$43 Find Cheap Flights from Chicago Midway Airport to Kentucky - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Cincinnati
Cincinnati
1h 10mNonstop
from $164per person
Louisville
Louisville
1h 10mNonstop
from $197per person
Nashville
Nashville
1h 25mNonstop
from $240per person
Knoxville
Knoxville
1h 25mNonstop
from $251per person
Lexington
Lexington
4h 38m2 stops
from $299per person
Blountville
Blountville
4h 10m2 stops
from $299per person
Explore the map

Book Cheap Midway to Kentucky Plane Tickets

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Kentucky

Wed, Oct 28 - Wed, Nov 4
Frontier Logo
6:42 pm - 9:19 amMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
13h 37m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:36 pm - 5:47 pmCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
6h 11m1 stop Atlanta Hartsfield-Jackson
$164Frontier
Tue, Oct 20 - Wed, Oct 21
Frontier Logo
6:21 am - 11:43 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
16h 22m2 stops Atlanta Hartsfield-Jackson Orlando
Frontier Logo
12:43 pm - 11:43 pmCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
12h 00m1 stop Atlanta Hartsfield-Jackson
$195Frontier
Mon, Oct 19 - Wed, Oct 21
Southwest Logo
7:55 am - 10:10 amMDW  Chicago Midway-SDF Louisville Intl
1h 15mnonstop
Southwest Logo
8:35 am - 8:50 amSDF  Louisville Intl-MDW Chicago Midway
1h 15mnonstop
$197Southwest
Sat, Oct 24 - Sat, Oct 31
Southwest Logo
8:05 am - 10:20 amMDW  Chicago Midway-SDF Louisville Intl
1h 15mnonstop
Southwest Logo
12:35 pm - 12:50 pmSDF  Louisville Intl-MDW Chicago Midway
1h 15mnonstop
$197Southwest
Thu, Oct 29 - Tue, Nov 3
Frontier Logo
6:42 pm - 1:54 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
18h 12m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:43 pm - 5:47 pmCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
6h 04m1 stop Atlanta Hartsfield-Jackson
$204Frontier
Mon, Oct 19 - Wed, Oct 21
Southwest Logo
7:55 am - 10:10 amMDW  Chicago Midway-SDF Louisville Intl
1h 15mnonstop
Southwest Logo
3:00 pm - 10:20 pmSDF  Louisville Intl-MDW Chicago Midway
8h 20m1 stop Dallas Love Field
$207Southwest
Wed, Sep 30 - Wed, Oct 7
Frontier Logo
6:25 am - 11:38 amMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
28h 13m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:43 pm - 5:51 pmCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
6h 08m1 stop Atlanta Hartsfield-Jackson
$209Frontier
Fri, Oct 2 - Mon, Oct 5
Allegiant Air Logo
2:24 pm - 4:49 pmMDW  Chicago Midway-TYS Knoxville McGhee Tyson
1h 25mnonstop
Allegiant Air Logo
11:34 am - 12:06 pmTYS  Knoxville McGhee Tyson-MDW Chicago Midway
1h 32mnonstop
$251Allegiant Air
Fri, Oct 2 - Fri, Oct 9
Allegiant Air Logo
2:24 pm - 4:49 pmMDW  Chicago Midway-TYS Knoxville McGhee Tyson
1h 25mnonstop
Allegiant Air Logo
9:26 am - 8:35 pmTYS  Knoxville McGhee Tyson-MDW Chicago Midway
12h 09m1 stop Valparaiso Destin-Ft Walton Beach
$254Allegiant Air
Mon, Oct 19 - Thu, Oct 22
Allegiant Air Logo
1:26 pm - 3:51 pmMDW  Chicago Midway-TYS Knoxville McGhee Tyson
1h 25mnonstop
Allegiant Air Logo
6:23 pm - 8:25 pmTYS  Knoxville McGhee Tyson-MDW Chicago Midway
27h 02m1 stop Valparaiso Destin-Ft Walton Beach
$260Allegiant Air
Booking Insights

KAYAK's insights & trends for Midway to Kentucky flights

Get data-powered insights and trends into flights from Midway to Kentucky to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Kentucky flight route?

The cheapest ticket to Kentucky from Chicago Midway Airport found in the last 5 days was to Louisville, at $227 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Louisville (SDF), and the cheapest round-trip airline ticket found on this route in the last 5 days was $227.

What is the cheapest time of day to fly to Kentucky?

The cheapest time of day to fly to Kentucky is generally in the afternoon, when round-trip flights cost $328 on average. Morning departures are around 4% cheaper than evening flights, on average. The most expensive time of day to fly to Kentucky is generally at night, which is peak travel time and where the average cost of a ticket is $521.

Can I save money by flying with a layover from Chicago Midway Airport to Kentucky?

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $252 on average.

What is the cheapest month to fly from Chicago Midway Airport to Kentucky?

The cheapest month for flights from Chicago Midway Airport to Kentucky is January, when tickets cost $0 (return) on average. On the other hand, the most expensive months are June and April, when the average cost of round-trip tickets is $757 and $745 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Kentucky?

When flying from Chicago Midway Airport to Kentucky, you should consider leaving on a Wednesday and avoid Mondays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Saturdays and the most expensive ones on Mondays.

Find deals

Good to know

Low season

December

Cheapest flight

$43
Best time to beat the crowds with an average 40% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chicago Midway Airport to Knoxville

FAQs - booking Kentucky flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Kentucky?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Kentucky.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Kentucky?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Kentucky is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Kentucky?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago Midway Airport to Kentucky with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Kentucky?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago Midway Airport to Kentucky up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Kentucky

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Nashville $179 one-way - $289 round-trip

Reviews of the top airline flying from Midway to Kentucky

 
Need help choosing which airline to fly with from Midway to Kentucky? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4190 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

More options for your flight from Midway to Kentucky

Complete your trip to Kentucky with a hotel stay or car rental

Car rentals in Kentucky
Hotels in Kentucky
Vacations in Kentucky