Best View: the Signature Room, on the 95th floor of the John Hancock building, with floor to ceiling windows the view expands over Illinois, Wisconsin, Indiana, and Michigan. Bonus: free entry, just the cost of a cocktail (roughly $15).

Best Entertainment: the Second City, the infamous Chicago improv theatre known for giving us John Belushi, Dan Akroyd, Tina Fey, Chris Farley, Steve Carrell, Stephen Colbert…I think you get the picture.

Best Chicago Dog: Portillo’s and Fat Johnnies. Loaded with the classics: mustard, relish, a dill pickle spear, tomatoes, chopped white onion, celery salt, and sport peppers.

Best Deep Dish: Lou Malnati’s and Pizzeria Uno. If you go to Lou’s, you have to save room for the Chocolate Chip Pizza… a deep dish pizza of creamy chocolate chip cookie with vanilla bean ice cream and whipped cream… ohh, hold on, I’m booking a flight to Chi-Town.

Best Thin Crust: Pizano’s is Lou’s, as in Lou Malnati (see above) son’s pizzeria that serves delicious Chicago pizza, deep and thin crust and very authentic. Get the thin crust though, because you shouldn’t just eat the deep dish in Chicago. The checkerboard-cut thin crust is delicious and a Chicago classic.

Best shopping: yes, the Magnificent Mile has all those main stream shops that every other mall in America has, so try out something more unique and hip, Bucktown and Wicker Park.

Best Time to Visit: those 100 days of summer. The city comes alive in summer with weekends full of festivals and swimming and loads of outdoor eating and drinking. I went in early June and was comfortable in pants and a lightweight cardigan most of the time…the wind is as serious as they say. And the winters are probably worse than you can handle…especially for the outdoorsy tourist.

Those Classic Tourist Spots: make a quick swing by the Chicago Bean (or Cloud Gate, if you want to be accurate) for a photo snap and if you’re feeling adventurous at dodging other tourists, venture out to Navy Pier. Also, Lincoln Park Zoo has free entry and it’s located along the lake.

Less Touristy: grab a Divvy bike and cycle the gorgeous lakefront.

Best Sporting Experience: Obviously, GO CUBS! Grab a sandwich at Lucky’s and head to Wrigley (our favorite seats are the Budweiser Bleachers–the sun & the party is there!).
  
    
    
  
    
    
    
    
    
    
    
    
    

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