The last time I was in Chicago was for AWP, the large national writer’s conference. The time before that was when I was in seventh grade, and our middle school orchestra was invited for an international clinic taking place in the Windy City. Needless to say, I’d never been to Chicago for pure leisure, so you can imagine how excited I was to finally visit Chi-Town for real for the first time in my 30s!

Day 1 in Chicago
  • Lou Malnati’s
  • Avec
  • Blackbird
  • Aviary

Tickets from Houston to Chicago are often cheap, especially during the winter when nobody in their right mind wants to fly to Chicago. Even with already cheap airfare, we opted for the cheapest of the cheap by arriving at a godforsaken hour some time at dawn. Because we arrived so early, we had a long day ahead of us, which translates to more ours to eat!

Lunch was at Lou Malnati’s for Chicago deep dish pizza. Dinner #1 was at Avec, which had come highly recommended by foodie friends, followed by dinner #2 next door at Blackbird. Then we were off for some creative cocktails at the Aviary, sister bar to Alinea.

Day 2 in Chicago
  • Portillo’s
  • Eataly Chicago
  • Graham Elliot Bistro

On the second day, I had to try a Chicago dog. They say Chicago dogs are defined by the diced tomato and neon green relish piled on top. I personally only like diced raw onion on my dog, but when in Chicago…

We headed to the famous Portillo’s for Chicago dogs and Italian roast beef sandwich (another Chicago institution). We digested the heavy lunch at a bar before walking over to Eataly, the mega amusement park, if you will, for lovers of Italian fare.

Dinner was at Chef Graham Elliot’s eponymous bistro; the man himself was in the house and personally cooked up some of the dishes for us. Sadly, GEB has since closed its doors, so I won’t bother with a full review in a later post, but I must say Graham does some pretty cool things with food all the while keeping it real.

Day 3 in Chicago
  • The Publican
  • Shake Shack
  • Girl and the Goat

It’s our last full day in Chicago, and we had a great stay at the Virgin Hotel. (The Virgin adventures don’t end here, though—stay tuned for what happens the next day.)

We have brunch at The Publican before saying goodbye to our friends. Then we share a meal at Shake Shack in the afternoon before heading out to our late reserved seating at Girl and the Goat.

Last day in Chicago

It’s our last day in Chicago, and as always when we’re away from it for more than a few meals, we’re craving Asian food. So we trek it by train out to Chinatown and eat some cheap, comforting Chinese food.

We also encounter additional unwated Virgin Hotel adventures…

Aside from the last event, Chicago was a great food-filled time. Have you been or do you live in Chicago? What do you think are the Chicago institutions one must try on their first visit?

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Discussion about this post

  1. Sham says:

    I love the pizza very much.

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