@bestbuddies: Hi! First, welcome. I am in love with Chicago.
There is TONS to do, but most of my suggestions are to head into the city and explore! Here are some of my favorite spots:
Yolk on Michigan – GREAT BREAKFAST! My fiance took me there the morning after we got engaged and I was in heaven
West Egg Cafe – in “Streeterville” (you’ll learn the ‘areas’ of Chicago soon), awesome breakfasts too!
Giordanos has some of the best deep dish ever. 🙂
Tavern at the Park is a nice restaraunt we like for Friday nights. Older crowd, usually 40+.
Check out the Signature Lounge in the Hancock building on a clear night for a few (overpriced) drinks! But the Signature Room hasn’t impressed me with food.
Sweetwater, Hub51, Quartino’s, and Grand Luxe are all great, lively places.
There are so many little mom and pop joints though. My concentration is usually around Michigan Avenue, but Chicago has many many streets and neighborhoods with all types of crowds.
things to do –
Check out events at the museums!
Football, baseball, hockey!
Ice skating (now) downtown
In the summer you can take a boat tour – those are so fun!
It’s really endless. Think of anything and I could probably find it here.