Things to Do in Chicago

One of the great things about living in a city like Chicago is the variety -- there is so much to do here, you'll never run out of options. If you're sitting around bored at home, it's your fault. Here are a few ideas I'd like to share, pulled together as my contribution to The MANual: An Experiential Toolbelt for the Everyday Guy. It's far from a complete guide, but hopefully gives you some ideas on how to go beyond the obvious.


Just because you live in Chicago doesn't mean you can't go on a tour every once in a while. You'll learn something new about the city, and it's a great date option because it gives you and your date something active to do and talk about. Here are a couple faves.


I love exploring new cuisines and trying new restaurants. My dad likes to say that you could eat at a different restaurant every night in Chicago and never run out, and he's right. Want to try something new? Pick a country and search for a local restaurant serving its cuisine. From Albanian to Uzbek, it's all here, either in the city or the suburbs. More specifically, here are some tips on where to go for a great meal.


It's easy to have a spirited evening here, and there are plenty of places to do it. These are my favorites.



You know there's at least one team for every major league sport in Chicago, but there are also lots of lesser-known teams and sports worth checking out.

...and so many more. If you can think of it, it's probably out there.

Readings & Shows

Maybe sports aren't your thing. How about storytelling and lit readings? Here's a very small sampling.


The local visual art community is vibrant and active. On the first Friday of the month, the River North gallery district holds open receptions for new exhibitions; on Second Fridays, the Chicago Arts District in east Pilsen holds theirs. These are great opportunities to see new art -- and maybe have a little free wine and cheese, too. ;)

If you're looking to do a movie date, forget the big cineplexes and head to the Music Box or Siskel Film Center. Both play indie films and revivals, Music Box in a beautiful old moviehouse, Siskel in a sleek modern space. Music Box has the best popcorn in the city, while Siskel serves beer and wine. And speaking of, the ShowPlace Icon in the South Loop has a bar and VIP seat-side service in a couple theaters, so you can see that blockbuster in comfort.

For theater, there are so many options. Steppenwolf, Goodman and Lookingglass get all the attention, and it's well deserved, but there are dozens of great theater companies scattered across the city. Some standouts: The Neo-Futurists with their frenetic Too Much Light Makes the Baby Go Blind, The House Theatre, Teatro Luna, and Redmoon's crazy "spectacles."

And of course, Chicago is synonymous with improv. Second City is nice, but a lot of it is aimed at the tourists. Hit iO or ComedySportz in Lakeview or the Annoyance in Uptown instead.