…when it’s freezing. Any ideas?

Here’s the deal: I’ve been to Chicago several times. I haven’t been THAT impressed with it – so now’s the time to let this city shine. I’m going January 16th or 17th through the 20th (INAUGURATION DAY!!!) so it will be COLD. I know this. When I was in HS, my family and I went to Chicago over Christmas. We had to buy new winter-wear while we were there – including umbrellas. It rained a lot and it was COLD. And it got dark at 4:30. Ugh.

My other high school Chicago experience was a Key Club trip (international convention, baby! wow, what dorks). 🙂 We stayed downtown and were there on a Sunday and nothing was open. We couldn’t find a single place to get dinner. We were frustrated and all declared that we hated Chicago because we had so much free time and nowhere to go!

I went in college and we drove and went to a show at that well-known club that’s down the street or in the same neighborhood as an army surplus/unique stuff store. That was a fun trip because it had a purpose – we were there for a show. We also had a car so we could get around and we went shopping on Michigan Ave…. it was good! (Man I miss crazy spontaneous roadtrips with Kelsey!) 🙂

Post-college, I went to Chicago to visit my same friends that I’m visiting now – but we stayed in Naperville – which was fine with me because all I wanted to do was go to Ikea! (Aaaand hang with my friends.) 🙂 We went to a really fun tapas place and had quality time together and it was awesome.

But now I’m itching for some city time. I want to be amidst the hustle and bustle and I want to experience the CITY. Of course I will be with my friends I’m there to visit and of course I don’t mind experiencing Naperville with them…. but I definitely want to check out what Chicago has to offer.. now that I’m 26 and an adult and into WAY different things than I ever was before. Art galleries? Yes please! Wine bar? Sure why not? Decorating/design stores? Uh huh!

So, here’s the part where you tell me what is a “must-see” in Chicago. (Something more original than Navy Pier, please – UNLESS it has gone through significant changes in the past 10 years). 🙂 I don’t mind doing all the normal stuff, but I want to know “off-the-beaten” path Chicago!