Cheap Flights from Chicago to Louisville
Cheap Flights from Chicago to Louisville
Looking for cheap flights from Chicago to Louisville? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Louisville vary by season, cabin, and date, but available award flights can start around 4,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Louisville for specific travel dates.
2026-11-05
ORD - SDF
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-06
ORD - SDF
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-07
ORD - SDF
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-09
ORD - SDF
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-10
ORD - SDF
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-11
ORD - SDF
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
Chicago to Louisville flight facts
Distance
283 mi
455 km in a straight line
Estimated flight time
about 1h
In the air, for the straight-line distance
Time difference
+1h
Louisville is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Louisville
SDF · Louisville Intl Standiford Field
Nearby airport alternatives
Flights Chicago - Lexington KY · Lexington KY is 62 mi from Louisville
Flights Chicago - Cincinnati · Cincinnati is 84 mi from Louisville
Flights Chicago - Evansville · Evansville is 98 mi from Louisville
Flights Chicago - Indianapolis · Indianapolis is 111 mi from Louisville
Flights Chicago - Dayton · Dayton is 144 mi from Louisville
Flights Chicago - Nashville · Nashville is 151 mi from Louisville
Premium cabin flights from Chicago to Louisville
Premium cabin
2026-11-08
ORD - SDF
First | Non stop | 1 left
From 16,500 Pts + $10.1
Premium cabin
2026-11-09
ORD - SDF
First | Non stop
From 20,000 Pts + $5.6
Premium cabin
2026-11-08
ORD - SDF
First | Non stop
From 21,500 Pts + $5.6
Premium cabin
2026-11-08
ORD - SDF
First | Non stop | 1 left
From 27,000 Pts + $5.6
Premium cabin
2026-11-08
ORD - SDF
First | Non stop | 1 left
From 30,000 Pts + $5.6
Premium cabin
2026-11-08
ORD - SDF
First | 1 Stop | 1 left
From 33,300 Pts + $5.6
Selected hotels for your next stay
Louisville, KY (USA)
The Grady(SLH)
From 72,000 Pts or $184
Louisville, KY (USA)
Hotel Distil, Autograph Collection
From Pts or $175
Frequently Asked Questions
The cheapest route from Chicago to Louisville depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Louisville.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Louisville.
Chicago and Louisville are about 283 miles (455 km) apart in a straight line.
Flying the 283-mile straight-line distance takes about 1h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Louisville is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Louisville: Louisville Intl Standiford Field (SDF).
Travelers searching this route also look at other popular routes into Louisville, plus the return trip when we track it. Fares and award space change daily.
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