$99+ Cheap flights from Kentucky to Midway (MDW)
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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
Oct 26 — Nov 21
Round-trip
1 adult, Economy
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Find cheap flights from Kentucky to Midway 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.Cheap flight deals from Kentucky to Midway
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Best
Last-minute
One-way
Cheapest flights from Kentucky to MidwayExplore the most affordable flight options available from Kentucky to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 26, 2026.
Explore the most affordable flight options available from Kentucky to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 26, 2026.
This Southwest deal was found by Cheapflights users on 9/23. 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.
Thu 10/157:50 pm -
Nonstop1h 15m
Mon 10/197:55 am -
Nonstop1h 15m
Deal found 9/23![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 9/23. 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.
Wed 10/218:35 am -
Nonstop1h 15m
Wed 10/282:45 pm -
2 stops4h 50m
Deal found 9/23![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 9/22. 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.
Sat 10/175:05 pm -
Nonstop1h 20m
Sat 10/246:45 am -
1 stop7h 10m
Deal found 9/22![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 9/21. 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 11/134:40 pm -
Nonstop1h 20m
Mon 11/168:15 am -
Nonstop1h 15m
Deal found 9/21![Southwest logo]()
$214
This Delta deal was found by Cheapflights users on 9/23. 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.
Thu 11/128:05 am -
1 stop4h 54m
Sat 11/144:13 pm -
1 stop6h 00m
Deal found 9/23![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 9/21. 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.
Wed 10/284:00 pm -
2 stops7h 00m
Wed 11/411:30 am -
2 stops8h 10m
Deal found 9/21![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 9/23. 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.
Thu 10/225:35 am -
1 stop5h 25m
Mon 10/264:30 pm -
1 stop5h 05m
Deal found 9/23![Southwest logo]()
$234
Best flights from Kentucky to MidwayDiscover carefully curated flight deals from Kentucky to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 26, 2026.
Discover carefully curated flight deals from Kentucky to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 26, 2026.
This Southwest deal was found by Cheapflights users on 9/22. 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 11/192:05 pm -
Nonstop1h 20m
Sat 11/217:55 am -
Nonstop1h 20m
Deal found 9/22![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 9/24. 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.
Wed 10/282:36 pm -
1 stop4h 24m
Wed 11/411:39 am -
1 stop6h 31m
Deal found 9/24![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 9/21. 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.
Wed 11/42:05 pm -
Nonstop1h 20m
Wed 11/46:15 pm -
Nonstop1h 20m
Deal found 9/21![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 9/24. 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 10/157:50 pm -
Nonstop1h 15m
Mon 10/197:55 am -
Nonstop1h 15m
Deal found 9/24![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 9/24. 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 11/128:05 am -
1 stop4h 54m
Sat 11/144:13 pm -
1 stop6h 00m
Deal found 9/24![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 9/25. 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 12/59:10 am -
Nonstop1h 15m
Mon 12/71:15 pm -
2 stops7h 55m
Deal found 9/25![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 9/25. 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 12/257:35 pm -
Nonstop1h 15m
Tue 12/297:40 am -
Nonstop1h 20m
Deal found 9/25![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 9/21. 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 11/134:40 pm -
Nonstop1h 20m
Sat 11/148:00 am -
2 stops7h 25m
Deal found 9/21![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 9/22. 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 10/227:15 am -
2 stops8h 40m
Mon 10/267:55 am -
Nonstop1h 15m
Deal found 9/22![Southwest logo]()
$263
Last-minute flights from Kentucky to MidwayDiscover last-minute flight deals from Kentucky to Midway. Data last updated September 26, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Midway. Data last updated September 26, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/23. 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.
Thu 10/157:50 pm -
Nonstop1h 15m
Mon 10/197:55 am -
Nonstop1h 15m
Deal found 9/23![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 9/22. 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.
Sat 10/175:05 pm -
Nonstop1h 20m
Sat 10/246:45 am -
1 stop7h 10m
Deal found 9/22![Southwest logo]()
$213
This Delta deal was found by Cheapflights users on 9/22. 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.
Sat 10/175:59 pm -
1 stop5h 34m
Sat 10/2412:27 pm -
1 stop4h 32m
Deal found 9/22![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 9/23. 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.
Wed 10/218:35 am -
Nonstop1h 15m
Wed 10/282:45 pm -
2 stops4h 50m
Deal found 9/23![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 9/24. 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 10/227:50 pm -
Nonstop1h 15m
Sat 10/248:10 am -
2 stops7h 15m
Deal found 9/24![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 9/23. 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.
Thu 10/225:35 am -
1 stop5h 25m
Mon 10/264:30 pm -
1 stop5h 05m
Deal found 9/23![Southwest logo]()
$234
This Southwest deal was found by Cheapflights users on 9/21. 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.
Wed 10/284:00 pm -
2 stops7h 00m
Wed 11/411:30 am -
2 stops8h 10m
Deal found 9/21![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 9/21. 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 10/303:35 pm -
Nonstop1h 15m
Mon 11/212:50 pm -
Nonstop1h 15m
Deal found 9/21![Southwest logo]()
$214
One-way flights from Kentucky to MidwaySearch for one-way flight options from Kentucky to Midway. Find affordable one-way fares based on user searches. Data last updated September 26, 2026.
Search for one-way flight options from Kentucky to Midway. Find affordable one-way fares based on user searches. Data last updated September 26, 2026.
This Southwest deal was found by Cheapflights users on 9/24. 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.
Tue 10/272:05 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Southwest logo]()
$99
This Southwest deal was found by Cheapflights users on 9/23. 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.
Wed 10/213:00 pm -
1 stop8h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Southwest logo]()
$109
This Southwest deal was found by Cheapflights users on 9/22. 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.
Fri 11/67:55 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$116
This Delta deal was found by Cheapflights users on 9/23. 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.
Fri 12/2512:45 pm -
1 stop5h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Delta logo]()
$126
This Southwest deal was found by Cheapflights users on 9/21. 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.
Sat 10/247:05 am -
2 stops7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$131
This Southwest deal was found by Cheapflights users on 9/25. 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 11/47:20 am -
2 stops9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Southwest logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:08 pm -
2 stops23h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$154
This Southwest deal was found by Cheapflights users on 9/22. 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 10/225:35 am -
1 stop4h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$160
This Southwest deal was found by Cheapflights users on 9/25. 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 11/248:35 pm -
Nonstop1h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Southwest logo]()
$163
Find flight deals from Kentucky to Midway
Keep the following information in mind while searching for Kentucky to Midway flight deals. Data was last updated September 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $197 (Southwest) |
One-way from | $99 (Southwest) |
Popular in | January |
Cheapest in | December |
Average price | $374 |
Good round-trip deal | $339 or less |
Good one-way deal | $202 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky to Midway 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 September 26, 2026.
Use the filters below to find and compare flights from Kentucky to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Thu 10/22
7:50 pm-8:05 pm
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$99
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Thu 10/15
3:35 pm-3:50 pm
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$99
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Tue 12/22
8:35 pm-9:00 pm
Nonstop1h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$99
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Tue 10/27
2:05 pm-2:20 pm
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$99
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Mon 10/26
5:57 pm-10:33 pm
1 stop5h 36m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Tue 10/20
5:57 pm-10:33 pm
1 stop5h 36m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Thu 12/24
4:38 pm-10:22 pm
1 stop6h 44m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Wed 10/28
12:40 pm-4:47 pm
1 stop5h 07m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Tue 10/20
3:00 pm-10:20 pm
1 stop8h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Thu 11/19
2:05 pm-2:25 pm
Nonstop1h 20m
Chicago Midway
Sat 11/21
7:55 am-10:15 am
Nonstop1h 20m
$197
Showing 1-10 of 18 resultsSorted by cheapest first
Best time to book a flight from Kentucky to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Kentucky with our price prediction graph.
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 Kentucky to Chicago Midway Airport
USKY-MDW
SDF-MDW
What is the cheapest time of day to fly from KY to MDW?
Find hourly flight availability from Kentucky to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 26, 2026.
It’s optimal to fly from Kentucky to Chicago Midway Airport in the evening. By choosing this option you can save up to 8% on the cost of your flight, compared to a flight in the morning.
How much does it cost to fly round-trip from Kentucky to Chicago Midway Airport?
Airfare is below average for this route at the moment.
Kentucky to Chicago Midway Airport flights typically cost between $339 and $685 in October.The cheapest round-trip price found within the last 5 days was $197 on Southwest (Oct 15-Oct 19).
Related info for your journey
Find useful and relevant information for your journey from Kentucky to Midway. 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 Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Kentucky to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kentucky to Midway by cabin class
Find flights from Kentucky to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 26, 2026.
Kentucky and Midway flights
Browse other Kentucky and Midway flight options. Last updated on September 26, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Kentucky to Midway flights
Consider these flights traveling from Kentucky to Midway.
Top airline flying from Kentucky to Midway
Discover the top airline that operate flights from Kentucky to Midway. 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 September 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$187 | Average$315 | FlexibilityNo cancel fee | On-time63% |