$95+ Cheap flights from Louisville (SDF) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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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 January or December, booked 42 days in advance, depart on a Friday or Thursday and return on a Thursday
Cheap flight deals from Louisville to Chicago
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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 October 25, 2026.
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 October 25, 2026.
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/96:31 pm -
Nonstop1h 59m
Thu 11/126:59 pm -
Nonstop1h 37m
Deal found 10/23![American Airlines logo]()
$189
This Southwest deal was found by Cheapflights users on 10/20. 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 11/127:55 pm -
Nonstop1h 15m
Sun 11/1512:50 pm -
Nonstop1h 15m
Deal found 10/20![Southwest logo]()
$191
This United Airlines deal was found by Cheapflights users on 10/23. 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 11/105:57 pm -
Nonstop1h 52m
Wed 11/117:55 pm -
Nonstop1h 35m
Deal found 10/23![United Airlines logo]()
$205
This Southwest deal was found by Cheapflights users on 10/21. 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 11/108:50 am -
Nonstop1h 15m
Wed 11/111:15 pm -
2 stops8h 00m
Deal found 10/21![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 10/22. 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 12/73:50 pm -
1 stop7h 55m
Thu 12/108:15 am -
Nonstop1h 15m
Deal found 10/22![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 10/23. 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 11/93:14 pm -
1 stop4h 16m
Thu 11/121:30 pm -
1 stop6h 24m
Deal found 10/23![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 10/23. 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 11/93:14 pm -
1 stop3h 50m
Thu 11/129:30 am -
1 stop3h 54m
Deal found 10/23![Delta logo]()
$209
This Southwest deal was found by Cheapflights users on 10/21. 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.
Fri 12/43:10 pm -
1 stop7h 20m
Sun 12/67:20 am -
1 stop7h 05m
Deal found 10/21![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 10/20. 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.
Fri 11/138:45 am -
Nonstop1h 15m
Fri 11/1311:10 am -
2 stops10h 05m
Deal found 10/20![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 10/21. 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 11/105:40 am -
1 stop4h 20m
Tue 11/101:15 pm -
2 stops8h 00m
Deal found 10/21![Southwest logo]()
$216
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/126:27 am -
Nonstop1h 48m
Sat 11/146:59 pm -
Nonstop1h 37m
Deal found 10/21![American Airlines logo]()
$219
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Sat 12/56:15 am -
Nonstop1h 44m
Sat 12/123:30 pm -
Nonstop1h 42m
Deal found 10/20![American Airlines logo]()
$220
Best flights from Louisville to ChicagoDiscover carefully curated flight deals from Louisville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
Discover carefully curated flight deals from Louisville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
This Southwest deal was found by Cheapflights users on 10/23. 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.
Fri 11/137:55 pm -
Nonstop1h 15m
Sun 11/157:45 am -
Nonstop1h 20m
Deal found 10/23![Southwest logo]()
$191
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/105:10 am -
Nonstop1h 45m
Wed 11/116:10 pm -
Nonstop1h 42m
Deal found 10/20![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 10/20. 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 12/53:12 pm -
1 stop4h 57m
Sat 12/1210:36 am -
1 stop5h 17m
Deal found 10/20![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 10/22. 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 11/128:45 am -
Nonstop1h 15m
Thu 11/126:40 pm -
Nonstop1h 25m
Deal found 10/22![Southwest logo]()
$191
This United Airlines deal was found by Cheapflights users on 10/24. 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 12/187:00 am -
Nonstop1h 49m
Mon 12/217:55 pm -
Nonstop1h 44m
Deal found 10/24![United Airlines logo]()
$225
This Southwest deal was found by Cheapflights users on 10/23. 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 11/102:05 pm -
Nonstop1h 20m
Wed 11/1111:30 am -
2 stops8h 10m
Deal found 10/23![Southwest logo]()
$206
This Delta deal was found by Cheapflights users on 10/20. 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 11/95:59 pm -
1 stop6h 55m
Thu 11/126:49 am -
1 stop4h 07m
Deal found 10/20![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 10/22. 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 12/73:50 pm -
1 stop7h 55m
Thu 12/108:15 am -
Nonstop1h 15m
Deal found 10/22![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 10/22. 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 11/1210:49 am -
1 stop6h 29m
Sat 11/142:44 pm -
1 stop5h 29m
Deal found 10/22![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 10/23. 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.
Sat 12/1212:45 pm -
1 stop3h 50m
Sun 12/137:50 am -
2 stops8h 10m
Deal found 10/23![Southwest logo]()
$216
This Delta deal was found by Cheapflights users on 10/22. 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 11/2410:49 am -
1 stop6h 29m
Thu 11/2611:18 am -
1 stop3h 41m
Deal found 10/22![Delta logo]()
$239
This United Airlines deal was found by Cheapflights users on 10/23. 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 1/510:20 am -
Nonstop1h 49m
Sat 1/91:55 pm -
Nonstop1h 40m
Deal found 10/23![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 10/22. 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.
Wed 11/111:01 pm -
1 stop4h 17m
Sat 11/1412:30 pm -
1 stop4h 50m
Deal found 10/22![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 10/24. 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 11/192:05 pm -
Nonstop1h 20m
Fri 11/2712:50 pm -
Nonstop1h 15m
Deal found 10/24![Southwest logo]()
$225
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/135:10 am -
Nonstop1h 45m
Fri 11/137:55 pm -
Nonstop1h 35m
Deal found 10/20![United Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 10/24. 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 12/244:38 pm -
1 stop7h 29m
Tue 1/55:30 am -
1 stop5h 36m
Deal found 10/24![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 10/24. 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.
Fri 12/188:35 pm -
Nonstop1h 25m
Mon 12/217:40 am -
Nonstop1h 20m
Deal found 10/24![Southwest logo]()
$225
This Southwest deal was found by Cheapflights users on 10/24. 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 12/93:50 pm -
1 stop4h 15m
Thu 12/108:15 am -
Nonstop1h 15m
Deal found 10/24![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 10/22. 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.
Wed 12/168:05 am -
1 stop7h 44m
Sun 12/205:25 am -
1 stop7h 10m
Deal found 10/22![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 10/24. 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.
Sat 11/149:10 am -
Nonstop1h 15m
Fri 11/2012:50 pm -
Nonstop1h 15m
Deal found 10/24![Southwest logo]()
$238
Last-minute flights from Louisville to ChicagoDiscover last-minute flight deals from Louisville to Chicago. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Louisville to Chicago. Data last updated October 25, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/96:31 pm -
Nonstop1h 59m
Thu 11/126:59 pm -
Nonstop1h 37m
Deal found 10/23![American Airlines logo]()
$189
This Delta deal was found by Cheapflights users on 10/23. 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 11/93:14 pm -
1 stop4h 16m
Thu 11/121:30 pm -
1 stop6h 24m
Deal found 10/23![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 10/23. 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 11/93:14 pm -
1 stop3h 50m
Thu 11/129:30 am -
1 stop3h 54m
Deal found 10/23![Delta logo]()
$209
This United Airlines deal was found by Cheapflights users on 10/23. 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 11/105:57 pm -
Nonstop1h 52m
Wed 11/117:55 pm -
Nonstop1h 35m
Deal found 10/23![United Airlines logo]()
$205
This Southwest deal was found by Cheapflights users on 10/21. 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 11/108:50 am -
Nonstop1h 15m
Wed 11/111:15 pm -
2 stops8h 00m
Deal found 10/21![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 10/21. 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 11/105:40 am -
1 stop4h 20m
Tue 11/101:15 pm -
2 stops8h 00m
Deal found 10/21![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 10/20. 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 11/127:55 pm -
Nonstop1h 15m
Sun 11/1512:50 pm -
Nonstop1h 15m
Deal found 10/20![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/126:27 am -
Nonstop1h 48m
Sat 11/146:59 pm -
Nonstop1h 37m
Deal found 10/21![American Airlines logo]()
$219
This Southwest deal was found by Cheapflights users on 10/20. 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.
Fri 11/138:45 am -
Nonstop1h 15m
Fri 11/1311:10 am -
2 stops10h 05m
Deal found 10/20![Southwest logo]()
$212
This United Airlines deal was found by Cheapflights users on 10/24. 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.
Sat 11/149:17 am -
Nonstop1h 43m
Fri 11/206:10 pm -
Nonstop1h 42m
Deal found 10/24![United Airlines logo]()
$225
This Southwest deal was found by Cheapflights users on 10/24. 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 11/192:05 pm -
Nonstop1h 20m
Fri 11/2712:50 pm -
Nonstop1h 15m
Deal found 10/24![Southwest logo]()
$225
This American Airlines deal was found by Cheapflights users on 10/22. 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.
Sat 11/216:24 am -
Nonstop1h 51m
Mon 11/232:42 pm -
Nonstop1h 31m
Deal found 10/22![American Airlines logo]()
$228
One-way flights from Louisville to ChicagoSearch for one-way flight options from Louisville to Chicago. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from Louisville to Chicago. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This American Airlines deal was found by Cheapflights users on 10/23. 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 12/255:45 am -
Nonstop1h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![American Airlines logo]()
$95
This Southwest deal was found by Cheapflights users on 10/24. 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 11/182:05 pm -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Southwest logo]()
$95
This Southwest deal was found by Cheapflights users on 10/21. 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 11/107:35 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$96
This Delta deal was found by Cheapflights users on 10/24. 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 11/163:00 pm -
1 stop6h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$105
This Delta deal was found by Cheapflights users on 10/24. 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 11/163:14 pm -
1 stop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$105
This American Airlines deal was found by Cheapflights users on 10/21. 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 1/181:11 pm -
Nonstop1h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$110
This Southwest deal was found by Cheapflights users on 10/22. 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.
Sun 12/612:05 pm -
2 stops9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$111
This Delta deal was found by Cheapflights users on 10/23. 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 1/912:53 pm -
1 stop4h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Delta logo]()
$113
This Southwest deal was found by Cheapflights users on 10/24. 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 11/234:40 pm -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Southwest logo]()
$113
This Southwest deal was found by Cheapflights users on 10/23. 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.
Fri 12/257:20 am -
2 stops9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$117
This Trip.com deal was found by Cheapflights users on 10/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:49 am -
1 stop4h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$118
This Trip.com deal was found by Cheapflights users on 10/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/253:14 pm -
1 stop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$118
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 October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $189 (American Airlines) |
One-way from | $95 (American Airlines) |
Popular in | August |
Cheapest in | January |
Average price | $291 |
Good round-trip deal | $327 or less |
Good one-way deal | $213 or less |
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 7,457,451 searches. Data last updated October 25, 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
Cheapest round-trip
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Fri 12/25
2:05 pm-2:25 pm
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$96
Quickest round-trip
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Tue 11/10
7:35 pm-7:50 pm
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$96
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Thu 11/12
8:45 am-9:00 am
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$96
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Thu 11/19
6:00 am-11:59 am
1 stop6h 59m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$105
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Sat 12/5
12:45 pm-3:35 pm
1 stop3h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$106
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Thu 11/26
7:15 am-2:30 pm
1 stop8h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$106
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Sun 12/6
12:05 pm-8:05 pm
2 stops9h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$111
LouisvilleChicago
SDF Louisville Intl - ORD Chicago O'Hare Intl
SDFORD
Louisville Intl
Wed 11/18
5:10 am-5:55 am
Nonstop1h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$113
LouisvilleChicago
SDF Louisville Intl - ORD Chicago O'Hare Intl
SDFORD
Louisville Intl
Fri 12/11
1:59 pm-2:40 pm
Nonstop1h 41m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$113
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Sat 1/9
7:20 am-12:33 pm
1 stop6h 13m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$113
Showing 1-10 of 40 resultsSorted by cheapest first
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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
SDF-CHI
SDF-ORD
SDF-MDW
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
SDF-CHI
SDF-ORD
SDF-MDW
What is the cheapest month to book a flight from Louisville to Chicago?
Currently, March is the cheapest month in which you can book a flight from Louisville to Chicago (average of $277). Flying from Louisville to Chicago in August is currently the most expensive (average of $391). 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 October 25, 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 31% 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 October 25, 2026.
The most flights from SDF to CHI are scheduled on a Friday (48 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (9 on average).
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 $274 and $362 in November.The cheapest round-trip price found within the last 5 days was $189 on American Airlines (Nov 9-Nov 12).
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 October 24, 2026.
Travelers seeking maximum savings on their Louisville to Chicago flight should consider departing on Friday 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 October 25, 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.
Crew
8.6
Comfort
8.0
Entertainment
7.4
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.4
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.4
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.4
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Complete your trip
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Louisville and Chicago flights
Browse other Louisville and Chicago flight options. Last updated on October 25, 2026.
Other flights from Louisville
Browse through other flights departing from Louisville. Flights are based on user searches made on Cheapflights and were last updated on October 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$178 | Average$393 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$187 | Average$337 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$197 | Average$314 | FlexibilityNo cancel fee | On-time71% |