Pizza pot pie. Yes, you heard that right. Yes, it's worth the hype. We suggest going in the afternoon, and during the week if you come in early, as they don't take reservations and the wait is typically upwards of an hour. They are also cash only.
Hidden inside Restoration Hardware, and just a block from the Claridge House, is one of the best hidden, but not so secret bar/restaurants in the city. They do not accept reservations so I would suggest going early. Don't feel like sitting? Grab a glass of wine and stroll through the 5 floors of RH. On the top floor there is a beautiful outdoor patio with a great view of the city! Just a block from the Claridge House.
Skip the Hancock Observatory and head two floors higher to the lounge! You get the same great views and the only price of admission is a cocktail! Ladies, be sure to check out the restrooms because they have THE best view in Chicago - sorry guys!
If the weather allows, be sure to check out the newly remodeled Riverwalk. There are lots of fun bars and restaurants and the views are hard to beat! Some of my favorite spots include Island Party Hut, City Winery, and Tiny Tapp. Enter near the Merchandise mart on Wells, or any street further east. You can even take the Riverwalk all the way to Navy Pier!