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$88+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
May 22 — May 291
Fri 5/22
Fri 5/29
1 adult, Economy
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Cheapflights Tip: The best prices from Louisville Intl to Chicago are usually found in November or October, booked 75 days in advance, depart on a Friday or Thursday and return on a Wednesday

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 April 22, 2026.

This Southwest deal was found by Cheapflights users on 4/20. 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 5/203:30 pm
SDF
-
MDW
Nonstop1h 15m
Southwest
Wed 5/277:40 am
MDW
-
SDF
Nonstop1h 10m
Southwest
Deal found 4/20$177
This Southwest deal was found by Cheapflights users on 4/19. 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 5/198:55 am
SDF
-
MDW
Nonstop1h 20m
Southwest
Tue 5/2612:50 pm
MDW
-
SDF
Nonstop1h 15m
Southwest
Deal found 4/19$178
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
Fri 5/810:33 am
SDF
-
ORD
1 stop14h 26m
Multiple Airlines
Sun 5/103:44 pm
ORD
-
SDF
1 stop16h 44m
Multiple Airlines
Deal found 4/19$191
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Fri 5/1510:33 am
SDF
-
ORD
1 stop14h 26m
Multiple Airlines
Tue 5/191:18 pm
ORD
-
SDF
1 stop21h 16m
Multiple Airlines
Deal found 4/18$199
This Delta deal was found by Cheapflights users on 4/20. 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 5/206:00 am
SDF
-
MDW
1 stop5h 00m
Delta
Wed 5/279:22 am
MDW
-
SDF
2 stops9h 28m
Delta
Deal found 4/20$202
This Southwest deal was found by Cheapflights users on 4/20. 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 5/207:00 am
SDF
-
ORD
1 stop6h 50m
Southwest
Wed 5/272:40 pm
ORD
-
SDF
1 stop5h 25m
Southwest
Deal found 4/20$209
This United Airlines deal was found by Cheapflights users on 4/21. 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 5/202:45 pm
SDF
-
ORD
Nonstop1h 41m
United Airlines
Sat 5/239:20 pm
ORD
-
SDF
Nonstop1h 29m
United Airlines
Deal found 4/21$210
This Southwest deal was found by Cheapflights users on 4/21. 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 5/203:30 pm
SDF
-
MDW
Nonstop1h 15m
Southwest
Sat 5/237:50 am
MDW
-
SDF
Nonstop1h 15m
Southwest
Deal found 4/21$210
This Southwest deal was found by Cheapflights users on 4/19. 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 5/197:00 am
SDF
-
ORD
1 stop6h 50m
Southwest
Tue 5/262:40 pm
ORD
-
SDF
1 stop5h 25m
Southwest
Deal found 4/19$215
This American Airlines deal was found by Cheapflights users on 4/21. 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 5/208:36 am
SDF
-
ORD
Nonstop1h 45m
American Airlines
Sat 5/236:47 pm
ORD
-
SDF
1 stop4h 41m
American Airlines
Deal found 4/21$220
This Southwest deal was found by Cheapflights users on 4/21. 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 5/234:50 pm
SDF
-
MDW
Nonstop1h 20m
Southwest
Tue 5/269:50 am
MDW
-
SDF
1 stop3h 55m
Southwest
Deal found 4/21$220
This Delta deal was found by Cheapflights users on 4/20. 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 5/202:34 pm
SDF
-
ORD
1 stop6h 40m
Delta
Sat 5/236:24 am
ORD
-
SDF
1 stop4h 35m
Delta
Deal found 4/20$230

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 April 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$177
(Southwest)

One-way from

$88
(Kiwi.com)

Popular in

January

Cheapest in

November

Average price

$332

Good round-trip deal

$387 or less

Good one-way deal

$219 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
Highest demand for flights based on searches. 15% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 April 22, 2026.
Use the filters below to find and compare flights from Louisville to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 5/19

7:15 pm-7:30 pm

Nonstop1h 15m

Chicago Midway

Tue 5/26

10:15 am-9:05 pm

2 stops9h 50m

$193

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 5/20

6:20 am-10:40 am

1 stop5h 20m

Chicago Midway

Wed 5/27

10:15 am-9:05 pm

2 stops9h 50m

$249

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Tue 5/19

7:00 am-12:50 pm

1 stop6h 50m

Chicago O'Hare Intl

Sat 5/23

1:55 pm-8:50 pm

1 stop5h 55m

$270

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Wed 5/20

7:15 am-7:55 am

Nonstop1h 40m

Chicago O'Hare Intl

Wed 5/27

7:00 am-9:27 am

Nonstop1h 27m

$273

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Tue 6/2

7:50 am-10:29 am

1 stop3h 39m

Chicago O'Hare Intl

Tue 6/9

5:57 pm-11:54 pm

1 stop4h 57m

$277

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 5/19

10:39 am-5:56 pm

2 stops8h 17m

Chicago Midway

Tue 5/26

9:22 am-1:51 pm

1 stop3h 29m

$282

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sun 6/7

2:30 pm-2:45 pm

Nonstop1h 15m

Chicago Midway

Wed 6/10

7:45 am-10:05 am

Nonstop1h 20m

$295

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Thu 6/18

10:02 am-10:38 am

Nonstop1h 36m

Chicago O'Hare Intl

Tue 6/23

7:52 pm-10:30 pm

Nonstop1h 38m

$297

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Tue 5/19

7:50 am-1:01 pm

1 stop6h 11m

Chicago O'Hare Intl

Sun 5/24

7:00 am-2:42 pm

2 stops6h 42m

$298
Quickest round-trip

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Fri 6/5

3:35 pm-3:50 pm

Nonstop1h 15m

Chicago Midway

Sun 6/7

8:00 am-10:15 am

Nonstop1h 15m

$301

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 40 resultsSorted by cheapest first
1
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4

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 April.
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 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 April 17, 2026.

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 $67). Flying from Louisville to Chicago in February is currently the most expensive (average of $177). 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 April 22, 2026.

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 31% 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 April 18, 2026.

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 at noon 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 April 22, 2026.

The most flights from SDF to CHI are scheduled on a Monday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 on average).

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

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 April 22, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican 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
4,330 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,330 reviews
Southwest
8.0
Very good
4,330 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,624 reviews
Southwest
8.0
Very good
4,330 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,647 reviews
Southwest
8.0
Very good
4,330 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 42 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 Southwest, United Airlines, 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 Southwest. Our recent data shows that you can find tickets from as low as $77 on this airline. Additional options worth looking into are American Airlines and United Airlines, starting at $97 and $114 round-trip. Southwest is currently priced 72% 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 Copa Airlines (80%), Qatar Airways (80%) and Republic Airways (78%).

  • What are the cheapest flights from Louisville to Chicago?

    Looking at all options, your cheapest flight can be booked for $157. While the most popular route (Louisville Intl - Chicago O'Hare Intl) can be booked for $210 on average, our data indicates $1,077 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 $67). Flying from Louisville to Chicago in February is currently the most expensive (average of $177). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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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 April 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$77Average$225FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$97Average$253FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$114Average$273FlexibilityNo cancel feeOn-time69%

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