Chicago Cheat Sheet

There’s one thing that New Yorkers do when they visit a city. They orient themselves by comparing various neighborhoods to the ones from home. I think it’s some weird security mechanism (at least for me) and attempted, while visiting Chicago for the first time. I quickly abandoned these thoughts after realizing it wasn’t what I expected. What makes Chicago special? For me, it’s the architecture and the river that runs throughout the city paired with their well designed public spaces. It’s also one of the very few cities I’ve been to that competes with New York’s diverse and quality food. Last but not least, the people are exceptionally nice. While my trip was brief and sweet, here were 7 spots that made my visit.

My first order of business was to try the local grub. Similar to the endless argument of who has the best “New York pizza” the Illinois capital also has that with its infamous Chicago Dog. After some research I opted for a quick and easy to-go bite at Devil Dawgs. Both locals and tourists seemed to frequent the chain, and it proved to be quite tasty.

My stay was at the beautiful St. Regis. Opened in May of 2023 and designed by architect Jeanne Gang. The shape was inspired by fluorite crystals, towers at a height of 101 floors and is conveniently located within walking distance of Millennium park. It was a delightful stay with stunning views of the city.

If you are able to, snag a reservation at St. Regis’ renowned Tuscan restaurant Tre-Dita by Evan Funke. You can’t go wrong with anything on the menu. My personal favorites were chef’s pastas, which are freshly made every morning, the Tagliata Di Manzo, and the prime 8 oz. ribeye cap which was seasoned and cooked to perfection.

Miru, which is also located inside the St. Regis, gets its own spot on my list because it serves a delicious Japanese Breakfast, a rare treat even in New York. The perfectly cooked salmon with a side of pickles, soup, and rice is something I still think about and would come back for.

While transportation comes easy in Chicago, what better way to tour the town than by boat? If you’re down to venture, try the Chicago River boat Architecture Tour. The 90-minute tour starts at the river walk, which is 5 minutes from the St. Regis by foot and takes you on a lovely ride through the city all the while learning about the rich architectural history of the city. If you don’t have time, a stroll on your own is just as nice!

The Mart, once the world's largest building when it opened in 1930, takes about 2 city blocks. Inside you’ll find just about anything you’ll need, food, shopping, offices, showrooms and more. It’s great for people watching, wandering, grabbing some food, and then sitting down to enjoy.

Last but not least, Millennium park. Have you been to Chicago if you haven’t seen The Bean? After your brief photo op, grab a to-go grilled shrimp salad from Brown Bag Seafood Co. (much needed after your deep dish from the night before), and head across to the quieter and lush Lakeshore East park to eat your healthy lunch while watching dogs play fetch.