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

Airfare is below average for this route at the moment. Louisville to Chicago flights typically cost between $186 and $405 in September. The cheapest round-trip price found within the last 3 days was $97 on Southwest (Sep 16-Sep 16).

How long is the flight from Louisville to Chicago?

There are many flights that can get you from Louisville to Chicago in 1h 49m. Fly via Southwest or United Airlines to get the fastest option. Airlines will cover a distance of 287 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 $133 round-trip. American Airlines is currently priced 62% below the average price you’ll pay for this route.

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 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, 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 day to fly from Louisville to Chicago?

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

The most flights from SDF to CHI are scheduled on a Monday (47 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the cheapest flights from Louisville to Chicago?

Looking at all options, your cheapest flight can be booked for $69. While the most popular route (Louisville Intl - Chicago O'Hare Intl) can be booked for $97 on average our data indicates $834 when flying from Louisville to Chicago.

What are the most reliable airlines from Louisville to Chicago?

The top 3 most reliable airlines when flying from Louisville to Chicago are Royal Jordanian (91%), Japan Airlines (87%) and Copa Airlines (85%).

What is the cheapest day to fly round-trip from Louisville to Chicago?

Flights from Louisville to Chicago are found to be more expensive on Saturday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

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

To save up to 282% on this flight, we recommend booking at least 42 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Louisville to Chicago from $355 1-2 weeks out and tickets from $472 for flights departing within the next 72 hours.

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

Due to multiple factors, expect to potentially pay more when booking in March. For low rates, April can be a great choice for travel to Chicago. Flights to Chicago from Louisville in April are about $259 on average during April, but can be found for as low as $124.

What is the cheapest time of day to fly from SDF to CHI?

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 38% on airfare.

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 29 outbound flights to Chicago per day.

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.

$39+ Cheap Flights from Louisville to Chicago

Round-trip from	$97 (Southwest)
One-way from	$39 (United Airlines)
Popular in	March
Cheapest in	April
Average price	$266
Good round-trip deal	$183 or less
Good one-way deal	$147 or less

Southwest allows two free checked bags, including oversized items like skis or golf clubs.

Southwest offers free in-flight entertainment streamed to passenger devices, including movies and live TV.

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$97	Average$264	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$97	Average$264	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$133	Average$295	FlexibilityNo cancel fee	On-time69%

$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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Louisville to Chicago with Cheapflights

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

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Cheapest flights from Louisville to ChicagoExplore 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 August 19, 2025.

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 August 19, 2025.

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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.

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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 August 8, 2025.

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

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 August 19, 2025.

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 August 17, 2025.

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 August 19, 2025.

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

Reviews of airlines servicing Chicago

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.

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?

How long is the flight from Louisville to Chicago?

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

What are the most reliable airlines from Louisville to Chicago?

What are the cheapest flights from Louisville to Chicago?

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

How can I find direct flights from Louisville to Chicago?

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

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

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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 August 19, 2025.