Delta SkyMiles - How to search for low fare flights out of CAK

I am only 4 segments away from achieving gold medallion status with Delta. Being CAK based, I'm looking for a cheap RT ticket sometime between tomorrow and the end of the year but I really don't want to enter dozens of destinations with all of the possible travel dates into the reservation system on Delta's web site. Is there a search engine that would list the lowest fare RT tickets out of CAK for the next 40 days?
Thanks,

Travelocity. Enter the airport codes and select my dates are flexable.

Why not look on Kayak for any flight to a non-Delta hub about three weeks out (not around Thanksgiving or Christmas) to a place AirTran serves? Chances are, that would take care of your four segments.

You could go to Fort Lauderdale December 4-6 for about $250.

Thanks for the suggestions. So far, the best deal I found is for $208, from CAK to MCO on December 4, leaving bright and early and coming back in the evening. I'll keep searching.

Take a look at JFK. Dec 5th $180 with tax in and out same day. It involves some CRJ100 duty.

Take a look at JFK. Dec 5th $180 with tax in and out same day. It involves some CRJ100 duty.

Thanks EVA777,
That's a good deal but I found an even better one. CAK to BWI and back on December 5 for $160 incl. tax. I don't think I'll find anything better than this.
Thanks for all the help and suggestions.

phl in a day via dtw for $160 on dec 5,7,8,9,10,12,14,15,16. also an outbound via atl on dec 5 that will get you 1191 miles before any possible bonuses

I'm CAK-based as well. Just did CAK-DTW-EWR last weekend. Flew my youngest with me for $200 tax-title -out-the-door. That was four segments. It's pretty easy to score inexpensive flights courtesy the Airtran competition.

Went to Manhattan the day of the Yankees ticker tape parade. Penn Station was infested with Yankee fans. But I consoled myself: it's another year closer to the Cubs winning it all!
Was my first visit to the new DTW. That concourse is LONG....!

Still enjoying flashbacks from the trippy tunnel! Almost as groovy as the one connecting the United concourses in O'Hare! XD

Use the following page:

farecompare.com/FlyerTalk

Put CAK in and go.

Use the following page:

farecompare.com/FlyerTalk

Put CAK in and go.

That URL didn't work for me, but http://www.farecompare.com/search/flyertalk.html did.