Frontier: This game animal-focused resto celebrates the most exciting 60 seconds in sports with the standard favorites: mint juleps (with Agave), grandstand champagne cocktails, and country-fried steak. Try on a southern accent while you convince the party in the next booth that your horse is a winner. Brunch starts at 11 a.m., so snag a good seat.
Frontier, 1072 North Milwaukee Avenue (at West Thomas Street); 773-772-4322.
Market Bar: The West Loop's Market Bar won't be left out of the action at the track. We're heading here for amazingly well-priced juleps ($5—dangerous), and a traditional hot brown, an open-faced turkey sandwich with bacon, smoked gouda, and grilled tomatoes. The derby hat contest sounds enticing, too.
Market Bar, 1113 West Randolph Street (at May Street); 312-929-4787.
Bull & Bear: For the third year in a row, Bull & Bear will host its now-famous Derby Days event, and this one's for the high rollers. Place your bets with betting cards available for all guests, and take a shot at wining some luxe prizes like an exclusive Woodford Reserve Kentucky Derby golf bag. Munch on goodies like the Kentucky burgoo stew, the pulled pork sandwich, bacon jalapeno cornbread, and chocolate bourbon pecan bites. Standard southern drinks will be flowing, naturally. Bull & Bear, 431 North Wells Street (at Illinois Street); 312-527-5973.