Meet Me in Chicago…

I had every intention of checking in from the road last Friday and sharing some photos/stories from my first day-or-so in Chicago- where I spent a few days leading into this past weekend for an impromptu getaway. Of course, anything can happen when traveling- which was pretty much the case when I first arrived in town on Thursday afternoon. With all the airport chaos and confusion, traffic, and looking for late night eats that were within a reasonable walking or driving distance- I simply could not find the time to sit down and write. I was exhausted– and I figured I’d just share it all here today now that I’m back home, rested and recharged, and going through the pictures and videos I snapped along the way!

Troy was (and still is at the time of my writing this) in Chicago for a work-related function/event. With a little bit of time off here and there in-between working and attending scheduled meetings, he’d invited me to come into town to visit and hang out for a few days. Since I still have quite a bit of accrued PTO at my own job to use before the end of the year, and I haven’t been to Chicago in well over a decade- I jumped at the chance for a mini-vacation and flew out on Thursday to meet with him.

After a lot of issues at O’Hare and over an hour of sitting in bumper to bumper traffic- Troy and I reached our downtown hotel to briefly unwind and freshen up (and get fancy -as is our tradition) before we headed out for some much-needed dinner and a couple of drinks. We made reservations at Formento’s– a chic little Italian place in the West Loop. The food and the cocktails were fantastic, and the staff were so unbelievably sweet even as we were finishing up kind of late.

I knew that a good portion of my trip would be spent on my own and exploring the city by myself while Troy worked- and I squeezed in as many activities and destinations as I could while I waited for him to take his designated breaks. On Friday, after getting my morning coffee and walking around the downtown area to get better acclimated with my surroundings- I headed over to the famous Art Institute of Chicago to spend a couple of hours looking at some of the most well-known paintings in the world and immerse myself in the limited exhibit for Barbara Kruger that runs through the end of January 2022.

It was absolutely incredible to see things like ‘Nighthawks,” American Gothic’ and ‘A Sunday on La Grande Jatte’ up close and in-person. I caught myself just looking around in awe multiple times during my stay. It’s such a beautiful museum and a must-visit for anyone looking to spend a few days/a weekend in Chicago!

While I was in the area, I stopped by Millennium Park to see Cloud Gate (the bean!) and grab some deep dish at Pizano’s Pizza & Pasta. The restaurant was lively and clean, but I still don’t get the hype surrounding your pizza, Chicago. It’s just so unappealing. I’m so, so sorry. Thin crust all the way.

On Saturday, my last full day in town- Troy and I went back to The Bean so he could experience it, too- and managed to walk over to Willis Tower where we had expedited tickets to check out the Skydeck on the 103rd floor. I’m not particularly fond of heights- so having the courage to step out onto a glass floor that separated me and certain death was pretty huge. I look absolutely terrified in every photo of me taken while I was out there- but it was huge nonetheless!

Afterwards, when Troy had to return to work- I made one more stop at Wrigley Field just to say I’d been there- and then it was back to the hotel to pack, grab some tacos at Flaco’s Tacos and prepare for my flight home yesterday morning.

I had such a wonderful time, made even more fun and memorable by having been able to spend a lot of it with someone I cherish so dearly. This year has truly been about making up for all the lost trips and travel I missed out on during 2020- and I’m so grateful for the opportunities that have presented themselves this year and so excited to see where I go next.

And since there are still quite a lot of things in Chicago I didn’t have time to see/do- I’m looking forward to returning someday soon!


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Hi! I'm Ashley. I'm a blogger and a radio personality with a makeup and shoe addiction based out of Boston and the Pioneer Valley. These are my (mis)adventures.

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