The dog: Even though it’s Saturday and you’re not commuting, you’re starting your day with a char-dog with everything at Gold Coast Dogs (222 S Riverside Plaza; 312.258.8585) in Union Station, sporting some of the neon-iest relish you’ll encounter.
The drink: Old Style in a plastic cup from the Snuggery (222 S Riverside Plaza, 312.441.9334), just across the food court area. Snag a table and enjoy them together. Sneer at any strangers judging you for drinking at 10am.
The dog: Walk up Canal St and hang a right on Madison until you hit Wells, then hang a left and you’ll see Westminster Hot Dog (11 N Wells St, 312.445.9514), which makes its own specialty sausages, but you’re staying on-theme and getting another Chicago-style dog (courtesy of Red Hot Chicago). If you MUST be different, you have permission to opt for spicy brown mustard.
The drink: It should be 11-ish by the time you’ve eaten your dog, so mosey on over to Stocks & Blondes (40 N Wells, 312.372.3725) right when it opens. Make like a trader and knock back a whiskey shot.
The dog: Head one block East to LaSalle and hang a left, walk then North across the river until you get to Ontario, and, more importantly, see Portillo’s Hot Dogs (100 W Ontario St; 312.587.8910). Yes, they’re a chain, but they’re a chain for a reason, as they knock out a textbook Chicago dog as well as just about anyone.
The drink: You’re in luck! Portillo’s serves beer, so get yourself an icy goblet of something cold. BONUS POINTS: It might not mix well with the beer, but down a cake shake, too, because, CAKE SHAKE!