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53 E Randolph St (btwn Wabash Ave & Garland Ct), Chicago, IL
Coffee Shop · The Loop · 316 tips and reviews
Cole Kennedy: Intelli is the truth. This spot is maybe a bit more sterile than their other coffee bars, but the coffee is still impeccable. Go pour over or go home.
Cole Kennedy: Maybe my favorite hotel in Chicago. The view over Grant Park and on to Lake Michigan is stunning, and the concierge lounge takes care of everything. Save time to play some pool in the lobby.
Cole Kennedy: The caramelized onions on the patty melt are thickfreakness. The Sloppy Goat is everything you're hoping for. The Eames chairs will keep you comfortable while inhaling all the food.
Tapas Restaurant · South Loop · 140 tips and reviews
Cole Kennedy: Start your day off right with the Blackstone Benedict (eggs Benedict with truffled hollandaise). Head downstairs and grab Starbucks for coffee, though - $4 is too much for diner coffee.
3145 N Sheffield Ave (btwn W Fletcher St & W Belmont Ave), Chicago, IL
Music Venue · Lakeview · 54 tips and reviews
The Feast: No matter how crowded it gets, there's always a pocket of space near the ramps that lead down onto the front-of-stage floor. Try it, you'll like it!
Cole Kennedy: Secretly, one of the coolest bars in Chicago (if you can find your way through the ship to get there). Order a Dark 'n' Stormy and listen to sailors tell stories.
Seafood Restaurant · Near North Side · 221 tips and reviews
Cole Kennedy: Old school and cozy. Love the vibe. Come in, take a right, and sidle up to the oyster bar. Dare you to break a 6:1 oyster to martini ratio.
Cocktail Bar · Near North Side · 65 tips and reviews
Cole Kennedy: The bartenders here are the coolest, friendliest people. Even if you're not staying at the Freehand, come here and drink. My picks: the Tyler Fry, and whatever the punch special happens to be.
Cole Kennedy: My brain can't process the pleasure I got from this meal. Nancy Reagan should've used these cheeseburgers and fries to keep kids off drugs. Oh, and a chocolate shake. Do it, nerd.
Burger Joint · Fulton Market · 482 tips and reviews
Cole Kennedy: When I think about this place, I make obscene noises. The burger is THAT good. Order the single (which has two patties) with egg and bacon (which is actually pork belly). Add fries. Cry with delight.
Steakhouse · Near North Side · 60 tips and reviews
Cole Kennedy: A transcendent dinner experience. Sublime steaks, perfect sides (get Brussels sprouts), thoughtful wine program, and comforting desserts. Did I mention the swanky atmosphere and world-class service?
Cole Kennedy: It's the perfect date spot. Whether you go before dinner, instead of dinner, or after dinner, you won't be let down. I liked the Midnight Stinger.
2760 N Milwaukee Ave (Milwaukee and Diversey), Chicago, IL
Brewery · Logan Square · 28 tips and reviews
Cole Kennedy: I adore the decór in here. Light and airy without feeling like a soulless cafeteria. Oh, and good beer. There's one that's extra delicious that they make with coffee.
Cole Kennedy: Happy Camper is a good conundrum: It's a near perfect sports bar, but it's also a hip spot with great atmosphere, killer pizza and bar food, craft beer, and a dope soundtrack.
Cole Kennedy: Just like everything else in the Athletic Association, Game Room is too cool for school. It's like your parents' basement, but grown up & swanky. Perfect for groups. (Try their Chicago dog!)
2049 W Division St (btwn Damen Ave & Hoyne Ave), Chicago, IL
Pub · Ukrainian Village · 32 tips and reviews
Cole Kennedy: I need this place in NYC. Or maybe I need to move to Wicker Park? Either way, tremendous food. Highlights include Mulligatawny Soup, Gobi Manchurian, and the Chicken Tikka Kati Roll.
4539 N Lincoln Ave (btwn Wilson Ave & Sunnyside Ave), Chicago, IL
American Restaurant · Ravenswood · 42 tips and reviews
Cole Kennedy: Totally freaking incredible. Do whatever you can to sit at the chef’s counter and order through the whole menu. Highlights include the fried enoki mushrooms, Brussels sprouts, and the raviolo.