Interesting, trying to complete 2 airlines in 1 trip!
Obviously, with the limited number of one-way fares, this is tough to pull off cheaply. I couldn't figure out a way to modify your original itinerary to get a total fare of under $399.
However, I did come up with the following, which is cheaper than that (though more expensive than your original itin) and would get you all the miles you need. As an added bonus, the weather in TPA is probably nicer than ORD this time of year

It looks like you could always come back on the 18th as well if you didn't like the weather for some reason.
$288.30 in US Dollars
1 adult @ $288.30
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This ticket is non-refundable.
Changes to this ticket will incur a penalty fee.
Airport legend:
SDF: Louisville Int'l
ATL: Atlanta Hartsfield-Jackson
TPA: Tampa/St. Petersburg Tampa
ORD: Chicago O'Hare
Louisville, KY to Tampa, FL: 729 miles 6 hrs 21 min
Delta Air Lines Delta Air Lines Flight DL647 on a MD-80 (jet) in coach class
Departs Louisville, KY (SDF) Sat, Dec 17 2:10p 1 hr 22 min
Arrives Atlanta, GA (ATL) 3:32p
1 adult in booking code U, covered by fare (A1) below
Layover in Atlanta 3 hrs 33 min
Delta Air Lines Delta Air Lines Flight DL1016 on a Boeing 767 (jet) in coach class
Departs Atlanta, GA (ATL) Sat, Dec 17 7:05p 1 hr 26 min
Arrives Tampa, FL (TPA) 8:31p
1 adult in booking code U, covered by fare (A1) below
Tampa, FL to Louisville, KY: 1299 miles 5 hrs 41 min
United Airlines United Airlines Flight UA1479 on an Airbus A320 (jet) in coach class
(operated by UNITED FOR TED)
(food for purchase)
Departs Tampa, FL (TPA) Mon, Dec 19 7:29a 2 hrs 46 min
Arrives Chicago, IL (ORD) 9:15a
1 adult in booking code W, covered by fare (B1) below
Layover in Chicago 1 hr 40 min
United Airlines United Airlines Flight UA6832 on a Canadair Reg. Jet (jet) in coach class
(operated by UNITED EXPRESS/SKYWEST)
Departs Chicago, IL (ORD) Mon, Dec 19 10:55a 1 hr 15 min
Arrives Louisville, KY (SDF) 1:10p
1 adult in booking code W, covered by fare (B1) below
Note: You must change terminals in Chicago (ORD).
Booking details
If you want to buy this ticket, it's probably best to use a travel agent (this ticket involves multiple airlines, which can get complicated). If you use a travel agent to buy this ticket:
* If your travel agent is online and has an e-mail address, e-mail this itinerary to them
* If your travel agent is not online, print out this page and fax/give it to them
It is very important to use exactly the same booking codes and fare codes that we've used on this page in order to match the price we've found.
Fare (A1): DL SDFTPA U14NBV fare (rules) $115.81
Tax: US Transportation Tax $8.69
Fare (B1): UA TPASDF WA14AN fare (rules) $115.81
Tax: US Transportation Tax $8.69
Tax: US September 11th Security Fee $10.00
Tax: US Passenger Facility Charge $16.50
Tax: US Flight Segment Tax $12.80
Total for 1 adult passenger: $288.30
(as of Monday, November 28, 2005 3:39pm; fares loaded Monday, November 28, 2005 10:04am)