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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Jun 17 — Jun 241
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 June 12, 2025.
Round-trip from | $97 (American Airlines) |
|---|---|
One-way from | $49 (Southwest) |
Popular in | March |
Cheapest in | April |
Average price | $275 |
Good round-trip deal | $318 or less |
Good one-way deal | $174 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 June 12, 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 June 12, 2025.
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Mon 8/46:50 pmSDF - ORD
Nonstop1h 35mAmerican Airlines
Wed 8/273:13 pmORD - SDF
Nonstop1h 25mAmerican Airlines
Deal found 6/12![American Airlines logo]()
$97
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/43:55 pmSDF - MDW
Nonstop1h 15mSouthwest
Wed 8/2710:05 amMDW - SDF
Nonstop1h 20mSouthwest
Deal found 6/10![Southwest logo]()
$97
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2910:55 amSDF - ORD
Nonstop1h 38mUnited Airlines
Mon 9/297:50 pmORD - SDF
Nonstop1h 40mUnited Airlines
Deal found 6/11![United Airlines logo]()
$116
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.
Tue 9/25:30 amSDF - ORD
1 stop7h 20mSouthwest
Tue 9/97:30 amORD - SDF
1 stop6h 05mSouthwest
Deal found 6/11![Southwest logo]()
$117
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/71:57 pmSDF - ORD
1 stop20h 41mSpirit Airlines
Thu 7/1011:21 amORD - SDF
1 stop20h 43mSpirit Airlines
Deal found 6/10![Spirit Airlines logo]()
$172
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.
Sat 8/3012:30 pmSDF - ORD
1 stop7h 49mDelta
Sat 9/65:30 pmORD - SDF
1 stop4h 30mDelta
Deal found 6/9![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 6/12. 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 11/1110:15 amSDF - MDW
1 stop3h 17mDelta
Tue 11/115:25 pmMDW - SDF
1 stop5h 31mDelta
Deal found 6/12![Delta logo]()
$177
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/169:46 amSDF - ORD
1 stop14h 27mMultiple Airlines
Sat 7/195:51 amORD - SDF
2 stops26h 13mMultiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$232
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/205:43 pmSDF - MDW
1 stop15h 39mAllegiant Air
Wed 7/234:27 pmMDW - SDF
1 stop17h 17mAllegiant Air
Deal found 6/11![Allegiant Air logo]()
$239
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, 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
6:50 pm-7:25 pm
Nonstop1h 35m
Chicago O'Hare Intl
Wed 8/27
3:13 pm-5:38 pm
Nonstop1h 25m
$97
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Mon 8/4
3:55 pm-4:10 pm
Nonstop1h 15m
Chicago Midway
Wed 8/27
10:05 am-12:25 pm
Nonstop1h 20m
$97
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Mon 9/29
10:55 am-11:33 am
Nonstop1h 38m
Chicago O'Hare Intl
Mon 9/29
7:50 pm-10:30 pm
Nonstop1h 40m
$116
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Tue 9/2
5:30 am-11:50 am
1 stop7h 20m
Chicago O'Hare Intl
Tue 9/9
7:30 am-2:35 pm
1 stop6h 05m
$117
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Mon 7/7
1:57 pm-9:38 am
1 stop20h 41m
Chicago O'Hare Intl
Thu 7/10
11:21 am-9:04 am
1 stop20h 43m
$172
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Sat 8/30
12:30 pm-7:19 pm
1 stop7h 49m
Chicago O'Hare Intl
Sat 9/6
5:30 pm-11:00 pm
1 stop4h 30m
$177
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Tue 11/11
10:15 am-12:32 pm
1 stop3h 17m
Chicago Midway
Tue 11/11
5:25 pm-11:56 pm
1 stop5h 31m
$177
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Wed 7/16
9:46 am-11:13 pm
1 stop14h 27m
Chicago O'Hare Intl
Sat 7/19
10:00 am-8:48 pm
1 stop9h 48m
$230
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Sun 7/20
5:43 pm-8:22 am
1 stop15h 39m
Chicago Midway
Wed 7/23
4:27 pm-10:44 am
1 stop17h 17m
$239
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Thu 8/7
11:50 am-4:25 pm
1 stop5h 35m
$49
Showing 1-10 of 19 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 9, 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 June 12, 2025.
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 44% 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 8, 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 June 12, 2025.
The most flights from SDF to CHI are scheduled on a Wednesday (45 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (31 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
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.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
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).
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, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Louisville to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.1
Entertainment
7.6
Overall
8.0
Boarding
8.2
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.1
Entertainment
7.6
Overall
8.0
Boarding
8.2
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.1
Entertainment
7.6
Overall
8.0
Boarding
8.2
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.1
Entertainment
7.6
Overall
8.0
Boarding
8.2
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.1
Entertainment
7.6
Overall
8.0
Boarding
8.2
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.1
Entertainment
7.6
Overall
8.0
Boarding
8.2
Comfort
8.0
Crew
8.6
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 June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$287 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$111 | Average$261 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$172 | Average$275 | FlexibilityNo cancel fee | On-time63% |