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.
$49+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Jul 8 — Jul 151
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Louisville to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Louisville Intl to Chicago are usually found in April or August, booked 61 days in advance, depart on a Thursday or Friday and return on a Saturday
Cheap 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 July 3, 2025.
Round-trip from | $97 (United Airlines) |
|---|---|
One-way from | $49 (United Airlines) |
Popular in | March |
Cheapest in | April |
Average price | $255 |
Good round-trip deal | $287 or less |
Good one-way deal | $159 or less |
Find flight deals from Louisville to Chicago
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 July 3, 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 July 3, 2025.
This United Airlines deal was found by Cheapflights users on 7/3. 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 8/46:08 pmSDF - ORD
Nonstop1h 42mUnited Airlines
Tue 8/510:55 amORD - SDF
Nonstop1h 29mUnited Airlines
Deal found 7/3![United Airlines logo]()
$97
This Southwest deal was found by Cheapflights users on 7/1. 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.
Thu 8/71:15 pmSDF - MDW
Nonstop1h 15mSouthwest
Mon 8/118:35 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 7/1![Southwest logo]()
$97
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Thu 8/76:08 pmSDF - ORD
Nonstop1h 40mAmerican Airlines
Mon 8/116:49 amORD - SDF
Nonstop1h 24mAmerican Airlines
Deal found 7/1![American Airlines logo]()
$98
This Southwest deal was found by Cheapflights users on 7/1. 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.
Tue 10/145:30 amSDF - ORD
1 stop7h 20mSouthwest
Wed 10/151:50 pmORD - SDF
1 stop6h 50mSouthwest
Deal found 7/1![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 7/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/77:50 amSDF - ORD
1 stop3h 26mDelta
Mon 8/112:00 pmORD - SDF
1 stop6h 15mDelta
Deal found 7/2![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/512:50 pmSDF - MDW
1 stop4h 20mDelta
Wed 8/1312:43 pmMDW - SDF
1 stop4h 57mDelta
Deal found 7/1![Delta logo]()
$177
This Mytrip deal was found by Cheapflights users on 7/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/107:45 amSDF - ORD
1 stop9h 27mSpirit Airlines
Fri 9/126:30 amORD - SDF
1 stop16h 05mSpirit Airlines
Deal found 7/3![Spirit Airlines logo]()
$212
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/910:57 amSDF - ORD
1 stop7h 20mMultiple Airlines
Sun 8/1010:00 amORD - SDF
1 stop6h 58mMultiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$229
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 July 3, 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 - ORD
SDFORD
Louisville Intl
Mon 8/4
6:08 pm-6:50 pm
Nonstop1h 42m
Chicago O'Hare Intl
Tue 8/5
10:55 am-1:24 pm
Nonstop1h 29m
$97
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Thu 8/7
7:10 pm-7:30 pm
Nonstop1h 20m
Chicago Midway
Mon 8/11
10:00 am-12:20 pm
Nonstop1h 20m
$97
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Thu 8/7
6:08 pm-6:48 pm
Nonstop1h 40m
Chicago O'Hare Intl
Mon 8/11
6:49 am-9:13 am
Nonstop1h 24m
$98
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Thu 9/4
11:50 am-4:25 pm
1 stop5h 35m
Chicago O'Hare Intl
Thu 9/11
1:50 pm-11:30 pm
1 stop8h 40m
$122
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Thu 8/7
7:50 am-10:16 am
1 stop3h 26m
Chicago O'Hare Intl
Mon 8/11
2:00 pm-9:15 pm
1 stop6h 15m
$177
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Tue 8/5
12:50 pm-4:10 pm
1 stop4h 20m
Chicago Midway
Wed 8/13
12:43 pm-6:40 pm
1 stop4h 57m
$177
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Wed 9/10
7:45 am-4:12 pm
1 stop9h 27m
Chicago O'Hare Intl
Fri 9/12
6:30 am-11:35 pm
1 stop16h 05m
$212
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Sat 8/9
10:57 am-5:17 pm
1 stop7h 20m
Chicago O'Hare Intl
Sun 8/10
10:00 am-5:58 pm
1 stop6h 58m
$229
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Thu 8/7
8:40 am-9:17 am
Nonstop1h 37m
$49
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Mon 8/11
7:10 pm-7:30 pm
Nonstop1h 20m
$49
Showing 1-10 of 18 results
The best insider tips for Louisville to Chicago flights
Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Louisville to Chicago trip
Airlines
![Southwest]()
Southwest
![United Airlines]()
United Airlines
Basic Economy allows a personal item only; no carry-on bags unless exceptions apply.
Economy Plus offers extra legroom seats towards the front of the economy cabin.
Our travel experts
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 June 27, 2025.
To ensure you get the cheapest price possible for a flight from Louisville to Chicago, you should look to book at least 61 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 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 July 3, 2025.
One of the essential ways to save on airfare from Louisville to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 42% 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 June 29, 2025.
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
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 July 3, 2025.
The most flights from SDF to CHI are scheduled on a Thursday (46 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 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 July 3, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United 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.
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
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.
Traveling to a place near Louisville?
Book flights to Louisville if you plan to visit one of these locationsMerrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Louisville to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 July 3, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$102 | Average$280 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$110 | Average$255 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$275 | FlexibilityNo cancel fee | On-time63% |