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$89+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Jul 12 — Jul 191
Sun 7/12
Sun 7/19
1 adult, Economy
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Cheapflights Tip: The best prices from Louisville Intl to Chicago are usually found in November or December, 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 June 12, 2026.

This United Airlines deal was found by Cheapflights users on 6/9. 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.
Tue 8/45:50 pm
SDF
-
ORD
Nonstop1h 50m
United Airlines
Tue 8/114:30 pm
ORD
-
SDF
Nonstop1h 37m
United Airlines
Deal found 6/9$177
This Southwest deal was found by Cheapflights users on 6/8. 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 8/261:15 pm
SDF
-
MDW
Nonstop1h 15m
Southwest
Wed 8/266:20 pm
MDW
-
SDF
Nonstop1h 15m
Southwest
Deal found 6/8$177
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Mon 10/199:04 am
SDF
-
ORD
Nonstop1h 41m
United Airlines
Tue 10/279:30 pm
ORD
-
SDF
Nonstop1h 35m
United Airlines
Deal found 6/10$196
This Southwest deal was found by Cheapflights users on 6/8. 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 8/266:45 pm
SDF
-
MDW
Nonstop1h 15m
Southwest
Sat 8/297:50 am
MDW
-
SDF
Nonstop1h 20m
Southwest
Deal found 6/8$196
This Delta deal was found by Cheapflights users on 6/9. 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.
Tue 8/42:34 pm
SDF
-
ORD
1 stop6h 56m
Delta
Tue 8/117:00 am
ORD
-
SDF
1 stop5h 51m
Delta
Deal found 6/9$197
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Fri 9/187:10 am
SDF
-
ORD
Nonstop1h 40m
United Airlines
Tue 9/228:30 pm
ORD
-
SDF
Nonstop1h 38m
United Airlines
Deal found 6/8$214
This United Airlines deal was found by Cheapflights users on 6/10. 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 8/209:00 am
SDF
-
ORD
Nonstop1h 41m
United Airlines
Mon 8/249:25 pm
ORD
-
SDF
Nonstop1h 34m
United Airlines
Deal found 6/10$215
This Southwest deal was found by Cheapflights users on 6/8. 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 9/107:10 pm
SDF
-
MDW
Nonstop1h 15m
Southwest
Mon 9/148:00 am
MDW
-
SDF
Nonstop1h 25m
Southwest
Deal found 6/8$215
This Delta deal was found by Cheapflights users on 6/10. 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.
Mon 10/1910:15 am
SDF
-
ORD
1 stop3h 22m
Delta
Wed 10/288:55 am
ORD
-
SDF
1 stop3h 44m
Delta
Deal found 6/10$216
This Delta deal was found by Cheapflights users on 6/8. 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.
Sat 8/87:55 am
SDF
-
MDW
1 stop5h 44m
Delta
Wed 8/129:24 am
MDW
-
SDF
1 stop3h 27m
Delta
Deal found 6/8$216
This Southwest deal was found by Cheapflights users on 6/11. 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 9/27:05 am
SDF
-
MDW
2 stops9h 20m
Southwest
Mon 9/78:00 am
MDW
-
SDF
Nonstop1h 25m
Southwest
Deal found 6/11$226
This American Airlines deal was found by Cheapflights users on 6/9. 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 9/115:59 pm
SDF
-
ORD
Nonstop1h 55m
American Airlines
Mon 9/147:59 pm
ORD
-
SDF
Nonstop1h 34m
American Airlines
Deal found 6/9$233

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 June 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$177
(United Airlines)

One-way from

$89
(American Airlines)

Popular in

January

Cheapest in

November

Average price

$356

Good round-trip deal

$385 or less

Good one-way deal

$203 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. 7% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 12, 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

Thu 10/22

10:15 am-12:33 pm

1 stop3h 18m

Chicago Midway

Sat 10/24

1:00 pm-5:40 pm

1 stop3h 40m

$235

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 7/4

5:00 pm-5:15 pm

Nonstop1h 15m

Chicago Midway

Wed 7/8

7:45 am-10:05 am

Nonstop1h 20m

$276

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 8/27

2:15 pm-2:30 pm

Nonstop1h 15m

Chicago Midway

Sun 8/30

8:50 am-5:45 pm

2 stops7h 55m

$280

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Fri 8/28

7:10 am-7:50 am

Nonstop1h 40m

Chicago O'Hare Intl

Sun 8/30

10:35 am-1:11 pm

Nonstop1h 36m

$283

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 8/25

10:50 am-4:35 pm

1 stop6h 45m

Chicago Midway

Tue 8/25

6:20 pm-8:35 pm

Nonstop1h 15m

$285

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 6/30

7:49 am-12:46 pm

1 stop5h 57m

Chicago Midway

Wed 7/1

9:17 am-1:39 pm

1 stop3h 22m

$295

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 7/7

7:25 am-3:10 pm

2 stops8h 45m

Chicago Midway

Tue 7/14

9:30 am-5:10 pm

1 stop6h 40m

$301
Quickest round-trip

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sun 9/13

7:25 pm-7:40 pm

Nonstop1h 15m

Chicago Midway

Fri 9/18

12:10 pm-2:25 pm

Nonstop1h 15m

$301

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 7/21

5:25 pm-9:10 pm

1 stop4h 45m

Chicago Midway

Fri 7/24

12:45 pm-2:55 pm

Nonstop1h 10m

$305

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Fri 7/3

10:45 am-4:35 pm

2 stops6h 50m

Chicago Midway

Sat 7/18

11:30 am-1:40 pm

Nonstop1h 10m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 42 resultsSorted by cheapest first
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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 June.
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

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 June is currently the most expensive (average of $246). 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 June 12, 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 32% on airfare.

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 June 12, 2026.

The most flights from SDF to CHI are scheduled on a Wednesday (43 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).

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

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

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 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 June 8, 2026.

Travelers seeking maximum savings on their Louisville to Chicago flight should consider departing on Saturday 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.

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 June 12, 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
7.9
Good
4,234 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

7.9

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
Southwest
7.9
Good
4,234 reviews
Southwest
7.9
Good
4,234 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

7.9

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
United Airlines
7.4
Good
9,810 reviews
Southwest
7.9
Good
4,234 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

7.9

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
American Airlines
7.1
Good
11,644 reviews
Southwest
7.9
Good
4,234 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

7.9

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

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 37 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 Delta, Southwest, or United Airlines 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 $137 round-trip. Southwest is currently priced 74% 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 Iberia (85%), British Airways (83%) and Republic Airways (83%).

  • What are the cheapest flights from Louisville to Chicago?

    Looking at all options, your cheapest flight can be booked for $164. While the most popular route (Louisville Intl - Chicago O'Hare Intl) can be booked for $196 on average, our data indicates $942 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 June is currently the most expensive (average of $246). 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

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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 June 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$77Average$248FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$97Average$276FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$137Average$318FlexibilityNo cancel feeOn-time69%

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