Justin P.
Google
This place was a pleasant surprise. I found myself in Oakbrook one late evening, looking for a place to have a nightcap. I heard the bar inside the Drake (Polo Lounge) is a classy spot, and the intel was correct. It's not very big, but they have a legit whiskey selection, good service and a decent number of TVs (so if you stop in for a sporting event, pull up to the bar and you'll be fine.) While it was a tad louder than I expected due to the number of patrons, it wasn't impossible to have a conversation if desired.
What really made me happy is I noticed a humidor behind the front bar. I asked the waitress about it, and she confirmed they sell cigars and allow smoking on their patio. Sadly that area isn't heated (which means you'll want to wait for a warm day) but it's a great option for a cigar and a good drink. I didn't try the food, but will put it on the list for my next visit.