SDF - MDW

$89 Find Cheap Flights from Louisville to Chicago Midway Airport - 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 Louisville to Midway departing on 8/5. 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
$177
Typical prices: $275-$97
Southwest
Wed 8/26Wed 8/26
SDF - MDW • Non-stop
Cheapest one-way
$89
Southwest
Wed 8/5
SDF - MDW • Non-stop
Top airlines
Southwest
Cheapest • from $177 (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 14m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
February
Cheapest • 100% 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

Wed, Aug 26 - Wed, Aug 26
Southwest Logo
1:15 pm - 1:30 pm
SDF
-
MDW
1h 15mnonstop
Southwest Logo
6:20 pm - 8:35 pm
MDW
-
SDF
1h 15mnonstop
$177Southwest
Wed, Aug 26 - Wed, Aug 26
Southwest Logo
1:15 pm - 1:30 pm
SDF
-
MDW
1h 15mnonstop
Southwest Logo
3:05 pm - 9:30 pm
MDW
-
SDF
5h 25m
1 stop
$187Southwest
Wed, Aug 26 - Wed, Aug 26
Southwest Logo
8:45 am - 9:00 am
SDF
-
MDW
1h 15mnonstop
Southwest Logo
2:00 pm - 8:35 pm
MDW
-
SDF
5h 35m
2 stops
$192Southwest
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
1:15 pm - 1:30 pm
SDF
-
MDW
1h 15mnonstop
Southwest Logo
7:50 am - 10:10 am
MDW
-
SDF
1h 20mnonstop
$196Southwest
Wed, Aug 26 - Wed, Aug 26
Southwest Logo
5:30 am - 9:00 am
SDF
-
MDW
4h 30m
1 stop
Southwest Logo
10:10 am - 8:35 pm
MDW
-
SDF
9h 25m
2 stops
$202Southwest
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
5:30 am - 9:00 am
SDF
-
MDW
4h 30m
1 stop
Southwest Logo
7:50 am - 10:10 am
MDW
-
SDF
1h 20mnonstop
$206Southwest
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
7:05 am - 3:25 pm
SDF
-
MDW
9h 20m
2 stops
Southwest Logo
7:50 am - 10:10 am
MDW
-
SDF
1h 20mnonstop
$211Southwest
Thu, Sep 10 - Mon, Sep 14
Southwest Logo
7:10 pm - 7:25 pm
SDF
-
MDW
1h 15mnonstop
Southwest Logo
8:00 am - 10:25 am
MDW
-
SDF
1h 25mnonstop
$215Southwest
Sat, Aug 8 - Wed, Aug 12
Delta Logo
7:55 am - 12:39 pm
SDF
-
MDW
5h 44m
1 stop
Delta Logo
9:24 am - 1:51 pm
MDW
-
SDF
3h 27m
1 stop
$216Delta
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
7:05 am - 3:25 pm
SDF
-
MDW
9h 20m
2 stops
Southwest Logo
6:05 am - 3:10 pm
MDW
-
SDF
8h 05m
1 stop
$221Southwest
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.

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

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

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 Wednesday is the most expensive. Flying from Chicago Midway Airport back to Louisville, the best deals are generally found on Thursday, 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 February, where tickets cost $0 (return) on average. On the other hand, the most expensive months are June and May, where the average cost of round-trip tickets is $373 and $337 respectively.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$89
Best time to beat the crowds with an average 51% drop in price.
Most popular time to fly and prices are also 51% 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 5 days, the lowest price for a flight from Louisville to Chicago Midway Airport was $89 for a one-way ticket and $177 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, Delta, JetBlue, and Alaska Airlines 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 Embraer 175 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 $203 or less one-way and $385 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 4235 reviews
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
Airline reviews

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!

10.0 ExcellentAnonymous, Jun 2026
OKC - LAS
Read more Southwest reviews

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.

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.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

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

Information on your arrival and departure airports

Louisville (SDF)
Midway (MDW)