SDF - MDW

$39 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 8/4. 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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Flights 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, Aug 7 - Mon, Aug 11
Southwest Logo
7:10 pm - 7:30 pmSDF-MDW
1h 20mnonstop
Southwest Logo
10:00 am - 12:20 pmMDW-SDF
1h 20mnonstop
$77Southwest
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Thu, Aug 7 - Mon, Aug 11
Southwest Logo
7:10 pm - 7:30 pmSDF-MDW
1h 20mnonstop
Southwest Logo
5:10 am - 12:30 pmMDW-SDF
6h 20m1 stop
$87Southwest
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Thu, Aug 7 - Mon, Aug 11
Southwest Logo
1:15 pm - 1:30 pmSDF-MDW
1h 15mnonstop
Southwest Logo
11:10 am - 6:35 pmMDW-SDF
6h 25m2 stops
$92Southwest
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Thu, Aug 7 - Mon, Aug 11
Southwest Logo
4:20 pm - 10:00 pmSDF-MDW
6h 40m1 stop
Southwest Logo
11:10 am - 6:35 pmMDW-SDF
6h 25m2 stops
$102Southwest
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Sat, Aug 9 - Mon, Aug 11
Southwest Logo
6:35 am - 6:50 amSDF-MDW
1h 15mnonstop
Southwest Logo
10:00 am - 12:20 pmMDW-SDF
1h 20mnonstop
$114Southwest
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Tue, Nov 11 - Tue, Nov 11
Delta Logo
10:15 am - 12:32 pmSDF-MDW
3h 17m1 stop
Delta Logo
5:25 pm - 11:56 pmMDW-SDF
5h 31m1 stop
$177Delta
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Sat, Aug 9 - Mon, Aug 11
Delta Logo
8:05 am - 6:40 pmSDF-MDW
11h 35m2 stops
Delta Logo
12:43 pm - 6:40 pmMDW-SDF
4h 57m1 stop
$182Delta
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Mon, Jun 30 - Fri, Jul 4
Delta Logo
12:44 pm - 5:40 pmSDF-MDW
5h 56m1 stop
Delta Logo
1:09 pm - 9:13 pmMDW-SDF
7h 04m2 stops
$204Delta
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Thu, Jul 24 - Fri, Jul 25
Allegiant Air Logo
5:43 pm - 8:22 amSDF-MDW
15h 39m1 stop
Allegiant Air Logo
2:54 pm - 10:04 amMDW-SDF
18h 10m2 stops
$276Allegiant Air
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Thu, Jul 17 - Fri, Jul 18
Allegiant Air Logo
5:43 pm - 8:22 amSDF-MDW
15h 39m1 stop
Allegiant Air Logo
10:31 am - 10:04 amMDW-SDF
22h 33m2 stops
$298Allegiant Air
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Useful Info

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, Wednesday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Chicago Midway Airport back to Louisville, the best deals are generally found on Saturday, 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 January, where tickets cost $197 (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.

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Good to know

Low seasonJanuary
High seasonOctober
Cheapest flight$39
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly and prices are also 10% 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 $39 for a one-way ticket and $77 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 $209 or less one-way and $341 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 4278 reviews
8.0Comfort
8.6Crew
8.2Boarding
7.6Entertainment
7.1Food
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

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

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

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

Information on your arrival and departure airports

Louisville (SDF)
Midway (MDW)

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