SDF - MDW

$49 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 10/21. 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

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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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

Tue, Nov 4 - Thu, Nov 6
Southwest Logo
3:20 pm - 9:05 pmSDF-MDW
6h 45m1 stop
Southwest Logo
7:15 pm - 9:30 pmMDW-SDF
1h 15mnonstop
$107Southwest
Find Deal
Tue, Nov 4 - Thu, Nov 6
Southwest Logo
11:45 am - 8:30 pmSDF-MDW
9h 45m2 stops
Southwest Logo
7:15 pm - 9:30 pmMDW-SDF
1h 15mnonstop
$112Southwest
Find Deal
Tue, Oct 14 - Tue, Oct 21
Southwest Logo
11:55 am - 12:10 pmSDF-MDW
1h 15mnonstop
Southwest Logo
12:30 pm - 9:40 pmMDW-SDF
8h 10m1 stop
$113Southwest
Find Deal
Sat, Nov 8 - Wed, Nov 12
Southwest Logo
1:10 pm - 7:05 pmSDF-MDW
6h 55m1 stop
Southwest Logo
8:25 am - 5:10 pmMDW-SDF
7h 45m2 stops
$122Southwest
Find Deal
Sat, Nov 8 - Wed, Nov 12
Southwest Logo
10:45 am - 6:55 pmSDF-MDW
9h 10m2 stops
Southwest Logo
8:25 am - 5:10 pmMDW-SDF
7h 45m2 stops
$133Southwest
Find Deal
Mon, Oct 20 - Fri, Oct 24
Southwest Logo
8:15 pm - 8:30 pmSDF-MDW
1h 15mnonstop
Southwest Logo
9:25 pm - 11:40 pmMDW-SDF
1h 15mnonstop
$134Southwest
Find Deal
Tue, Nov 11 - Tue, Nov 11
Delta Logo
6:00 am - 9:52 amSDF-MDW
4h 52m1 stop
Delta Logo
5:34 pm - 12:06 amMDW-SDF
5h 32m1 stop
$177Delta
Find Deal
Wed, Oct 29 - Wed, Nov 5
Delta Logo
6:00 am - 12:28 pmSDF-MDW
7h 28m2 stops
Delta Logo
5:09 pm - 12:01 amMDW-SDF
5h 52m1 stop
$182Delta
Find Deal
Fri, Nov 14 - Mon, Nov 17
Delta Logo
6:00 am - 9:52 amSDF-MDW
4h 52m1 stop
Delta Logo
10:47 am - 6:54 pmMDW-SDF
7h 07m1 stop
$184Delta
Find Deal
Wed, Nov 12 - Mon, Nov 17
Multiple Airlines Logo
6:00 am - 9:12 amSDF-MDW
28h 12m1 stop
Multiple Airlines Logo
9:27 am - 11:45 pmMDW-SDF
13h 18m1 stop
$203Multiple Airlines
Find Deal

Everything you should know

Top airlines
Southwest
Cheapest • from $107 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
August
Cheapest • 34% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$107
Overall average: $259
Southwest
Tue 11/4Thu 11/6
SDF - MDW • 1 stop
Cheapest non-stop
$134
Typical prices: $214-532
Southwest
Mon 10/20Fri 10/24
SDF - MDW • Non-stop
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 Midway!
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, Tuesday 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 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 August, where tickets cost $186 (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.

Good to know

Low seasonJanuary
Cheapest flight$49
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 26% 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 $49 for a one-way ticket and $107 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 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 $178 or less one-way and $238 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.
8.0
SouthwestOverall score based on 4242 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

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

Information on your arrival and departure airports

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