A Weekend on the Magnificent Mile

As embarrassing as it sounds, before last weekend the only association I made with Chicago was Michael Jordan. Yet funny enough, I didn’t even get a chance to see his iconic statue outside the United Center – because there were many other things to enjoy in this wonderful city.


After a 9-hour drive from Toronto, the first thing that I noticed as we pulled into the Windy City was the cleanliness of the streets. No garbage lying around and minimal litter, but instead elegant lamp posts, mini garden patches and relatively smooth tiling on the sidewalks. The subway system, though less clean, is a step up from that of Toronto in that it is more extensive yet not overly complicated.


City Attractions

In the midst of all the tall buildings and shopping venues along Michigan Avenue is Millennium Park, a central hangout that features live events every Friday and attracts tourists to its renowned work of art, The Bean. Admittedly, I couldn’t resist taking several clichéd selfies in this gigantic monstrosity for a mirror.


As the weather held up, we also visited the Buckingham Fountain at Grant Park and took a nice long stroll along Navy Pier, both beautiful attractions in their own right.



If you want convenient access to the biggest fashion brands, then take a walk down the Magnificent Mile. Most brand name stores have multiple floors and you can easily spend hours browsing through the variety of selection available in a single store. Surprisingly, after spending hours in Nordstrom Rack and the flagship Nike store, I came out with nothing – but only because I was able to remind myself I didn’t really need anything. Had I stayed in the city for longer than three days, I’m sure this would be a different story.



Delicious is an understatement to describe how good the food was. A review of all the amazing restaurants at which we dined can easily be a blog post on its own. From the appetizing delicacies at The Purple Pig to the double cheeseburger (which turned out to be a triple cheeseburger) at Au Cheval to my first taste of deep-dish pizza at Lou Malnati’s to our take-home souvenirs from Garrett Popcorn, there was not a single meal that was not worth the wait. It’s not uncommon to have to wait over two hours in line for a seat and that’s with reservations, but it speaks to the high quality of the food. From a business and marketing perspective, each of these restaurants simply focuses on doing one or two things really well and that’s it. Their investment into perfecting the taste of their dishes rather than pursuing aggressive expansion has earned them a unique aura of scarcity, effectively increasing customer demand, especially from first-timers like myself. As a result, the very feeling of exclusivity and word-of-mouth that spreads is all the marketing they need.


Other Attractions

Some of our other adventures included an early visit to the John G. Shedd Aquarium and drinks at the Signature Lounge on the 96th floor of the 360° Chicago building (formerly the John Hancock building), where a great view of the city can be seen.


I was also personally fascinated by the Rock ‘n’ Roll McDonald’s flagship location, which features the iconic Golden Arches as part of the building’s architecture and an upstairs McDonald’s Museum detailing the evolution of the fast food chain throughout the decades.


Oh and this place that I only saw from outside given that it is out of my league.


But that’s ok because next time I will make it a point to visit His Airness (that is to say, his granite replica).


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