Cheap Flights from Louisville to Chicago
Cheap Flights from Louisville to Chicago
Looking for cheap flights from Louisville to Chicago? 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 Louisville to Chicago 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 Louisville to Chicago for specific travel dates.
2026-11-05
SDF - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-07
SDF - ORD
Economy | Non stop | 2 left
From 4,500 Pts + $25.6
2026-11-08
SDF - ORD
Economy | Non stop | 3 left
From 4,500 Pts + $25.6
2026-11-09
SDF - ORD
Economy | Non stop | 4 left
From 4,500 Pts + $25.6
2026-11-10
SDF - ORD
Economy | Non stop | 5 left
From 4,500 Pts + $25.6
2026-11-11
SDF - ORD
Economy | Non stop | 3 left
From 4,500 Pts + $25.6
Louisville to Chicago 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
Chicago is 1 hour behind Louisville.
Airports in Louisville
SDF · Louisville Intl Standiford Field
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Lexington KY - Chicago · Lexington KY is 62 mi from Louisville
Flights Cincinnati - Chicago · Cincinnati is 84 mi from Louisville
Flights Evansville - Chicago · Evansville is 98 mi from Louisville
Flights Indianapolis - Chicago · Indianapolis is 111 mi from Louisville
Flights Louisville - Madison · Madison is 111 mi from Chicago
Flights Dayton - Chicago · Dayton is 144 mi from Louisville
Premium cabin flights from Louisville to Chicago
Premium cabin
2026-11-11
SDF - ORD
First | Non stop | 2 left
From 16,500 Pts + $10.1
Premium cabin
2026-11-06
SDF - ORD
First | Non stop
From 21,500 Pts + $5.6
Premium cabin
2026-11-11
SDF - ORD
First | Non stop | 2 left
From 30,000 Pts + $5.6
Premium cabin
2026-11-11
SDF - ORD
First | Non stop | 2 left
From 30,000 Pts + $5.6
Premium cabin
2026-11-10
SDF - ORD
First | 1 Stop | 4 left
From 33,300 Pts + $5.6
Premium cabin
2026-11-11
SDF - ORD
First | 1 Stop | 1 left
From 33,300 Pts + $5.6
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
Frequently Asked Questions
The cheapest route from Louisville to Chicago 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 Louisville to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Louisville to Chicago.
Louisville and Chicago 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.
Chicago is 1 hour behind Louisville.
Departures from Louisville: Louisville Intl Standiford Field (SDF). Arrivals in Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD).
Travelers searching this route also look at other popular routes into Chicago, plus the return trip when we track it. Fares and award space change daily.
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