SDF - MDW

$67 Find Cheap Flights from Louisville to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Louisville to Midway departing on 1/7. 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 Chicago Midway Airport

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

Cheapest round-trip
$171
Overall average: $186
Southwest
Thu 1/8Mon 1/12
SDF - MDW • Non-stop
Cheapest one-way
$67
Typical prices: $282-$302
Southwest
Wed 1/7
SDF - MDW • Non-stop
Top airlines
Southwest
Cheapest • from $171 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 48% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Louisville to Midway (SDF-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Louisville to Midway 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 Louisville to Midway

Thu, Jan 8 - Mon, Jan 12
Southwest Logo
6:45 am - 7:10 am
SDF
-
MDW
1h 25mnonstop
Southwest Logo
10:00 am - 12:15 pm
MDW
-
SDF
1h 15mnonstop
$171Southwest
Mon, Jan 12 - Tue, Jan 13
Delta Logo
7:50 am - 12:48 pm
SDF
-
MDW
5h 58m1 stop
Delta Logo
5:31 pm - 11:55 pm
MDW
-
SDF
5h 24m1 stop
$174Delta
Mon, Jan 12 - Tue, Jan 13
Delta Logo
7:50 am - 12:48 pm
SDF
-
MDW
5h 58m1 stop
Delta Logo
1:28 pm - 11:55 pm
MDW
-
SDF
9h 27m2 stops
$179Delta
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
6:45 am - 7:10 am
SDF
-
MDW
1h 25mnonstop
Southwest Logo
10:05 am - 5:00 pm
MDW
-
SDF
5h 55m1 stop
$181Southwest
Mon, Jan 12 - Tue, Jan 13
Delta Logo
7:50 am - 6:32 pm
SDF
-
MDW
11h 42m2 stops
Delta Logo
1:28 pm - 8:51 pm
MDW
-
SDF
6h 23m2 stops
$184Delta
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
6:45 am - 7:10 am
SDF
-
MDW
1h 25mnonstop
Southwest Logo
6:50 am - 5:00 pm
MDW
-
SDF
9h 10m2 stops
$186Southwest
Mon, Jan 12 - Mon, Jan 19
Delta Logo
7:50 am - 12:48 pm
SDF
-
MDW
5h 58m1 stop
Delta Logo
1:26 pm - 6:14 pm
MDW
-
SDF
3h 48m1 stop
$191Delta
Thu, Jan 8 - Mon, Jan 12
Delta Logo
7:50 am - 6:32 pm
SDF
-
MDW
11h 42m2 stops
Delta Logo
5:31 pm - 11:55 pm
MDW
-
SDF
5h 24m1 stop
$196Delta
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
11:50 am - 6:50 pm
SDF
-
MDW
8h 00m2 stops
Southwest Logo
6:50 am - 5:00 pm
MDW
-
SDF
9h 10m2 stops
$201Southwest
Wed, Jan 14 - Wed, Jan 21
Multiple Airlines Logo
1:55 pm - 10:32 am
SDF
-
MDW
21h 37m1 stop
Multiple Airlines Logo
1:20 pm - 2:41 pm
MDW
-
SDF
24h 21m2 stops
$216Multiple Airlines
Booking Insights

KAYAK's insights & trends for Louisville to Midway flights

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

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

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

For Louisville to Chicago Midway Airport, Saturday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago Midway Airport back to Louisville, the best deals are generally found on Tuesday, with Monday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Louisville to Chicago Midway Airport, 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 Louisville to Chicago Midway Airport is September, where tickets cost $144 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is $496 and $390 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$67
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 48% lower on average.
Flight from Louisville to Chicago Midway Airport

When to book flights from Louisville to Midway

Are your dates flexible? Find out the best times to travel from Louisville to Midway 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 Louisville to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Louisville to Chicago Midway Airport was $67 for a one-way ticket and $171 for a round-trip.

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

    No, a passport isn't needed to fly from Louisville to Chicago Midway Airport. However, local authorities might ask for an official ID.

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

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

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

    The Boeing 737-700 Passenger/BBJ1 (winglets) is the aircraft model that flies most regularly on the Louisville to Chicago Midway Airport flight route.

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

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

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

    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 Louisville to Chicago Midway Airport.

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

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

    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 Chicago Midway Airport with an airline and back to Louisville with another airline. Booking your flights between Louisville and MDW 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 Louisville to Chicago Midway Airport?

    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 Chicago Midway Airport from Louisville 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 Louisville to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $255 or less one-way and $298 or less round-trip.

Prefer to fly direct from Louisville to Chicago Midway Airport?

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

Direct departures

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

Direct returns

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

Reviews of the top airline flying from Louisville to Midway

 
See real verified KAYAK customer reviews for airlines flying from Louisville to Chicago. 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 Louisville to Midway? 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 4250 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

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

Information on your arrival and departure airports

Louisville (SDF)
Midway (MDW)