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What to Do In Chicago

March 30, 2012

Now that we’ve covered what to eat in Chicago, let’s talk about what to do with the few, brief hours when you’re not eating.

The Art Institute of Chicago

It’s considered one of the greatest museums in the world for a reason. The Art Institute has a little bit of everything — from ancient art to modern, Asian to American, famous to ‘huh?’ The main reason I wanted to visit was to see one of my favorite paintings in person:

Un dimanche après-midi à l'Île de la Grande Jatte (

We’re spoiled in DC with our free museums but the Art Institute is worth paying for: American Gothic, Monet’s Water Lillies, Nighthawks, At the Moulin Rouge and Two Sisters (On the Terrace) are just a handful of the incredible works here. Give yourself an entire afternoon — or a whole day — and be sure to make it down to the basement, where a selection of miniature rooms, each like incredibly ornate dollhouses, awaits. I thought it sounded silly but it was actually one of the most fascinating things at the museum.

The Second City

The Second City was home to Steve Carell, Tina Fey, John Belushi, Stephen Colbert, Mike Myers, Catherine O’Hara, Gilda Radner and so many more comedians who are now household names. I’d seen the touring production a few times but this was my first chance check out the real deal in Chicago. We saw The 100th Review on the mainstage and it was pee-your-pants, hold-your-sides funny from beginning to end. Political humor? Check. Raunchy jokes? Check. Gags about midwestern sports teams that I really didn’t understand, but somehow were still funny? Check.

The Bean (Cloud Gate)

If you’re going to be a tourist, go all out and be a tourist.

Impressions from visiting The Bean: shiny from afar, smudged up close. And people are really fascinated by this sculpture, which was only introduced in 2004. No one’s afraid to make a fool of him/herself here — so might as well join in the action.

Wrigley Field

I didn’t actually go in to Wrigley Field but seeing the sign was enough. Mostly because I remember scenes from Rookie of the Year and Ferris Bueller’s Day Off that took place at the park. So — yay sports.

Lake Michigan

A beach… in a midwestern city… in the middle of America.

Mind is blown.

I knew Lake Michigan was big and that my midwestern friends referred to ‘going to the beach,’ but I honestly didn’t know that this existed in the middle of Chicago.

Gorgeous blue water, soft yellow sand — and the Chicago skyline in the background. Not at all what I expected, but at least it explains why Chicagoans stick it out through terrible winters. They have an in-town beach to enjoy once the snow melts.

Of course, one of the best things about visiting a new city is just wandering around and stumbling onto something interesting or beautiful.

Three days in Chicago wasn’t enough time to eat and drink everything the city had to offer — or to spend more quality time with one of my best friends — but it was the perfect amount of time to see the city’s highlights and leave me definitely wanting to come back in the future. So tell me: what did I miss out on doing in Chicago?

Heading back to New York this weekend to hang out with Oprah — more later.


4 Comments leave one →
  1. Life's a Bowl permalink
    March 30, 2012 12:56 pm

    Totally just reaffirmed my wanting to go to Chicago! Def would wanna check out “The Bean,” “The Second City,” and of course Wrigley Field 🙂

  2. March 31, 2012 9:03 am

    It looks like a lovely city!

  3. April 1, 2012 4:15 pm

    I love Chicago and the Bean haha- who cares if it is random? 🙂 I love Second City too. I saw it in Chicago once and then we just saw it in Boston last week.


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