Breakfast: Originally opened in 1923, Lou Mitchell’s is to breakfast and commuters what the Billy Goat Tavern is to lunch and alcoholic journalists. One of the first pit stops along Route 66, it reigns as the king of Chicago breakfasts. Lines can often get so long that patient patrons are served warm donut holes as they wait, but once inside you are greeted with an extra-large menu that covers almost every option known to humankind. Stick with their huge cheesy omelets and tall stacks of pancakes and remember, in true old-school fashion, Lou Mitchell’s is cash only.
Feel like brunch? Every Sunday morning, rain, sleet, or snow, on an obscure stretch of Clark Street, you'll find a crowd gathered in front of a small storefront. All of them are there for one reason: m.henry. Their Sunday brunch menu rotates but stays true to a few cornerstone ingredients: crème and berry-soaked "blisscakes," crab benedicts, omelets drizzled with adobo, and perfect house potatoes. The menu runs the gamut from so tasty you forget it's healthy to so indulgent it's worth another hour at the gym.
Lunch: Here’s the perfect Friday afternoon: skip out of the office, fly into O’Hare, jump in a rental car, and head straight for Hot Doug’s. Don’t worry about this place living up to all its hype – it does and it’s worth the inevitable 30 minute wait. These wieners will blow your mind – and your arteries. Tuck into an elk-bacon sausage covered with cheddar jalapeno, a pork-jerk sausage smothered in queso fresco, a char grilled Chicago style dog, and their famous duck fat fries and you’ll know what so many others know. Only in Chicago, folks, only in Chicago.
Dinner: The Publican is a much-buzzed new joint for meat and beer lovers. As you wait for your table, you have the chance to strategize over the menu – how many pork dishes can you order given the number of people in your party? Plenty. Aside from oysters, and definitely some octopus, how much seafood can you add to that? Go with the three-ham plate, spicy pork rinds, an order of pork schnitzel, and a suckling pig if you’re feeling adventurous (or just hungry).
Drinks: The Violet Hour goes above and beyond the call of duty when it comes to mixing drinks. Their pre-Prohibition specialties contain painstakingly muddled fresh fruit, and they carefully measured liquors so that your fresh fruit gimlet is perfectly mixed and is one of the best you’ve ever tasted. Here’s the deal, though: Get there when they open because once they fill the seats, they don’t let anyone else in. If you’re one of the lucky ones, you’ll appreciate being able to have a conversation where you don’t have to shout over the music while you’re jammed in next to a bunch of drunk frat boys. Can’t find this speakeasy? Just look for the unmarked building with the yellow light above the door.
Hidden Gem: Portillo's is a Chicago chain that's as big as the average Chicago waistline. Not totally gigantic, but not that small either. They're located all over Chicago and throughout the suburbs making this a perfect destination for a family-friendly night out. But despite the theme-park vibe going on, they serve up one mean Chicago-style hot dog. The all-beef dog is salty and robust, making a perfect match for the toppings and poppyseed bun. This is the ideal lunch food people, as long as you only have one. At the location on Ontario you order your grub at one line and then hit up the "bar" (really just a counter) to order some beer while you wait. There's plenty of seating, they have some old-school blues playing, and the AC is cranking--a key to survival in a city that literally melts in the summer humidity.