Hard to really say without going through them all. Looking at a frame that I have that has a small selection of my select chips, (30), mostly older acquired chips, I would say,

-Bellagio $10 POKER, Very Colorful and classy
Chip. I love the colors of this chip.

-Paris Jetons. I have the $10 Blue with Magenta
Stripes. That was the nicest I could afford.
The Red and Gold $5 Jetons were also nice but
the nicest that I recall was one that was White
(?) or Light Green with Red and Blue Paris
Logo.

-Bally's/Paris $1 Showgirl. I really like the
quality of the chip. Not that up on the back
side but the side with the showgirl screams the
classic Las Vegas Showgirl theme.

-Being near Valentines Day, I would probably
throw in the 4Q 2000 V-Day chip. This chip
I have always been fond of for the classic
romantic feel of the cupid and the heart...

-$5 Caesars chip that shows an old piece of Roman
Gold(?) with words Caesars Palace. Another
chip that seems well made and well styled.

I don't put any of these in any order as they are only among those that I can think of right now. The 4Q Halloween with Elvira(?) and Roulette wheel design is good. I have a 1997 Penn and Teller that I think is nice. Sigfried and Roy is a good chip also as is a Kenny Rogers from the old Aladdin. I think it was a new years chip. I recall a Flamingo Y2K chip that had a clock on it. I really liked that also. There are some HR chips that I also liked (Santa Clause pictured Below along with Bunny Money) I am drawing a blank on it but there, I think, was a V-Day chip that I got that I liked also. I know I have a few Palms that I can't remember off hand that would be among favorites. Blue Man Group from Luxor and I could go on and on. If I looked through all the chips I have I would probably find others. It would also be difficult to weed them down to only 5.

They aren't chips but I would also say that among my collection that also includes tokens, my 2 favorites would have to be the Treasure Island $1 token that even when worn takes on a cheracter that is very fitting of it's theme. In fact it probably gets better with age as it looks more and more like pirate gold. The other is the Harrah's Tom Sawyer and Huck Finn token depicting the boys whitewashing the fence with Mark Twain in the foreground holding a book. It brings to mind an indirect image of river boats on the Mississippi. The token is not really gambling related but has associations to it that lead to a time and place, a setting...