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Cheap flights Louisville — Chicago

Louisville (SDF, US) Chicago (MDW, US)
from $102 433 km ~1h 1m 4 flights found 1 airlines cheapest on Wednesday
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $102 on 23.12.2026
Prices shown are from searches by other travellers over the last 24 hours. Missing a date? Click any day — we'll find tickets anyway.
November 2026
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December 2026
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January 2027
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Prices found for 23 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
23 Dec 2026, Wed
Southwest Airlines WN 3819
16:25
SDF Louisville International Airport
17:40
MDW Chicago Midway International Airport
1h 15m Direct
Farera
$102
View this ticket
01 Dec 2026, Tue
Southwest Airlines WN 2350
16:50
SDF Louisville International Airport
18:05
MDW Chicago Midway International Airport
1h 15m Direct
Clickavia
$108
View this ticket
02 Dec 2026, Wed
Southwest Airlines WN 282
03:35
SDF Louisville International Airport
04:50
MDW Chicago Midway International Airport
1h 15m Direct
Clickavia
$108
View this ticket
Route characteristics
Distance
433 km
Flight time
1h 1m
Time difference
-1h
Minimum price
from $102 (23.12.2026)
Average price
$105
Maximum price
$108
Cheapest day
Wednesday
Departure airports (1)
SDF Louisville International Airport
Arrival airports (1)
MDW Chicago Midway International Airport
Airlines (1)
WN Southwest Airlines
Agencies (2)
Farera Clickavia
Prices by day of week
Tuesday
$108
avg $108
Wednesday
$102
avg $105
Cheapest
Airlines — cheapest prices 1
Southwest Airlines
Southwest Airlines
Low-cost 4 flights · 4 days
$102
Where to buy tickets 2
Farera
2 tickets · 2 days
from $102
Clickavia
2 tickets · 2 days
from $108
Airports

From — Louisville (1)

  • SDF Louisville International Airport

To — Chicago (1)

  • MDW Chicago Midway International Airport
Other destinations from Louisville
Nantucket
US
Aspen
US
Atlanta
US · Hub
Balboa
PA
Nashville
US
Baltimore
US
Columbia
US
Chicago
US
Cleveland
US
Charlotte
US · Hub
Champaign
US
Moab
US
Frequently asked questions about the route Louisville — Chicago
How long is the flight from Louisville to Chicago?
Approximate flight time — 1h 1m. This is an average for a direct flight. With connections, the time may be longer.
What is the distance from Louisville to Chicago?
The straight-line distance — 433 km.
How much do flights from Louisville to Chicago cost?
The minimum price over 3 months — from $102 on 23.12.2026.
What is the average ticket price?
The average price — $105. Range: $102 — $108.
What is the time difference between Louisville and Chicago?
The difference — -1h.
From which airports does Louisville operate flights?
From Louisville: SDF (Louisville International Airport).
To which airports in Chicago do flights arrive?
To Chicago: MDW (Chicago Midway International Airport).
Which airlines fly this route?
This route is served by 1 airline: Southwest Airlines.
Are there direct flights?
Yes, there are direct flights. Minimum direct price — from $102. Total direct flights found: 3.
Which day of the week is cheapest?
The cheapest day of the week — Wednesday.
When is the best time to buy tickets?
Optimal — 1–3 months before departure. Check the calendar above — it shows the best dates.
How do I book flights?
Click "View this ticket" on any flight card — you'll be redirected to the booking page with this specific ticket pre-selected.
About the route Louisville — Chicago

Flights Louisville — Chicago is a popular route. The straight-line distance is 433 km. Flight time 1h 1m. Time difference -1h.

From Louisville (SDF) flights depart from 1 airport: SDF. To Chicago (MDW) — 1 arrival airport: MDW.

1 airline operate on this route: Southwest Airlines.

The minimum price for the next 3 months — from $102 (23.12.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $105, ranging from $102 to $108. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Wednesday.

Other destinations in United States from Louisville
Las Vegas
US
New Orleans
US
Minneapolis
US
Miami
US
Memphis
US
Houston
US
Fort Wayne
US
Philadelphia
US

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