
Nonstop1h 55m
American Airlines
Deal found 7/27$216
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/81:00 pm
MDW
-
SDF
Nonstop1h 15m
Southwest
Tue 9/151:15 pm
SDF
-
MDW
Nonstop1h 15m
Southwest
Deal found 7/27$217
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:05 am
ORD
-
SDF
Nonstop1h 30m
American Airlines
Thu 9/1010:29 am
SDF
-
ORD
Nonstop1h 38m
American Airlines
Deal found 7/27$217
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:10 am
ORD
-
SDF
Nonstop1h 34m
American Airlines
Wed 9/1610:29 am
SDF
-
ORD
Nonstop1h 38m
American Airlines
Deal found 7/26$218
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/83:24 pm
ORD
-
SDF
Nonstop1h 36m
American Airlines
Tue 9/155:59 pm
SDF
-
ORD
Nonstop1h 55m
American Airlines
Deal found 7/24$219
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:00 am
MDW
-
SDF
Nonstop1h 25m
Southwest
Sun 9/610:00 am
SDF
-
MDW
Nonstop1h 10m
Southwest
Deal found 7/26$222
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:56 am
ORD
-
SDF
Nonstop1h 42m
United Airlines
Sun 9/67:10 am
SDF
-
ORD
Nonstop1h 40m
United Airlines
Deal found 7/23$222
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:15 pm
MDW
-
SDF
Nonstop1h 15m
Southwest
Mon 9/217:10 pm
SDF
-
MDW
Nonstop1h 15m
Southwest
Deal found 7/25$226
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:59 pm
ORD
-
SDF
Nonstop1h 34m
American Airlines
Wed 9/1610:29 am
SDF
-
ORD
Nonstop1h 38m
American Airlines
Deal found 7/26$227
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/148:00 am
MDW
-
SDF
Nonstop1h 25m
Southwest
Wed 8/195:30 am
SDF
-
MDW
1 stop4h 30m
Southwest
Deal found 7/22$237
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:55 pm
ORD
-
SDF
1 stop6h 21m
Delta
Wed 9/1610:32 am
SDF
-
ORD
1 stop6h 41m
Delta
Deal found 7/26$237
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/78:00 am
MDW
-
SDF
Nonstop1h 25m
Southwest
Mon 9/143:20 pm
SDF
-
MDW
2 stops7h 40m
Southwest
Deal found 7/24$241

Find flight deals from Chicago to Louisville

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Louisville (SDF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(American Airlines)

One-way from

$105
(Kiwi.com)

Popular in

May

Cheapest in

December

Average price

$470

Good round-trip deal

$281 or less

Good one-way deal

$179 or less
Provider with most accurate pricing for Chicago (CHI)-Louisville Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Louisville Intl flights.
Search Deals
From Chicago (CHI) to Louisville Intl
Search Deals
One-way flight from Chicago (CHI) to Louisville Intl
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($103 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Louisville Intl.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Louisville Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Louisville 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, Cheapflights users made 2,558,603 searches. Data last updated July 27, 2026.
Use the filters below to find and compare flights from Chicago to Louisville that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Thu 8/20

6:10 pm-8:25 pm

Nonstop1h 15m

Louisville Intl

Mon 8/24

2:15 pm-2:30 pm

Nonstop1h 15m

$217

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Wed 9/16

7:15 am-9:54 am

Nonstop1h 39m

Louisville Intl

Wed 9/23

7:10 am-7:50 am

Nonstop1h 40m

$217

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Sat 8/15

7:50 am-10:10 am

Nonstop1h 20m

Louisville Intl

Mon 8/17

8:30 am-2:05 pm

1 stop6h 35m

$227

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Thu 11/12

7:05 am-9:43 am

Nonstop1h 38m

Louisville Intl

Sun 11/15

9:00 am-9:43 am

Nonstop1h 43m

$227

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 9/8

1:00 pm-3:15 pm

Nonstop1h 15m

Louisville Intl

Tue 9/15

5:30 am-11:35 am

1 stop7h 05m

$227

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Thu 10/22

7:55 am-10:10 am

Nonstop1h 15m

Louisville Intl

Fri 10/23

7:50 pm-8:05 pm

Nonstop1h 15m

$227

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Wed 8/19

9:25 am-8:35 pm

2 stops10h 10m

Louisville Intl

Wed 8/26

6:45 pm-7:00 pm

Nonstop1h 15m

$232

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Wed 9/9

12:45 pm-9:35 pm

2 stops7h 50m

Louisville Intl

Wed 9/16

1:15 pm-1:30 pm

Nonstop1h 15m

$232

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Mon 9/7

8:00 am-10:25 am

Nonstop1h 25m

Louisville Intl

Mon 9/14

3:20 pm-10:00 pm

2 stops7h 40m

$232

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 9/15

1:55 pm-9:16 pm

1 stop6h 21m

Louisville Intl

Wed 9/16

2:47 pm-8:30 pm

1 stop6h 43m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

Showing 1-10 of 45 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Louisville

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Louisville in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Louisville flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Louisville flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Louisville flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Louisville flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Louisville flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Louisville

Have a flexible travel schedule? Discover the best time to fly to Louisville from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Louisville

What is the cheapest month to book a flight from Chicago to Louisville?

Currently, December is the cheapest month in which you can book a flight from Chicago to Louisville (average of $257). Flying from Chicago to Louisville in June is currently the most expensive (average of $506). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to SDF?

Find hourly flight availability from Chicago to Louisville. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 27, 2026.

It’s typically best to fly out from Chicago to Louisville in the morning. Doing so could potentially save you 20% on the flight price compared to flying in the afternoon, which is usually more expensive.

Weekly flight availability from Chicago to Louisville

Explore weekly flight availability from Chicago to Louisville. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 27, 2026.

The most flights from CHI to SDF are scheduled on a Monday (39 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (33 on average).

How much does it cost to fly round-trip from Chicago to Louisville?

Airfare is below average for this route at the moment.
Chicago to Louisville flights typically cost between $251 and $315 in August.
The cheapest round-trip price found within the last 5 days was $217 on American Airlines (Aug 15-Aug 17).

How far ahead should I book a flight from Chicago to Louisville?

Booking 82 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Louisville. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest day to fly from Chicago to Louisville?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Louisville. Price data was last updated on July 25, 2026.

Travelers seeking maximum savings on their Chicago to Louisville flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Louisville

Get insights into the airlines that provide service to Louisville. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Louisville. Reviews last updated July 27, 2026.
Read through reviews of airlines operating flights from Chicago to Louisville, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,228 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,228 reviews
Southwest
8.0
Very good
4,228 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
10,042 reviews
Southwest
8.0
Very good
4,228 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.1
Good
11,837 reviews
Southwest
8.0
Very good
4,228 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Louisville. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Louisville from Chicago?

    Located just 5.3 mi from the city center, Louisville Intl is the airport most travelers will use when flying to Louisville from Chicago. Booking flights from Chicago to Louisville Intl (SDF) should be relatively easy as there are 36 daily inbound flights from Chicago from 3 different airlines.

  • How long is the flight from Chicago to Louisville?

    For as low as $217, Southwest can have you in Louisville from Chicago in 1h 15m. The distance from Chicago to Louisville is about 271 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago to Louisville round-trip?

    Our cheapest airline available from Chicago to Louisville is Southwest. Our recent data shows that you can find tickets from as low as $129 on this airline. Additional options worth looking into are United Airlines and American Airlines, starting at $137 and $139 round-trip. You may be able to fly from Chicago to Louisville for 65% less than the average price by searching for these airlines.

  • What are the most reliable airlines from Chicago to Louisville?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Louisville on time: Alaska Airlines (79%), GoJet (77%), Japan Airlines (77%).

  • What are the cheapest flights from Chicago to Louisville?

    Looking at all options, your cheapest flight can be booked for $111. While the most popular route (Chicago O'Hare Intl - Louisville Intl) can be booked for $217 on average, our data indicates $335 when flying from Chicago to Louisville.

  • Can I find deals for flights from Chicago to Louisville that include hotel bookings?

    Yes. In addition to deals on Chicago to Louisville flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Louisville?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Louisville.

  • Can I find deals for business class flights from Chicago to Louisville?

    Yes. Cheapflights offers flight deals from Chicago to Louisville by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Louisville?

    Currently, December is the cheapest month in which you can book a flight from Chicago to Louisville (average of $257). Flying from Chicago to Louisville in June is currently the most expensive (average of $506). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Louisville?

Book flights to Louisville if you plan to visit one of these locations
Corydon
Shepherdsville
Elizabethtown
Jeffersonville
Bardstown

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Chicago to Louisville

Discover the top 3 airlines that operate flights from Chicago to Louisville. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$129Average$360FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$137Average$456FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$139Average$356FlexibilityNo cancel feeOn-time71%

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