Chicago, the new age!

I broke my streak of not-so-great New with a trip to Chicago with my guy to visit my best friend. There were so many great moments, but here are my top 5:

1. Piccolo Sogno

Oh my. This was our special NYE date meal, and though it was a spur-of-the-moment decision, it did not disappoint. From our appetizer of grilled calamari (with the suckers still on the tentacles!) to the best ravioli of my life to the 400+ wine list (all Italian!), the meal was perfect from start to finish. I just wish I hadn’t forgotten my camera!

2. The Signature Room

I’m a sucker for good views with visiting a new place, and this didn’t disappoint. Whew.

Hancock Building view from hancock building

3. Jazz Showcase

Though the venue alone would have been by far my favorite place we visited (Miles Davis played there! It’s the definition of a classic jazz club!), the music is what made it extra special.  Roy Hargrove, widely considered the best current jazz trumpeter of the day, killed it with a show that made me melt back into a time of martinis and cocktail dresses. Here’s a great review of the whole thing.

jazz showcase

4. Walking

I adamantly feel that the best way to get to know a city is to get lost in it. Though it was a bit cold for me (read: miserable) so I didn’t explore quite as much as I’d like, the walks were the best part. We wandered into the best little diner, past the Chicago Tribune, and into a dive(ish) bar with a huge selection of local beers on tap. I’d love to go back when I can walk 1/4 of a mile without whining uncontrollably.


5. Breakfast

Orange, Ann Sather, the aforementioned diner, and an Ethiopian brunch made each morning worth walking into those bitter freezing temperatures.


I’d say it was a great trip 🙂