SUITS+BOOTS

To answer this, I will simply copy and paste my response to canarycoal when she asked something similar of me:

Oh damn, there is so much to do in Chicago. Too bad I am a recluse and have no idea what any of it is.

Seriously though, you’re gonna want to see at a least a few museums. Take a look at this list. I’d highly recommend the Art Institute. It has free admission between 5pm and 8pm on Thursdays. It is right near Millennium Park, which is a cool albeit touristy hotspot. Check out Cloudgate (aka The Bean) there. Another cool thing to do (on a clear day) is to go up to the observation deck of either the John Hancock Building or the Willis Tower (two of the four tallest buildings in Chicago). I think tickets are each around $15.

There are a lot of cool bars in the Wicker Park/Bucktown area along the Blue Line. I’d also highly recommend the Brauhaus in Lincoln Square (take the Brown Line to Western). There are a couple of other cool German bars up there as well. I also really like the Old Town Ale House, near the Sedgwick Brown Line stop.

For food:

Pizza, pan: Pequod’s, Pizza, thin crust: Pat’s pizza or Vito and Nick’s, Chicago dogs: Portillo’s, Gourmet dogs: Hot Doug’s, Burgers: Kuma’s Corner

As far as places to shop, Michigan Ave downtown is where all the stores are. It is pretty terrible because there are always a million people on the sidewalks taking pictures of building with their cell phones. There are a bunch of cool shops on Milwaukee Ave in the Bucktown/Wicker Park area. I’d also recommend checking out Salvage One, very cool.