$49+ Cheap flights from Kentucky to Midway (MDW)
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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
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
Keep the following information in mind while searching for Kentucky to Midway flight deals. Data was last updated June 12, 2025.
Round-trip from | $97 (Southwest) |
|---|---|
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 Kentucky to Midway
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 June 12, 2025.
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 June 12, 2025.
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.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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.
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.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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.
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.
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 2,558,603 searches. Data last updated June 12, 2025.
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
Price
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
NashvilleChicago
BNA - MDW
BNAMDW
Nashville Intl
Thu 8/7
8:20 am-10:00 am
Nonstop1h 40m
Chicago Midway
Mon 8/11
7:55 am-9:25 am
Nonstop1h 30m
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
NashvilleChicago
BNA - MDW
BNAMDW
Nashville Intl
Thu 9/4
5:15 am-9:16 am
1 stop4h 01m
Chicago Midway
Tue 9/9
6:00 am-9:50 am
1 stop3h 50m
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Fri 9/5
6:40 am-6:50 am
Nonstop1h 10m
Chicago Midway
Sat 9/6
4:20 pm-6:30 pm
Nonstop1h 10m
KnoxvilleChicago
TYS - MDW
TYSMDW
Knoxville McGhee Tyson
Fri 7/18
1:31 pm-2:04 pm
Nonstop1h 33m
Chicago Midway
Mon 7/21
2:54 pm-5:20 pm
Nonstop1h 26m
LexingtonChicago
LEX - MDW
LEXMDW
Lexington Blue Grass
Fri 8/8
3:46 pm-9:42 pm
1 stop6h 56m
Chicago Midway
Mon 8/11
6:17 pm-10:46 pm
1 stop3h 29m
KnoxvilleChicago
TYS - MDW
TYSMDW
Knoxville McGhee Tyson
Tue 7/22
5:30 am-9:45 am
1 stop5h 15m
Chicago Midway
Tue 7/29
6:00 am-1:51 pm
1 stop6h 51m
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Sat 8/2
6:00 am-8:44 am
1 stop3h 44m
Chicago Midway
Sat 8/9
9:25 am-1:25 pm
1 stop3h 00m
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Mon 9/22
1:24 pm-11:25 pm
1 stop11h 01m
Chicago Midway
Wed 9/24
8:00 am-2:07 pm
1 stop5h 07m
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.
Cheapflights Insights
Everything you need to know about your flight from Kentucky to Chicago Midway Airport
What is the cheapest month to book a flight from Kentucky to Chicago Midway Airport?
Currently, April is the cheapest month in which you can book a flight from Kentucky to Chicago Midway Airport (average of $160). Flying from Kentucky to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 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 June 12, 2025.
When flying from Kentucky to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Rainfall in Midway by month
Plan your trip to Midway by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago Midway Airport 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 Midway Airport when rainfall is around 1.7 in.
Temperature in Midway by month
Plan your trip to Midway by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago Midway Airport, 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 Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated June 12, 2025.
Read through reviews of airlines operating flights from Kentucky to Chicago, such as Southwest, Delta and Allegiant Air. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
John,May 2025
PVD - BNA
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.
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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.
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 2,558,603 searches. Data last updated June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$172 | Average$275 | FlexibilityNo cancel fee | On-time63% |