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$39+ Cheap flights from Louisville (SDF) to Chicago (CHI)

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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
nov. 1 — nov. 81
sáb. 11/1
sáb. 11/8
1 adult, Economy
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Cheapflights Tip: The best prices from Louisville Intl to Chicago are usually found in November or April, booked 76 days in advance, depart on a Thursday or Friday and return on a Saturday

Cheap flight deals from Louisville to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Louisville (SDF) to Chicago (CHI). 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 octubre 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$137
(United Airlines)

One-way from

$39
(United Airlines)

Popular in

March

Cheapest in

November

Average price

$249

Good round-trip deal

$255 or less

Good one-way deal

$143 or less
Provider with most accurate pricing for Louisville Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Louisville Intl-Chicago (CHI) flights.
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From Louisville Intl to Chicago (CHI)
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One-way flight from Louisville Intl to Chicago (CHI)
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High demand for flights, 1% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($3 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 Louisville Intl to Chicago (CHI).
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Price to beat on a one-way flight from Louisville Intl to Chicago (CHI).
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Find flight deals from Louisville to Chicago

Cheapest flights from Louisville to Chicago
Explore the most affordable flight options available from Louisville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 2, 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.
jue. 10/237:00 amSDF - ORD
Nonstop1h 38mUnited Airlines
lun. 10/277:55 pmORD - SDF
Nonstop1h 34mUnited Airlines
Deal found 10/2$137
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/287:00 amSDF - ORD
Nonstop1h 40mUnited Airlines
mié. 10/297:30 amORD - SDF
Nonstop1h 29mUnited Airlines
Deal found 10/2$139
This American Airlines deal was found by Cheapflights users on 10/1. 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.
mié. 10/296:45 amSDF - ORD
Nonstop1h 33mAmerican Airlines
mié. 11/58:25 pmORD - SDF
Nonstop1h 30mAmerican Airlines
Deal found 10/1$145
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.
sáb. 10/254:25 pmSDF - MDW
Nonstop1h 15mSouthwest
lun. 10/279:55 amMDW - SDF
Nonstop1h 10mSouthwest
Deal found 10/2$154
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.
jue. 10/238:45 amSDF - ORD
Nonstop1h 38mUnited Airlines
sáb. 10/2510:50 amORD - SDF
Nonstop1h 31mUnited Airlines
Deal found 10/2$158
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.
jue. 10/238:15 pmSDF - MDW
Nonstop1h 15mSouthwest
lun. 10/279:55 amMDW - SDF
Nonstop1h 10mSouthwest
Deal found 10/2$158
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.
sáb. 11/157:25 amSDF - ORD
Nonstop1h 40mAmerican Airlines
jue. 11/202:14 pmORD - SDF
Nonstop1h 36mAmerican Airlines
Deal found 10/2$161
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.
jue. 10/235:40 amSDF - MDW
1 stop5h 35mSouthwest
sáb. 10/257:35 pmMDW - SDF
Nonstop1h 10mSouthwest
Deal found 10/2$164
This American Airlines deal was found by Cheapflights users on 10/1. 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.
lun. 10/275:53 pmSDF - ORD
Nonstop1h 36mAmerican Airlines
mar. 10/288:28 pmORD - SDF
Nonstop1h 35mAmerican Airlines
Deal found 10/1$165
This American Airlines deal was found by Cheapflights users on 9/30. 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.
mar. 11/119:22 amSDF - ORD
1 stop7h 34mAmerican Airlines
mar. 11/118:25 pmORD - SDF
Nonstop1h 30mAmerican Airlines
Deal found 9/30$171
This Southwest deal was found by Cheapflights users on 10/1. 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.
vie. 10/248:15 pmSDF - MDW
Nonstop1h 15mSouthwest
lun. 10/279:55 amMDW - SDF
Nonstop1h 10mSouthwest
Deal found 10/1$171
This Southwest deal was found by Cheapflights users on 10/1. 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.
lun. 10/278:15 pmSDF - MDW
Nonstop1h 15mSouthwest
mar. 10/285:45 amMDW - SDF
2 stops9h 35mSouthwest
Deal found 10/1$173

Cheapflights Fare Finder

 
Customize your flight search to find flights from Louisville to Chicago 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 octubre 2, 2025.
Use the filters below to find and compare flights from Louisville to Chicago that are best for you.

Fly from

Louisville

Fly to

Chicago

Route

Depart

Return

Price

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

jue. 10/23

7:00 am-7:38 am

Nonstop1h 38m

Chicago O'Hare Intl

lun. 10/27

7:55 pm-10:29 pm

Nonstop1h 34m

$137

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

mar. 11/11

9:00 am-9:40 am

Nonstop1h 40m

Chicago O'Hare Intl

mié. 11/12

7:30 am-9:59 am

Nonstop1h 29m

$139

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

jue. 10/23

8:15 pm-8:30 pm

Nonstop1h 15m

Chicago Midway

lun. 10/27

9:55 am-12:05 pm

Nonstop1h 10m

$158

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

sáb. 11/8

7:00 am-7:40 am

Nonstop1h 40m

Chicago O'Hare Intl

lun. 11/17

7:55 pm-10:29 pm

Nonstop1h 34m

$158

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

mar. 12/23

1:52 pm-5:22 pm

1 stop4h 30m

Chicago O'Hare Intl

mar. 12/30

7:00 am-1:12 pm

1 stop5h 12m

$177

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

mié. 10/29

8:17 am-12:16 pm

1 stop4h 59m

Chicago O'Hare Intl

mié. 11/5

5:51 pm-12:01 am

1 stop5h 10m

$177

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

mar. 12/30

1:52 pm-5:22 pm

1 stop4h 30m

Chicago O'Hare Intl

jue. 1/1

7:00 am-1:12 pm

1 stop5h 12m

$177

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mar. 11/11

6:00 am-9:52 am

1 stop4h 52m

Chicago Midway

mar. 11/11

5:34 pm-12:06 am

1 stop5h 32m

$177

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

jue. 10/23

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

mar. 10/28

5:04 pm-10:34 pm

1 stop4h 30m

$177

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mié. 10/22

5:58 pm-10:14 pm

1 stop5h 16m

Chicago Midway

jue. 10/30

9:35 am-1:53 pm

1 stop3h 18m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/1

Showing 1-10 of 42 results
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Compare providers for flights from Louisville to Chicago

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 Louisville to Chicago 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 Louisville-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Louisville-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Louisville-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Louisville-Chicago 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 Louisville-Chicago 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 Louisville to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Louisville 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 Louisville to Chicago

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

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

To ensure you get the cheapest price possible for a flight from Louisville to Chicago, you should look to book at least 41 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, August is the cheapest month in which you can book a flight from Louisville to Chicago (average of $245). Flying from Louisville to Chicago in March is currently the most expensive (average of $321). 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 SDF to CHI?

Find hourly flight availability from Louisville to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octubre 2, 2025.

One of the essential ways to save on airfare from Louisville to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 40% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Louisville to Chicago. Price data was last updated on September 28, 2025.

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

Weekly flight availability from Louisville to Chicago

Explore weekly flight availability from Louisville to Chicago. 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 octubre 2, 2025.

The most flights from SDF to CHI are scheduled on a Wednesday (38 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated octubre 2, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Louisville to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

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
8,933 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

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
11,033 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

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 Louisville to Chicago. 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 from for flights from Louisville to Chicago?

    Louisville Intl (SDF), located 5.3 mi from the city center, is the airport you fly out of when you book flights from Louisville to Chicago. 3 airlines have flights from Louisville Intl to Chicago on a regular basis. Booking flights from Louisville Intl to Chicago should not be difficult; the airport handles an average of 32 outbound flights to Chicago per day.

  • How long is the flight from Louisville to Chicago?

    There are many flights that can get you from Louisville to Chicago in 1h 15m. Fly via United Airlines, Southwest, or Delta to get the fastest option. Airlines will cover a distance of 271 mi. This flight may include one or multiple stops.

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

    Our cheapest airline available from Louisville to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $97 on this airline. Additional options worth looking into are Southwest and United Airlines, starting at $97 and $114 round-trip. American Airlines is currently priced 62% below the average price you’ll pay for this route.

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

    The top 3 most reliable airlines when flying from Louisville to Chicago are Japan Airlines (98%), Qatar Airways (97%) and Royal Jordanian (93%).

  • What are the cheapest flights from Louisville to Chicago?

    Looking at all options, your cheapest flight can be booked for $89. While the most popular route (Louisville Intl - Chicago O'Hare Intl) can be booked for $77 on average, our data indicates $969 when flying from Louisville to Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Louisville to Chicago 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 Louisville to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Louisville to Chicago (average of $245). Flying from Louisville to Chicago in March is currently the most expensive (average of $321). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top 3 airlines flying from Louisville to Chicago

Discover the top 3 airlines that operate flights from Louisville to Chicago. 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 octubre 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$97Average$259FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$254FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$114Average$284FlexibilityNo cancel feeOn-time69%

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