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$32+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Jan 1 — Jan 81
Thu 1/1
Thu 1/8
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Louisville Intl to Chicago are usually found in April or November, booked 76 days in advance, depart on a Thursday or Friday and return on a Saturday

Cheap 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 December 2, 2025.

This Southwest deal was found by Cheapflights users on 11/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:45 amSDF - MDW
Nonstop1h 15mSouthwest
Sat 2/2110:45 amMDW - SDF
Nonstop1h 20mSouthwest
Deal found 11/30$88
This United Airlines deal was found by Cheapflights users on 12/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:05 amSDF - ORD
Nonstop1h 44mUnited Airlines
Wed 1/75:50 pmORD - SDF
Nonstop1h 38mUnited Airlines
Deal found 12/1$94
This American Airlines deal was found by Cheapflights users on 12/2. 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.
Wed 12/246:27 amSDF - ORD
Nonstop1h 39mAmerican Airlines
Thu 12/251:30 pmORD - SDF
Nonstop1h 29mAmerican Airlines
Deal found 12/2$97
This Southwest deal was found by Cheapflights users on 12/1. 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.
Wed 12/315:30 amSDF - MDW
1 stop5h 40mSouthwest
Wed 1/77:55 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 12/1$154
This Delta deal was found by Cheapflights users on 11/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2410:14 amSDF - ORD
1 stop7h 07mDelta
Sat 2/215:25 amORD - SDF
1 stop4h 57mDelta
Deal found 11/30$157
This Delta deal was found by Cheapflights users on 11/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/241:52 pmSDF - MDW
1 stop4h 34mDelta
Sat 2/216:00 amMDW - SDF
1 stop4h 22mDelta
Deal found 11/30$157
This Delta deal was found by Cheapflights users on 11/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:25 amSDF - ORD
1 stop6h 29mDelta
Sat 2/212:03 pmORD - SDF
2 stops8h 55mDelta
Deal found 11/30$162
This Delta deal was found by Cheapflights users on 11/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/251:52 pmSDF - MDW
1 stop4h 34mDelta
Sat 2/211:28 pmMDW - SDF
2 stops9h 30mDelta
Deal found 11/30$162
This American Airlines deal was found by Cheapflights users on 11/30. 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.
Thu 12/256:27 amSDF - ORD
Nonstop1h 39mAmerican Airlines
Sat 2/214:05 pmORD - SDF
1 stop7h 19mAmerican Airlines
Deal found 11/30$174
This American Airlines deal was found by Cheapflights users on 12/1. 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.
Wed 12/318:00 amSDF - ORD
1 stop5h 40mAmerican Airlines
Wed 1/78:49 pmORD - SDF
Nonstop1h 30mAmerican Airlines
Deal found 12/1$175
This Kiwi.com deal was found by Cheapflights users on 11/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:05 amSDF - ORD
1 stop11h 37mMultiple Airlines
Wed 2/185:32 pmORD - SDF
1 stop20h 06mMultiple Airlines
Deal found 11/30$193
This United Airlines deal was found by Cheapflights users on 12/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:40 amSDF - ORD
Nonstop1h 44mUnited Airlines
Sun 1/45:54 pmORD - SDF
Nonstop1h 38mUnited Airlines
Deal found 12/1$196

Find 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 December 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$88
(Southwest)

One-way from

$32
(Southwest)

Popular in

March

Cheapest in

April

Average price

$275

Good round-trip deal

$326 or less

Good one-way deal

$156 or less
Provider with most accurate pricing for Louisville Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-Chicago (CHI) flights.
Search Deals
From Louisville Intl to Chicago (CHI)
Search Deals
One-way flight from Louisville Intl to Chicago (CHI)
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Louisville Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Louisville Intl to Chicago (CHI).
Search Deals

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 December 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 - MDW

SDFMDW

Louisville Intl

Sat 1/17

6:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Sun 1/18

10:00 am-12:15 pm

Nonstop1h 15m

$88

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Fri 1/16

5:35 am-6:19 am

Nonstop1h 44m

Chicago O'Hare Intl

Sun 1/18

5:50 pm-8:28 pm

Nonstop1h 38m

$94

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Thu 12/25

5:40 am-6:24 am

Nonstop1h 44m

Chicago O'Hare Intl

Sat 2/21

7:40 pm-10:13 pm

Nonstop1h 33m

$97

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Sat 1/17

5:35 am-6:19 am

Nonstop1h 44m

Chicago O'Hare Intl

Sun 1/18

3:00 pm-5:37 pm

Nonstop1h 37m

$97

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 2/14

6:40 am-7:05 am

Nonstop1h 25m

Chicago Midway

Sat 2/21

2:10 pm-9:35 pm

2 stops6h 25m

$112

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Fri 2/6

8:29 am-9:13 am

Nonstop1h 44m

Chicago O'Hare Intl

Sun 2/8

7:45 am-10:23 am

Nonstop1h 38m

$118

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Wed 2/18

9:00 am-9:44 am

Nonstop1h 44m

Chicago O'Hare Intl

Thu 2/19

7:40 pm-10:13 pm

Nonstop1h 33m

$151

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 12/31

5:30 am-10:10 am

1 stop5h 40m

Chicago Midway

Wed 1/7

7:55 pm-10:10 pm

Nonstop1h 15m

$154

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Sat 1/17

6:23 am-11:47 am

1 stop6h 24m

Chicago O'Hare Intl

Sun 1/18

5:30 am-11:37 am

1 stop5h 07m

$157

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Fri 1/16

4:56 pm-9:43 pm

1 stop5h 47m

Chicago O'Hare Intl

Sun 1/18

5:30 am-11:37 am

1 stop5h 07m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 39 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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Louisville-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 November 28, 2025.

To ensure you get the cheapest price possible for a flight from Louisville to Chicago, you should look to book at least 75 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, January is the cheapest month in which you can book a flight from Louisville to Chicago (average of $73). Flying from Louisville to Chicago in July is currently the most expensive (average of $139). 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 December 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 30% 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 November 29, 2025.

Travelers seeking maximum savings on their Louisville to Chicago flight should consider departing on Friday afternoons when fares are most often at their lowest. Saturday evenings 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 December 2, 2025.

The most flights from SDF to CHI are scheduled on a Tuesday (41 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 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 December 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
4,253 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,063 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
American Airlines
7.2
Good
11,045 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 24 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 25m. Fly via Southwest or United Airlines to get the fastest option. Airlines will cover a distance of 271 mi. All flights are typically nonstop.

  • 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 61% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Louisville to Chicago one-way?

    The cheapest airlines for a one-way flight from Louisville to Chicago are Southwest ($38), American Airlines ($48), and United Airlines ($54).

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

    The top 3 most reliable airlines when flying from Louisville to Chicago are Copa Airlines (85%), Japan Airlines (82%) and Envoy Air (81%).

  • What are the cheapest flights from Louisville to Chicago?

    Looking at all options, your cheapest flight can be booked for $48. While the most popular route (Louisville Intl - Chicago O'Hare Intl) can be booked for $91 on average, our data indicates $1,079 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, January is the cheapest month in which you can book a flight from Louisville to Chicago (average of $73). Flying from Louisville to Chicago in July is currently the most expensive (average of $139). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$97Average$275FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$254FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$114Average$275FlexibilityNo cancel feeOn-time69%

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