HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kentucky

$55+ Cheap flights from Midway (MDW) to Kentucky

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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Kentucky 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 Midway to Kentucky

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Kentucky (USKY). 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 January 21, 2025.

Round-trip from

$110
(Frontier)

One-way from

$55
(Frontier)

Good round-trip deal

$293 or less

Good one-way deal

$159 or less
From Chicago Midway to Kentucky
Search Deals
One-way flight from Chicago Midway to Kentucky
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Kentucky.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Kentucky.
Search Deals

Find flight deals from Midway to Kentucky

Cheapest flights from Midway to Kentucky
Explore the most affordable flight options available from Midway to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.

This Frontier deal was found by Cheapflights users on 1/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1012:49 pmMDW - CVG
1 stop11h 33mFrontier
Tue 3/117:10 amCVG - MDW
1 stop9h 03mFrontier
Deal found 1/20$110
This Frontier deal was found by Cheapflights users on 1/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/76:40 amMDW - BNA
1 stop6h 28mFrontier
Thu 4/1012:58 pmBNA - MDW
1 stop11h 23mFrontier
Deal found 1/20$110
This Southwest deal was found by Cheapflights users on 1/20. 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.
Wed 2/196:25 amMDW - BNA
Nonstop1h 35mSouthwest
Wed 2/262:30 pmBNA - MDW
Nonstop1h 35mSouthwest
Deal found 1/20$117
This Southwest deal was found by Cheapflights users on 1/21. 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.
Thu 2/138:20 pmMDW - CVG
Nonstop1h 10mSouthwest
Mon 2/177:00 amCVG - MDW
Nonstop1h 15mSouthwest
Deal found 1/21$137
This Delta deal was found by Cheapflights users on 1/20. 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.
Fri 2/212:08 pmMDW - BNA
1 stop6h 48mDelta
Mon 2/242:20 pmBNA - MDW
1 stop3h 51mDelta
Deal found 1/20$177
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/164:59 pmMDW - SDF
1 stop4h 33mDelta
Wed 4/236:55 pmSDF - MDW
1 stop4h 34mDelta
Deal found 1/21$177
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/56:00 amMDW - CVG
1 stop7h 12mDelta
Wed 3/126:15 amCVG - MDW
2 stops9h 00mDelta
Deal found 1/21$182
This Delta deal was found by Cheapflights users on 1/20. 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.
Tue 3/46:00 amMDW - TYS
1 stop4h 23mDelta
Tue 3/1111:59 amTYS - MDW
1 stop5h 15mDelta
Deal found 1/20$199
This Frontier deal was found by Cheapflights users on 1/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/67:15 amMDW - TYS
1 stop7h 04mFrontier
Sun 2/94:19 pmTYS - MDW
1 stop8h 58mFrontier
Deal found 1/20$210
This Southwest deal was found by Cheapflights users on 1/20. 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.
Sat 2/158:15 pmMDW - SDF
Nonstop1h 15mSouthwest
Mon 2/177:00 amSDF - MDW
Nonstop1h 15mSouthwest
Deal found 1/20$216
This Delta deal was found by Cheapflights users on 1/20. 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.
Thu 2/202:08 pmMDW - LEX
1 stop6h 30mDelta
Sun 2/237:40 amLEX - MDW
1 stop6h 25mDelta
Deal found 1/20$237
This Booking.com deal was found by Cheapflights users on 1/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/293:52 pmMDW - TYS
Nonstop1h 28mAllegiant Air
Mon 9/12:29 pmTYS - MDW
Nonstop1h 33mAllegiant Air
Deal found 1/20$245

Find flights from Midway to Kentucky within your budget

Customize your flight search to find flights from Midway to Kentucky 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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Mon 3/10

12:49 pm-1:22 am

1 stop11h 33m

Cincinnati Cinci./N. Kentucky

Tue 3/11

7:10 am-3:13 pm

1 stop9h 03m

$110

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Mon 4/7

6:40 am-1:08 pm

1 stop6h 28m

Nashville Intl

Thu 4/10

12:58 pm-12:21 am

1 stop11h 23m

$110

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Wed 2/19

6:25 am-8:00 am

Nonstop1h 35m

Nashville Intl

Wed 2/26

2:30 pm-4:05 pm

Nonstop1h 35m

$117

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 2/13

8:20 pm-10:30 pm

Nonstop1h 10m

Cincinnati Cinci./N. Kentucky

Mon 2/17

7:00 am-7:15 am

Nonstop1h 15m

$137

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Fri 2/21

2:08 pm-8:56 pm

1 stop6h 48m

Nashville Intl

Wed 2/26

12:20 pm-4:20 pm

1 stop4h 00m

$177

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Wed 4/16

4:59 pm-10:32 pm

1 stop4h 33m

Louisville Intl

Wed 4/23

6:55 pm-10:29 pm

1 stop4h 34m

$177

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 2/20

10:57 am-4:58 pm

1 stop5h 01m

Cincinnati Cinci./N. Kentucky

Thu 2/27

10:31 am-5:43 pm

2 stops8h 12m

$182

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Tue 3/4

6:00 am-11:23 am

1 stop4h 23m

Knoxville McGhee Tyson

Tue 3/11

11:59 am-4:14 pm

1 stop5h 15m

$199

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Thu 2/6

7:15 am-3:19 pm

1 stop7h 04m

Knoxville McGhee Tyson

Sun 2/9

4:19 pm-12:17 am

1 stop8h 58m

$210

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Sat 2/15

8:15 pm-10:30 pm

Nonstop1h 15m

Louisville Intl

Mon 2/17

7:00 am-7:15 am

Nonstop1h 15m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 33 results
1
2
3
4

Best time to book a flight from Midway to Kentucky

Have a flexible travel schedule? Discover the best time to fly to Kentucky from Midway 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.

Travel insights for flights from Midway to Kentucky

Get recent, data-driven insights about flights from Midway to Kentucky including ideal travel times, pricing trends, and more.

What is the cheapest time of day to fly from MDW to KY?

Find hourly flight availability from Midway to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 21, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Kentucky as you normally would.

Weekly flight availability from Chicago Midway Airport to Kentucky

Explore weekly flight availability from Midway to Kentucky. 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 January 21, 2025.

The most flights from MDW to USKY are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Kentucky by month

Plan your trip to Kentucky by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kentucky ranges from 3.1 - 5.3 inches per month. May is typically the wettest month, when rainfall can reach 5.3 in. September is typically the driest time to visit Kentucky when rainfall is around 3.1 in.

Temperature in Kentucky by month

Plan your trip to Kentucky by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kentucky, 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 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 35.6 F).

Reviews of airlines servicing Kentucky

Get insights into the airlines that provide service to Kentucky. 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 Kentucky. Reviews last updated January 21, 2025.
Read through reviews of airlines operating flights from Chicago to Kentucky, such as Southwest, Delta and Frontier. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,443 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Midway to Kentucky. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Kentucky one-way?

    One-way options have recently been found by users for as low as $55 on Frontier. Other airlines that offer cheap prices include Southwest from $59 and Delta from $89 one-way.

  • What are the most popular routes from Chicago Midway Airport to Kentucky?

    While some choose either Chicago Midway - Knoxville McGhee Tyson or Chicago Midway - Cincinnati Cinci./N. Kentucky, Chicago Midway - Nashville Intl is the most popular route from Chicago Midway Airport to Kentucky.

  • What are the cheapest flights from Chicago Midway Airport to Kentucky?

    Looking at all options, your cheapest flight can be booked for $104. While the most popular route (Chicago Midway - Nashville Intl) can be booked for $137 on average our data indicates $303 when flying from Chicago Midway Airport to Kentucky.

  • Can I find deals for flights from Midway to Kentucky that include hotel bookings?

    Yes. In addition to deals on Midway to Kentucky flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Kentucky?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Kentucky.

  • Can I find deals for business class flights from Midway to Kentucky?

    Yes. Cheapflights offers flight deals from Midway to Kentucky by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Kentucky?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Kentucky (average of $299). Flying from Chicago Midway Airport to Kentucky in April is currently the most expensive (average of $369). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Tampa flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Denver flights
O'Hare Intl to Seattle flights
Midway to Sky Harbor Intl flights
Midway to Las Vegas flights
Midway to Dallas/Fort Worth flights
Midway to Orlando flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Boston flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Newark flights
O'Hare Intl to Austin flights
O'Hare Intl to Fort Myers flights
Midway to Miami flights
O'Hare Intl to Honolulu flights
O'Hare Intl to New Orleans flights
Midway to Tampa flights
O'Hare Intl to San Diego flights
Midway to Hobby flights
O'Hare Intl to West Palm Beach flights
Midway to Atlanta flights
Midway to Los Angeles flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Dulles Intl flights
Midway to Newark flights
O'Hare Intl to Nashville flights
O'Hare Intl to Baltimore flights
Midway to LaGuardia flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Charleston flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to George Bush Intcntl flights
Midway to John F Kennedy Intl flights
Midway to Denver flights
O'Hare Intl to Charlotte flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Ontario flights
Midway to New Orleans flights
O'Hare Intl to Burbank flights

Top airline flying from Midway to Kentucky

Discover the top airline that operate flights from Midway to Kentucky. 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$118Average$532FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.