MDW - SDF

$89 Find Cheap Flights from Chicago Midway Airport to Louisville - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Louisville departing on 9/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Louisville

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Louisville, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Louisville, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$215
Southwest
Sat 8/15Mon 8/17
MDW - SDF • Non-stop
Cheapest one-way
$89
Southwest
Tue 9/8
MDW - SDF • Non-stop
Top airlines
Southwest
Cheapest • from $215 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 1h 11m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
January
Cheapest • 100% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Louisville!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Louisville (MDW-SDF)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Louisville that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Louisville

Sat, Aug 15 - Mon, Aug 17
Southwest Logo
7:50 am - 10:10 am
MDW
-
SDF
1h 20mnonstop
Southwest Logo
2:15 pm - 2:30 pm
SDF
-
MDW
1h 15mnonstop
$215Southwest
Sat, Aug 15 - Mon, Aug 17
Southwest Logo
6:05 am - 3:10 pm
MDW
-
SDF
8h 05m
1 stop
Southwest Logo
9:00 am - 9:15 am
SDF
-
MDW
1h 15mnonstop
$225Southwest
Sat, Aug 15 - Mon, Aug 17
Southwest Logo
7:50 am - 10:10 am
MDW
-
SDF
1h 20mnonstop
Southwest Logo
3:20 pm - 9:55 pm
SDF
-
MDW
7h 35m
2 stops
$230Southwest
Sat, Aug 15 - Mon, Aug 17
Southwest Logo
7:05 am - 3:10 pm
MDW
-
SDF
7h 05m
1 stop
Southwest Logo
6:45 am - 12:15 pm
SDF
-
MDW
6h 30m
2 stops
$240Southwest
Wed, Jul 15 - Wed, Jul 22
Southwest Logo
7:45 am - 10:05 am
MDW
-
SDF
1h 20mnonstop
Southwest Logo
8:45 am - 9:00 am
SDF
-
MDW
1h 15mnonstop
$243Southwest
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
6:10 pm - 8:25 pm
MDW
-
SDF
1h 15mnonstop
Southwest Logo
2:15 pm - 2:30 pm
SDF
-
MDW
1h 15mnonstop
$244Southwest
Sat, Aug 15 - Mon, Aug 17
Southwest Logo
7:40 am - 5:15 pm
MDW
-
SDF
8h 35m
2 stops
Southwest Logo
6:45 am - 12:15 pm
SDF
-
MDW
6h 30m
2 stops
$245Southwest
Wed, Jul 15 - Wed, Jul 22
Southwest Logo
7:45 am - 10:05 am
MDW
-
SDF
1h 20mnonstop
Southwest Logo
5:35 am - 11:00 am
SDF
-
MDW
6h 25m
1 stop
$253Southwest
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
5:55 am - 1:05 pm
MDW
-
SDF
6h 10m
1 stop
Southwest Logo
2:15 pm - 2:30 pm
SDF
-
MDW
1h 15mnonstop
$254Southwest
Wed, Jul 15 - Wed, Jul 22
Southwest Logo
7:45 am - 10:05 am
MDW
-
SDF
1h 20mnonstop
Southwest Logo
7:25 am - 3:10 pm
SDF
-
MDW
8h 45m
2 stops
$258Southwest
Booking Insights

KAYAK's insights & trends for Midway to Louisville flights

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

How much is a round-trip flight from Chicago Midway Airport to Louisville?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Louisville departing in August.

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

The average price of all round-trip flights from Chicago Midway Airport to Louisville clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago Midway Airport to Louisville, look for departures on Thursdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Louisville, Saturday is the cheapest day to fly and Wednesday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Louisville, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Louisville is January, where tickets cost $0 (return) on average. On the other hand, the most expensive months are April and March, where the average cost of round-trip tickets is $745 and $480 respectively.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

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 $295 on average.

Find deals

Good to know

Low seasonOctober
Cheapest flight$89
Best time to beat the crowds with an average 61% drop in price.
Most popular time to fly and prices are also 40% lower on average.
Flight from Chicago Midway Airport to Louisville

When to book flights from Midway to Louisville

Are your dates flexible? Find out the best times to travel from Midway to Louisville based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Louisville flights

  • What is the cheapest flight from Chicago Midway Airport to Louisville?

    In the last 5 days, the lowest price for a flight from Chicago Midway Airport to Louisville was $89 for a one-way ticket and $215 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Louisville?

    No

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Louisville?

    American Airlines, and JetBlue offer inflight Wi-Fi service on the Chicago Midway Airport to Louisville flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Louisville?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to Louisville flight route.

  • On which days can I fly direct from Chicago Midway Airport to Louisville?

    There are nonstop flights from Chicago Midway Airport to Louisville on a daily basis.

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

    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 Louisville.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Louisville from Chicago Midway Airport 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 Louisville?

    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 to Louisville with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SDF can sometimes prove cheaper using this method.

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

    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 to Louisville from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Louisville

  • Looking for a cheap flight? 25% of our users found flights on this route for $146 or less one-way and $315 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Louisville?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Louisville Intl.
Find which airlines fly direct from Chicago Midway Airport to Louisville Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Louisville Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Louisville Intl to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Midway to Louisville

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Louisville. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Louisville? 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.
7.9
SouthwestOverall score based on 4235 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

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.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

Everything you need to know for your flight from Midway to Louisville

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Louisville (SDF)