Since returning to the Boston area I have fallen in love with cities in a manner I never have before. I can credit this primarily to two things;
1. I was not in a city in Colorado and missed what they had to offer and
2. I discovered the joy of biking in Boston (which really led to just discovering more of what I didn't know about Boston)
There are few cities in the world where I think it is as simple to bike them (relatively) safely as Boston. There are trails and parks, so many squares to explore and, once you figure the route, it's not even a hassle to bike all the way to Concord or to Jamaica Plain - in fact, it's a lot of fun. This biking around though has shown me so much more of Boston than I had ever previously experienced. I'd driven by the Mary Baker Eddy museum before but I had never known there was a beautiful fountain behind it that you can actually walk into (if you don't mind getting a bit damp). And sure there are plenty of places to see the Boston skyline but if you don't experience it from the dock near the Museum of Science and the BU Bridge, you haven't REALLY experienced it.
That being said, I'm here to blather on about Chicago not Boston. Boston is great, but I already live there. I have spent the last few months exploring it and now that the weather is getting colder I find myself biking indoors and taking trips outside of Boston - the most recent being Chicago. And although I didn't bike through Chicago in it's 30 degree weather I did what I probably should have done earlier - really explored the city.
My good buddy Post lives in Chicago and although I'm happy that he's in love, and getting married and moving to sunny Arizona, it does mean that after this past visit I likely won't be visiting Chicago anytime soon so I wanted to make the most of it. I've been there probably fifteen times in the past three years since he moved there and I know all the bars in his neighborhood awfully well. I also know some good BBQ places and I'd explored downtown a bit as well. This time though I went all out and goddamn was I impressed.
Eating -
There are so many food options in Chicago it is almost dumb. I'm talking more options than Boston, better options than NY (yup, I said it). Feeling fancy and want a five hour experience of eating? Go to Alinea (1723 North Halsted, Chicago Illinois 60614, www.alinea-restaurant.com) - Gourmet magazines best restaurant in the country. Twenty-five courses (all a few bites or less) paired with more than ten glasses of wine (not all full sized of course) over the course of an entire night? Insane and exciting as it is expensive. Not want food that you've never heard of? Then gussy yourself up and head over to Spiaggia (980 N Michigan Ave # 2, Chicago, IL 60611) - the favorite of fancy-pants all throughout Chicago. Don't miss the potato gnocci with black truffles but more importantly stay for dessert and get the terrina alla gianduia with a bottle of Birbet - single greatest end to a meal ever.
Not feelin' fancy? No worries, there's even more for you to love. Deep dish Chicago pizza designed to make you fit the role of Chris Farley in an old SNL skit can be found many places but if you only want to get it once go to Gino's East (162 E. Superior St, Chicago, IL 60611). A small serves (at least) two and bring a bottle of white out or a selection of sharpies - for real, you totally won't regret it. Or if you are feeling BBQ head to the unnecessarily lame named but utterly delicious Smoque (3800 N Pulaski Rd, Chicago, IL 60641). Just want a coffee and a scone? The adorably designed Cafe Avanti (3706 N Southport Ave, Chicago, IL 60641) is not to be missed.
Entertaining -
Again, so many choices it almost seems foolish to just name a few but since I don't want to write forever and you don't want to read (me) forever here are the musts.
You must go to a Bears game. Yup, it's that fun. Sure, a pro football game is a pro football game, poor sports on the field and on the stands but the weather is insane here due to the location on Lake Michigan and you can't help but smile and think about the fact that you are watching Da Bears. I guess you could check out a Bulls or Blackhawks game too, but Bears is a must.
You must ride the train all around. Boston has the best T system I have ever seen but all of the best lines are underground and the ones above ground are slow and crappy. Chicago is the opposite - most are above ground and the views tend to be spectacular. Plus the folks are just so much nicer - you can actually start a random conversation with just about anyone and it doesn't seem weird at all. Who said the midwest doesn't have positives?
You must check out Millenium Park and go to the Art Institute. Not only is the Married...with Children fountain in Millenium park but so is one of the coolest amphitheatres ever constructed as well as one of the largest unnecessary but awesome reflective sculptures I have ever seen. The Art Institute (111 S. Michigan Ave.
Chicago, IL 60603) is huuuuge and has a terrific selection of photography right now as well as a Bill Peet exhibit (not to mention countless works of art including but not limited to one well known Georges Seurat you might recognize from a little movie called Ferris Bueller's Day Off.)
What it really comes down to is that every city has something to offer but the difference with Chicago is that it has just about EVERYTHING to offer. Good food, great sports (I didn't even mention the beloved Cubbies), culture, entertainment, friendly folks, good public transportation. There is no good reason to not get to know this city better.
And so although I'll miss visiting Chicago on a regular basis I wouldn't have missed a single trip there for the world. Some of the most fun I've had in my life has been in Chicago - thank you Matt (and Jess) and to a much lesser extent Cooper and not at all to Lucky. Be well.