Last week, I had the pleasure of visiting Chicago, IL, for the very first time. I can genuinely say that I LOVED it! The trip offered the perfect opportunity to visit my best friend – who is currently in graduate school at DePaul University – as well as my friends at K Squared Communications – our public relations partners at Atlas Travel.
I got to experience a delightful mix of touristy things (think John Hancock Center and Navy Pier) and the insider’s guide to places like Lincoln and Wicker Parks (beautiful streets with “L” trains above). Everyone I had ever met from Chicago insisted that I would like it there, and they were totally right.
My biggest takeaways were the food and the architecture. In terms of food, I didn’t take a single bite or sip in the Windy City that I didn’t enjoy. Here are my top picks from my short stay:
- Grahamwich by Graham Elliot – The pastrami reuben was literally the best sandwich I’ve ever had in my entire life. I can’t stop telling people about it. Great atmosphere, and I wanted to try everything on this menu. I will definitely have to go back the next time I’m in town.
- Intelligentsia Coffee – These people take coffee seriously, and the latte I drank was meticulously prepared. Truly an art, super nice people, and unquestionably one of the best coffee experiences of my life.
- Big Star Chicago – I visited on a sunny Saturday afternoon, and the place was packed! People clearly know where to find the best Mexican food in Wicker Park. Their (many varieties of) tacos were outstanding and authentic, they served limeade to write home about, and I openly state that I wanted to swim in that guacamole. So tasty; the perfect match to a warm spring day.
- The Drawing Room – This underground cocktail lounge is super trendy, but don’t be intimidated! The entire staff – from the bartender to the bouncer – was incredibly kind and considerate. They couldn’t do enough for our group during our visit, including complimentary Prosecco to celebrate my friend’s engagement. The food sounded delicious, but this place is known for its cocktails. Skip the beer and ask the bartender to mix you something special.
- Wrigley Field Concession Stand – Yes, some foodies may scoff at this gritty suggestion, but my time in Wrigley was anything but bland. My hotdog – stacked with toppings – was the perfect thing to order at this historic stadium. My Bud Light – which would typically have reminded me of a bad college party – was actually a great accompaniment to the delicious dog, and a refreshing way to watch the Cubs win the game! As a Fenway fan at heart, I’ll always be biased, but I thought this passed the test with flying colors.
In terms of architecture, no single image could adequately express how diverse the buildings are in this beautiful city. Every street has its own personality, as if each structure were an interesting guest at a giant cocktail party. The skyscrapers and apartment buildings downtown act as an incredible and artful backdrop to the river and Millenium Park – perhaps the most famous of Chicago’s many green spaces. Just outside the city, neighborhoods like Bucktown and Wicker Park showcase the deep history of this meticulously planned city, mixed in tandem with the delightful individuality of current homeowners and architects. I couldn’t help but comment with pleasure each time we turned onto a different block!
Do you have any great Chicago tips to share? Favorite restaurants, events or activities that readers should learn about? Please share them in the comments section for everyone to enjoy!