Go to Skydeck Chicago to be on top of the Sears (Willis) tower. This is definitely touristy, but cool if you have never been to the city!
Michigan Avenue, or "The Magnificent Mile" is filled with great shopping and flagship stores. If you walk south (past the river), you will come across Millennium Park where you can snap a selfie at The Bean.
Grab a drink on the rooftop and check out the view of the city! Another favorite rooftop bar of ours is Cindy's Rooftop at the Chicago Athletic Association Hotel.
Pequod's is our favorite deep dish in Chicago. This is definitely a favorite among Chicago natives, and feature beer from a local Chicago brewery (Spiteful Brewing).
West Loop is a great neighborhood with drinks, shopping, and is home to some of Chicago's best restaurants. You can get a drink at Recess, play games at Emporium or Punch Bowl Social, or grab a burger at Au Cheval (pro tip: go early to put your name in, and grab a drink nearby!)