Regarding G&TG - try turning up before the doors open, around 4.30 pm, wait, and get yourself in to the front desk the moment the doors open. The wait will likely be quite decent then. Depends on how many of you there are, a party of two or so is best.
Frontera Grill - ditto, turn up just before the doors open if you have no reservations (they do take a VERY LIMITED number with larger groups and at this date they must be gone). If you sit at the bar you can ord er from both the Frontera Grill menu and the Topolobampo menu.
Are you really sure you want to do Hot Doug's? At 1 pm you could be waiting quite, quite a while in line down the block, for stuff that isn't all that earth-shaking. It's also about 25 miles from Burr Ridge to Hot Doug's, taking Interstate 55 and Interstate 94 along the way, not two of the fastest flowing roads especially on a Saturday afternoon. I'm not sure if there are any major games in town too on whichever Saturday you arrive...
There's a bar opposite Second City but I have no opinion on that one. Not really that much around that area for good dessert & drinks, that I know of anyway. One option might be to head on down to Division, walking down Wells, sampling or eyeing the bars along the way and hitting the Division melee of pubs/bars/general scene (can be a mob around some places) (depends on what sort of clientele you want, too). Or, head on down a little more to Sable
in the Hotel Palomar for fabulous inventive cocktails, one of the largest selections of single malts and whiskeys around, and sample "small plates" (quite good "bar food" IMO although some folks consider the food/desserts from Heather Terhune to be utterly superb [I disagree]). But the drinks and bar atmosphere is bright (can be a little loud), more "upscale", with a pretty nice long bar. The cocktail menu is pages long - plus the listing of the scotches etc, it's a small book!
An alternative is the Violet Hour
(in Wicker Park) on Damen just south of North Ave, 2.3 miles from Second City going west on North Ave. Great cocktails, but no real desserts, there's a selection of cheeses available, also some munchies.
Another option is to wander around Rush & State, just a mile down from Second City (via Clark or Wells) - there are bars and places to grab some dessert around there, loiter around the Viagra Triangle there if you want (heh) and maybe walk down State or Rush (the area can be quite lively) - maybe down to Sable? (Then cab it back to wherever you were parked) :-)
Yet alternatively, you could try out/try for entrance at the Aviary
close by G&TG on Sunday night (if you try for an early dinner) - try emailing them NOW, or just try your luck. They have some of the most inventive drinks around. One of a kind of place. There's not really the same sort of place in NYC (or SF or LA, as far as I know), unless the quality of their concoctions have gone down since I was last there (before their Master Cocktail Maker got kicked out).
p.s. G&TG is Girl & The Goat.
Edited by huiray, 17 January 2013 - 06:35 PM.