$138 Cheap Flights from Louisville (SDF) to Chicago (ORD)

View $138 flight on Sun, May 24, 2026Opens in a new window

Popular airlines from Louisville Intl. Airport (SDF) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Louisville to Chicago (SDF-ORD)

Prices were available within the past 7 days and start at $138 for one-way flights and $275 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sun, May 24 - Wed, May 27
SDF
Louisville
ORD
Chicago
$275 Roundtrip, found 1 hour ago
$275
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sun, May 24 from Louisville to Chicago, returning Wed, May 27, priced at $275 found 1 hour ago
United
Sun, May 24 - Wed, May 27
SDF
Louisville
ORD
Chicago
$275 Roundtrip, found 1 hour ago
$275
Roundtrip
found 1 hour ago
Select United flight, departing Sun, May 24 from Louisville to Chicago, returning Wed, May 27, priced at $275 found 1 hour ago
United
Wed, May 27 - Wed, Jun 3
SDF
Louisville
ORD
Chicago
$276 Roundtrip, found 8 hours ago
$276
Roundtrip
found 8 hours ago
Select United flight, departing Wed, May 27 from Louisville to Chicago, returning Wed, Jun 3, priced at $276 found 8 hours ago
United
Wed, Jul 1 - Tue, Jul 7
SDF
Louisville
ORD
Chicago
$285 Roundtrip, found 3 hours ago
$285
Roundtrip
found 3 hours ago
Select United flight, departing Wed, Jul 1 from Louisville to Chicago, returning Tue, Jul 7, priced at $285 found 3 hours ago
American Airlines
Sun, May 24 - Wed, May 27
SDF
Louisville
ORD
Chicago
$285 Roundtrip, found 1 hour ago
$285
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sun, May 24 from Louisville to Chicago, returning Wed, May 27, priced at $285 found 1 hour ago
United
Sun, May 24 - Wed, May 27
SDF
Louisville
ORD
Chicago
$286 Roundtrip, found 1 hour ago
$286
Roundtrip
found 1 hour ago
Select United flight, departing Sun, May 24 from Louisville to Chicago, returning Wed, May 27, priced at $286 found 1 hour ago
United
Tue, Jun 23 - Wed, Jul 1
SDF
Louisville
ORD
Chicago
$288 Roundtrip, found 11 hours ago
$288
Roundtrip
found 11 hours ago
Select United flight, departing Tue, Jun 23 from Louisville to Chicago, returning Wed, Jul 1, priced at $288 found 11 hours ago
United
Wed, May 27 - Thu, May 28
SDF
Louisville
ORD
Chicago
$289 Roundtrip, found 6 hours ago
$289
Roundtrip
found 6 hours ago
Select United flight, departing Wed, May 27 from Louisville to Chicago, returning Thu, May 28, priced at $289 found 6 hours ago
Delta
Sun, May 24 - Wed, May 27
SDF
Louisville
ORD
Chicago
$295 Roundtrip, found 1 hour ago
$295
Roundtrip
found 1 hour ago
Select Delta flight, departing Sun, May 24 from Louisville to Chicago, returning Wed, May 27, priced at $295 found 1 hour ago
Southwest Airlines
Sun, May 24 - Wed, May 27
SDF
Louisville
ORD
Chicago
$295 Roundtrip, found 1 hour ago
$295
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sun, May 24 from Louisville to Chicago, returning Wed, May 27, priced at $295 found 1 hour ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $359
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $359

Frequently asked questions

How much does a flight from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $138 and cheap return flights from $275 Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights typically cost between $80 and $538, and return flights often range between $226 and $840. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
August is the cheapest month to fly from Louisville, KY (SDF) to Chicago, IL (ORD), with average round-trip fares around $207. This fare is about 25% lower than the average price for the year, likely due to reduced demand during the summer. Other affordable months to consider are March and December.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are 3 airlines offering direct flights from SDF to ORD:

  • United operates around 49 direct flights from SDF to ORD every week
  • American Airlines operates around 38 direct flights from SDF to ORD every week
  • British Airways operates around 25 direct flights from SDF to ORD every week

What is the cheapest airline that flies from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
United is one of the cheapest airlines offering nonstop flights from Louisville Intl. (SDF) to O'Hare Intl. (ORD), with round-trip tickets starting from around $77. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Louisville, KY (SDF) to Chicago, IL (ORD) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, American Airlines typically offers the lowest fares. American Airlines also offers the most daily flights from SDF to ORD, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly from Louisville, KY (SDF) to Chicago, IL (ORD) is typically in August or March. During these months, you can find return flights at around $207, making them the cheapest times to travel. August is popular for its warm weather and summer activities, while March offers a nice transition into spring, providing a great balance of price and travel experience.*Prices based on flights available on Expedia in the last year.
How many flights per day from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You can find approximately 13 nonstop flights per day from Louisville Intl. (SDF) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Louisville (SDF) to Chicago (ORD) typically departs at around 5:00 AM, operated by American Airlines. This seasonal service is available in January and December, allowing you to get an early start on your day in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Louisville (SDF) to Chicago (ORD) are in the early morning, from 6am to 9am. About 31% of passengers prefer this time window. Many major carriers, including Delta Airlines, American Airlines, and United Airlines, offer flights during this window. This timing is favored because it allows you to arrive in Chicago with plenty of time to start your day.
How long does it take to fly from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Flying nonstop from SDF to ORD takes around 1 hour 50 minutes, with the route covering approximately 286 miles. Flights with a layover typically take 5 hours 30 minutes longer than direct options. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You can fly first class between SDF and ORD. First class cabins are available on:

  • American Airlines
  • Delta Air Lines
  • United Airlines

How much is a business class flight from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A direct, return business class ticket from Louisville (SDF) to Chicago (ORD) typically costs between $589 - $965. A non-stop, one-way business class flight is usually around $351 - $553. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Louisville Intl. (SDF)?
From Louisville Intl. (SDF), you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD) in Chicago. Some flights may connect through major hubs like Baltimore Washington Intl. Thurgood Marshall (BWI), Harry Reid Intl. (LAS), Nashville Intl. (BNA) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Louisville, KY (SDF-Louisville Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

0
Origin airport
Louisville Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Southwest Airlines, United
Roundtrip price
$275
Distance
285 mi

Book with confidence

Louisville to Chicago Flights

The cheapest times to fly from Louisville to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Louisville to Chicago are during the month of May. You can find some of the cheapest flights from Louisville to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Louisville to Chicago

Sunday is one of the best days to book for cheap flights from Louisville to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Louisville to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Louisville to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $138 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Louisville to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Louisville to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Louisville to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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