Where I’ve Been: Quick Trip to Chicago, IL

Hey there! It’s been a while. You may have noticed that there was only one post on the blog last week…typically I aim for 3 posts, and I think the last time I fell short was when I intentionally took time off around our wedding and honeymoon.

The past week and a half just didn’t leave a whole lot of time or energy for blogging. First, I was out in Western Pennsylvania for 3 days at my brother-in-law’s hunting ranch without much cell service, and definitely without wifi (I’ll do a recap post this week!). Then, Adam and I stopped in Pittsburgh for a night (travel guide coming soon!). I got back from Pittsburgh early Tuesday morning with plans to leave the next day for a work trip to Chicago. Well, when that trip got bumped up to Tuesday evening because my Wednesday flight had preemptively cancelled due to an impending snowstorm, my one day to catch up and repack was scratched. And, on the way back from Chicago, I got hit with some sort of terrible bug which meant Thursday and Friday were spent barely functioning.

So yeah…this all resulted in less than an ideal amount of blog work happening.


Since I ended up flying in early to Chicago, it turned my 24 hour trip into 40 hours – not a lot more, but enough that I had a bit more time to explore. I’ve only been to the area once before and I was out in the suburbs. Chicago is definitely high on my list of cities I want to spend more time in, but I was able to get a taste of it last week.

I flew directly from DCA into Midway on Southwest – there are flights pretty much every hour, which made it easy to reschedule my flight when the first one was cancelled.



Since it was a work trip, I was going budget-friendly, and luckily I had a Friends and Family rate through Intercontinental that got me a deal at the Kimpton Hotel Monaco. While I don’t know Chicago at all, this was a quick walk to my company’s Chicago office in (on?) the Loop. I generally stayed within that area and felt totally safe walking early in the morning and late at night.

The decor in this hotel was spot on – as all Kimptons are. Super bright, over the top, so fun. I definitely loved having two nights all to myself in such a quirky place.


I was in Chicago for work, so it makes sense I spent some time working from coffee shops when I wasn’t on-site. I like to get out and about to get work done, because A. I need to grab food anyway, and B. who wants to work from an office or a hotel room?!  The first day I went to Dollop on S. Dearborn Street where I had the most delicious chocolate-orange scone (I’ve been on a scone binge lately). I would definitely recommend this location for cranking through work in a light, bright space with strong wifi.

The second day, I went to Two Zero Three Coffee in the Virgin Hotel. It was way too loud, but the vibe was uber-hip, my lavender matcha latte was delish, and the couple (date?) next to me kept me entertained between emails.



I only had one real meal out while in Chicago since I’d grabbed dinner at the airport on the first night and had lunch with work on the second day (though the bun-taco fusion we had was amazing). I had no idea where to go and felt like I was in a bit of a touristy area, but my colleagues suggested I try out Eataly. I had heard of it, but had never been to one (I believe there are also locations in NYC and Boston), and it was a short walk from my hotel.

For an exhausted meal sitting at a bar, I couldn’t complain. Cheese, cheese, and pasta is exactly what I was craving. My squid ink obsession continued and I’m now thinking all mozzarella should come with a side of spicy pickled vegetables (okay, seriously, I may be going out at lunch to track this down now…Whole Foods will have something similar, right?!).


My hope is that next time I find myself in Chicago I have a little more time to explore the different neighborhoods and go on an architectural tour. I was able to walk around for a bit on Wednesday morning (yup, I got myself up and out the door at 7 AM) and stroll past the bean without another tourist in sight, but I know there’s so, so much more to see. A summertime visit seems like a good idea, right?



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