Back in August of 2008 (when I was 26-years-old), I wrote a post on here titled Chicago on my mind. It was short and sweet and this is what it said:
I can’t decide whether I am caught up in the moment, or whether I’m actually having a revelation. After spending a weekend in Chicago, I am all consumed (again) with the idea of moving there. After my first visit a couple of years ago, I declared Chicago to be my favorite city in the world. In fact, it inspired me to move out of Charlotte and while in my quest to score a job in the Windy City, I landed short and ended up in DC. And although I’ve loved living in DC, I’m realizing that my crush for Chicago is back to get me!! It’s amazing how much this feels like being in love. I haven’t been able to think of much else.



My wish did came true in 2010 when, freshly wed, I moved-in with Devang on the 11th floor of the Sandburg Towers in the Gold Coast neighborhood. What an amazing time of my life it was! Chicago quite literally forged a new identity for me that among other things, included becoming a mother. Basically, I haven’t fallen so hard for a city like I did for Chicago, not even Paris.


Today, tuesday April 7th, is when we were suppose to leave for a week-long vacation to Chicago. The last time we visited was in December 2017 (you can read all about it here). I am saddened knowing that we will have to wait even longer now.

To cope with my despondence, I thought it would be nice to share some local insights having lived there for a while.
- First up – Yes, take the L from the airport into the city; the blue (O’hare) and the orange line (Midway). It’s cheap. It’s quick. It’s completely doable with kids and strollers. If you are coming from a city that doesn’t have public transportation especially, this is your chance to experience the amazing benefits of being well connected without ever having to drive.
- Chicago is the birthplace of great architecture. If you are traveling without kids, an architectural tour (either via boat or walking) is a MUST. Even with young kids, I suggest bringing the stroller and spending as much time as possible just walking around. My top five favorite Chicago buildings that you mustn’t miss: 875 N. Michigan Ave formally known as the Hancock Tower (have coffee or dessert in the Signature Lounge restaurant on the 96th floor; preferably at night), Carbon and Carbide building, the Marina City Towers, Wrigley Building, and the Chase Tower where I once worked (this is where NPR’s Wait Wait Don’t Tell Me … is tapped, it has a huge Chagall Mosaic in the courtyard with a fountain; the food court inside is an excellent option to grab a bit). In short, DO NOT LEAVE CHICAGO WITHOUT LEARNING ABOUT IT’S ARCHITECTURAL HISTORY. DO NOT DO IT.
- Go see Millennium Park no matter what the weather. It isn’t just for tourists. The Cloud gate (unofficially known as the Bean), Crown fountain, Maggie Daily Park, and so much more). Ideally you’d spend an entire day just hanging out here, but if the weather is not on your side, still try your best to walk around to admire its beauty). Look up their schedule of events before hand because in the warmer months there is always a performance or a festival going on.
- Walk around Gold Coast neighborhood at night. Be as snoopy as legally possible as you peer into the beautifully lit and decorated homes. Observe the night life and people watch.
- If you are a visitor in Chicago, chances are good that your hotel is somewhere in or near the LOOP. It is the most convenient after all. Here are two destinations worth venturing out to with the help of the train (might take a while), or an Uber (quicker): Garfield Park Conservatory and the 606 Trail.
- Another MUST in Chicago is to eat at one of the many Rick Bayless restaurants. XOCO on North Clark Street being one of my most favorites.
- Some of my favorite Chicago hotels: Virgin Hotel, The Langham, The Peninsula (they also offer afternoon tea service), Loews Hotel (especially with kids), 21C Museum Hotel (if you love the idea of staying in a museum). Logan Square, Wicker Park, and Gold Coast are some fun neighborhoods to be in.
- Public art is at its best in Chicago. Picasso, Chagall, Calder, are just some famous artists who have left their mark on Chicago. In fact, you can show up in Chicago dead broke and still have a fabulous time just walking around and enjoying what’s for free.
- Have a picnic in one of the many parks, hang out at one of the beaches on the lake, rent a bike. Google what farmers’ markets are on during your visit and plan to visit them for breakfast or lunch.
I already feel better having shared this with you. The archives on the sidebar over there have many more posts about my life in Chicago circa 2010 – 2015. Most of it is mundane but as any past record, it is evidence of a time spent growing and exploring new things. I hope you get a chance to see them.
And to you Chicago, I hope to see you soon. Stay well.

Chicago misses you and I do too! I’m bummed this trip was canceled but I look forward to seeing you when you do get here again in the future. 💜