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$39+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Nov 3 — Nov 101
Mon 11/3
Mon 11/10
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Louisville Intl are usually found in August or May, booked 76 days in advance, depart on a Saturday or Thursday and return on a Thursday

Cheap 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 October 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$77
(Southwest)

One-way from

$39
(Southwest)

Popular in

February

Cheapest in

August

Average price

$284

Good round-trip deal

$129 or less

Good one-way deal

$137 or less
Provider with most accurate pricing for Chicago (CHI)-Louisville Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Louisville Intl flights.
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From Chicago (CHI) to Louisville Intl
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One-way flight from Chicago (CHI) to Louisville Intl
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Highest demand for flights based on searches. 16% potential increase in price ($61 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Louisville Intl.
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Price to beat on a one-way flight from Chicago (CHI) to Louisville Intl.
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Find 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 October 4, 2025.

This United Airlines deal was found by Cheapflights users on 10/2. 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.
Thu 10/237:25 amORD - SDF
Nonstop1h 36mUnited Airlines
Thu 10/307:00 amSDF - ORD
Nonstop1h 40mUnited Airlines
Deal found 10/2$77
This Southwest deal was found by Cheapflights users on 10/2. 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 10/279:55 amMDW - SDF
Nonstop1h 10mSouthwest
Mon 10/278:15 pmSDF - MDW
Nonstop1h 15mSouthwest
Deal found 10/2$77
This Southwest deal was found by Cheapflights users on 10/2. 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 10/3110:15 amMDW - SDF
Nonstop1h 15mSouthwest
Mon 11/37:05 pmSDF - MDW
Nonstop1h 15mSouthwest
Deal found 10/2$84
This Southwest deal was found by Cheapflights users on 10/2. 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 10/275:20 pmMDW - SDF
1 stop5h 50mSouthwest
Tue 10/286:25 amSDF - MDW
Nonstop1h 15mSouthwest
Deal found 10/2$87
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Fri 10/317:10 pmORD - SDF
Nonstop1h 35mAmerican Airlines
Mon 11/36:00 amSDF - ORD
Nonstop1h 40mAmerican Airlines
Deal found 10/2$91
This American Airlines deal was found by Cheapflights users on 10/2. 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 10/306:59 amORD - SDF
Nonstop1h 24mAmerican Airlines
Mon 11/312:43 pmSDF - ORD
Nonstop1h 38mAmerican Airlines
Deal found 10/2$92
This Southwest deal was found by Cheapflights users on 10/2. 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 10/304:35 pmMDW - SDF
2 stops6h 35mSouthwest
Mon 11/31:50 pmSDF - MDW
Nonstop1h 15mSouthwest
Deal found 10/2$92
This Southwest deal was found by Cheapflights users on 10/2. 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.
Wed 10/295:30 amMDW - SDF
1 stop7h 55mSouthwest
Wed 10/293:50 pmSDF - MDW
1 stop6h 00mSouthwest
Deal found 10/2$97
This Southwest deal was found by Cheapflights users on 10/2. 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 10/277:30 amORD - SDF
1 stop7h 30mSouthwest
Tue 10/281:45 pmSDF - ORD
1 stop8h 45mSouthwest
Deal found 10/2$102
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Thu 12/187:25 amORD - SDF
Nonstop1h 38mUnited Airlines
Wed 12/2410:50 amSDF - ORD
Nonstop1h 43mUnited Airlines
Deal found 10/2$106
This Southwest deal was found by Cheapflights users on 10/3. 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 11/412:25 pmMDW - SDF
1 stop3h 45mSouthwest
Thu 11/61:55 pmSDF - MDW
Nonstop1h 15mSouthwest
Deal found 10/3$107
This Southwest deal was found by Cheapflights users on 10/2. 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 10/231:50 pmORD - SDF
1 stop9h 20mSouthwest
Thu 10/305:40 amSDF - ORD
1 stop8h 05mSouthwest
Deal found 10/2$108

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 October 4, 2025.
Use the filters below to find and compare flights from Chicago to Louisville that are best for you.

Fly from

Chicago

Fly to

Louisville

Route

Depart

Return

Price

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Mon 11/3

8:50 pm-11:05 pm

Nonstop1h 15m

Louisville Intl

Thu 11/6

1:55 pm-2:10 pm

Nonstop1h 15m

$77

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Thu 10/30

9:55 am-12:05 pm

Nonstop1h 10m

Louisville Intl

Mon 11/3

6:45 am-7:00 am

Nonstop1h 15m

$77

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Thu 12/18

2:40 pm-4:50 pm

Nonstop1h 10m

Louisville Intl

Wed 12/24

6:45 am-7:00 am

Nonstop1h 15m

$77

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Fri 10/31

10:15 am-12:30 pm

Nonstop1h 15m

Louisville Intl

Mon 11/3

3:20 pm-9:05 pm

1 stop6h 45m

$94

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Wed 11/19

10:05 am-12:30 pm

Nonstop1h 25m

Louisville Intl

Wed 11/19

1:50 pm-2:05 pm

Nonstop1h 15m

$97

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 11/4

10:05 am-12:30 pm

Nonstop1h 25m

Louisville Intl

Thu 11/6

8:10 pm-8:30 pm

Nonstop1h 20m

$97

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Sat 11/22

9:41 am-12:13 pm

Nonstop1h 32m

Louisville Intl

Sat 11/22

5:20 pm-6:05 pm

Nonstop1h 45m

$171

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Mon 11/10

6:45 am-1:42 pm

1 stop5h 57m

Louisville Intl

Thu 11/13

7:54 pm-12:01 am

1 stop5h 07m

$177

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Thu 11/20

6:45 am-12:07 pm

1 stop4h 22m

Louisville Intl

Mon 11/24

3:09 pm-6:52 pm

1 stop4h 43m

$177

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Mon 10/27

4:56 pm-9:15 pm

1 stop3h 19m

Louisville Intl

Tue 10/28

7:09 am-4:11 pm

2 stops10h 02m

$182

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/2

Showing 1-10 of 38 results
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Louisville. Price data was last updated on September 26, 2025.

Booking 73 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 month to book a flight from Chicago to Louisville?

Currently, January is the cheapest month in which you can book a flight from Chicago to Louisville (average of $299). Flying from Chicago to Louisville in April is currently the most expensive (average of $369). 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 October 4, 2025.

It’s typically best to fly out from Chicago to Louisville in the afternoon. Doing so could potentially save you 14% on the flight price compared to flying in the morning, which is usually more expensive.

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 September 28, 2025.

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

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 October 4, 2025.

The most flights from CHI to SDF are scheduled on a Saturday (38 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (18 on average).

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

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 October 4, 2025.
Read through reviews of airlines operating flights from Chicago to Louisville, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,946 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,041 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the 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 25 daily inbound flights from Chicago from 3 different airlines.

  • How long is the flight from Chicago to Louisville?

    For as low as $77, 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 American Airlines. Our recent data shows that you can find tickets from as low as $121 on this airline. Additional options worth looking into are Southwest and United Airlines, starting at $124 and $137 round-trip. You may be able to fly from Chicago to Louisville for 59% 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: Japan Airlines (97%), Alaska Airlines (93%), Envoy Air (93%).

  • What are the cheapest flights from Chicago to Louisville?

    Looking at all options, your cheapest flight can be booked for $66. While the most popular route (Chicago O'Hare Intl - Louisville Intl) can be booked for $77 on average, our data indicates $294 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, January is the cheapest month in which you can book a flight from Chicago to Louisville (average of $299). Flying from Chicago to Louisville in April is currently the most expensive (average of $369). 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
Shepherdsville
Jeffersonville
Elizabethtown
Corydon
Bardstown

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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 October 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$121Average$285FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$124Average$556FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$137Average$300FlexibilityNo cancel feeOn-time69%

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