Is Chicago my kind of town?

image: Flicker by ph4nn1 Chicago Skyline Panorama

image: Flicker by ph4nn1 Chicago Skyline Panorama

Last summer I made plans to go to Niagara Falls and Toronto with my kids for a few days. We’d never been and it seemed like a cool and economical getaway. I made hotel reservations and enthusiastically crowd sourced for some tourist recommendations. Then my two older sons got jobs. Plural. Not one to complain about employed children, I cancelled the trip and instead took my youngest down to NYC for a couple of days. That slacker doesn’t have a job, but I suppose he is only 11. Soon enough, little man.

A few weeks after the change in plans, I ended with both a Southwest voucher and a credit on my credit card, a situation which I immediately interpreted as a sign from the universe to buy a plane ticket. I reached out to my posse of friends, a number of whom were also celebrating a milestone birthday this year, to gauge interest in taking a weekend trip somewhere. While there was interest, it didn’t translate into action, so I decided it was time for me to take my first ever multiple night solo – Chicago, here I come!

So, I’ve got three nights in Chicago coming up in a few weeks and I’m a bit overwhelmed by all of the things there are to do! The luxury of traveling alone means I can do whatever I want, whenever I want to, which is pretty amazing. Knowing myself, I see my days being structured kind of like this:

  • Wake up, get out and do something.
  • Go back to the hotel for a nap.
  • Take a run.
  • Take a shower.
  • Go out and eat something tasty.

I imagine there will be alcohol involved, at times, too.

The two things I definitely want to do are the architectural boat tour and an art museum or two. I know there are a million places to eat, but I’m most interested in places where I can eat at the bar.

What can you tell me about Chicago?

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5 Comments

Filed under art, drinking, Eating, ideas, Recommendations, Restaurants, travel, Uncategorized, vacation, Wine

5 responses to “Is Chicago my kind of town?

  1. llcwine

    Incredible Greek food in the Greek Town area…

  2. David Nardolillo

    I assume you have the Art Institute of Chicago on your itinerary. They have a great collection of Monet on permanent display. They also have Edward Hopper’s “Nighthawks” which is one of my favorite paintings. Many good places to eat in Chicago. It really depends on where you are staying and how far you want to roam. If you are want good southern food, and are willing to head up to the Andersonville neighborhood, check out Big Jones. I make a point of always stopping in there for their tremendous brunch, but their other meals are getting rave reviews.

    Other tip: if somebody recommends Tavern on Rush as a good place to eat at the bar, tell them “No thanks.” Safe travels!

    • Definitely hitting the Art Institute! I am starved for some solo time viewing art after spending years being rushed through galleries by impatient children. I love Hopper and will look for Nighthawks. Thanks!

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