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  • Writer's pictureBryan Jun

goodbye Chicago - part 1 of 3

As many of you know, I'm leaving Chicago "permanently" this Wednesday. As the Windy City was my first home as a true adult post-college and my first real city life experience, I thought that it deserved at least 3 blog posts the reflect my thoughts and feelings. Over the course of the next three days, I'll be discussing:

  1. Things to do and eat

  2. My thoughts on Chicago as a young professional

  3. Personal reflections

Note that while the posts are to serve as a funnel from "objective" to personal, it'll be difficult to detach my subjective opinions from all of the topics mentioned. As a means of background for those of you unaware, I've lived in Chicago full time since June of 2019 following a summer internship the year prior. As the world flipped itself upside down in March 2020, I have gone back and forth between the Second City and Irvine, CA (where my family resides), but I'd identify Chicago as my "home" for the past two years.


Things to Do and Eat in Chicago


For those of you obsessed with the Big Apple that don't consider other cities to be worthy of living in, please note that I actually consider Chicago the best city in America for fun and leisure. This is, of course, taking into account accessibility and cost (which are basically the same thing in 2021). Much of this resides in the fact that Chicago is far cheaper in both activity fees and cost of living as well as its relative size to NYC, which makes all these activities far more accessible without the extensive dependency on a local guide or expensive Uber rides. This list, as always, is not all there is to the topic at hand, but more of a list of "must-do's" if you are in town for 3-4 days. I'm keeping it to five just because it's a good number, but happy to make any other recommendations via email. Also note that this list is purely curated on fun utilization points as it pertains to myself, not a list of things that would guarantee you a full-on Chicago experience or allow you to go home and tell your friends you love the midwest now. It will allow you a couple worthy Instagram Stories, which you probably find more important.


My peers who have visited me will see very familiar names on the list as I tend to bring all the tourists in town to similar places, please don't be offended and remind yourself that you are indeed special.


  1. West Loop / Randolph Street / Fulton - a kind of catch all "thing" to do, but if I listed all the restaurants in this region, it would be an entire list of itself. I'd consider this to be the true "eatery" area of Chicago, which older locals consider ironic because back in the day this was the "bad side" of town. Now, West Loop is known for rather expensive housing filled with young professionals that want both the city vibes while having a false sense of suburban life (there's a playground for kids). Randolph Street has some of (if not the most) the best restaurants in the Greater Chicago Area, inclusive of household names like Au Cheval (this was my first hamburger as an American), High Five Ramen (self-explanatory), Monte Verde (good Italian, not the deep dish kind) and Duck Duck Goat (fusion Taiwanese, I recommend the duck noodles). It's also a great chance to get your Jeni's Ice Cream experience in post-meal. This is not to undermine the number of fun bars in this area that also have a fair share of decent food pairings. Even if you deter a bit from the main Randolph / Green Street area, there's an ample amount of fun eateries and locations, much of which I've never experienced anywhere else. McDonald's "international" location is also here, where pre-pandemic era you were able to try menu items from other countries. Slightly less of a tourist spot, but I'd highly recommend for foodies who are looking for something more than deep dish pizza or Portillo's.

  2. Trump Tower Rooftop Bar - Put your politics aside and trust me on this one, I'd argue it's one of the best views of the city. The best part (and perhaps a well kept secret) is that getting into this outdoors spot on the 16th floor of the Trump Tower is free. If you can set your non-existing city pride aside, you can actually sit here just to have a conversation and enjoy the view in the evening without buying a drink. While the limitations is the view is restricted rather northeast and you're not necessarily at the top of Chicago for an aerial view, there's plenty to see down the river. It's also near perfect for viewing the Navy Pier Fireworks (quite literally straight down the river from where you are sitting), which also occurs free of charge (unless you're paying taxes) every Wednesday and Saturday evenings. If you are looking for a slightly better time, I'd also note that the drinks aren't outrageously priced and while sacrificing for the rowdy college atmosphere that local favorite LondonHouse offers, you're getting the best bang for your buck.

  3. Divvy Bike / Lakeshore Drive / Riverwalk / Navy Pier - The Divvy is Chicago's bike share program, which allows you to easily rent bikes all across the city with easy pickup and drop off at one of the many stations (it now has Lyft integration, which makes the payment and tracking even easier). I'd highly recommend getting one of these bikes, and head on over to Lakeshore Drive, which may be one of the best public spaces the United States has ever created. You can bike from UChicago all the way up to Lincoln Park and more, covering the entirety of what most people would call "Chicago," enjoying the views of the lake and feeling like you're being somewhat healthy (I'll actually say this could be very tiring, so make sure you're not 2 deep dish slices in). The bike rates are nothing compared to the feeling of adventure that you get, which may be rare in 2021 metropolitan areas. You'll also realize the scale of the lake as you ride along the bike path and note it's more of an ocean than a lake (you literally can't see the other side), with multiple beach fronts along the ride. If you're slightly on the less-fit side, Divvy now also offers motorized bikes that allow for an easier ride. I'm kind of cheating here grouping all these together (cut me some slack, it's both water-related), but the Riverwalk is a must. A rather recently completed project, one can walk along the river (which connects directly to Lakeshore Drive as well as Navy Pier) and just marvel at the various buildings along it. The bar "scene" along the river isn't groundbreaking, but there really aren't that many cities in America that offers this kind of majestic view. It's one of those things that you're amazed by every time you partake, and also my favorite spot to get a reaction out of people when I take them for the first time in the evening. It's here where I think to myself, maybe the government isn't all inefficient.

  4. White Sox Game - Could be the most controversial one yet as the residents of Chicago typically like to show their Cubs pride over the Sox, but as someone who's been to both games and no original ties to Chicago, I'd argue that White Sox games are far more fun than its counterpart. It could be 100% because of the fact that I've only been to Cubs games with co-workers for company events and Sox games at my own will, but the passion that Sox fans exhibit far exceeds the Cubs energy. It also helps that the Sox have been killing it this year whereas the Cubs not so much. To make an even stronger case, Cubs tickets are actually far more expensive than Sox tickets, which go for $70-$90 for some of the best seats in the house. Also keep in mind that you're reading the blog of someone that can't name a single current MLB player - which should let you know how exciting these games get. I'll tag along on this one and say that Chicago is a sport hub in general, with access to the Bulls, the Bears as well as the Blackhawks (unfortunately the sports scene at UChicago is practically non-existent, but you have relatively easy access to U Michigan).

  5. Maple and Ash - it's definitely no Alinea, but I'd consider this the best restaurant (considering service, food quality, price, accessibility) and maybe the best "experience" I've had in Chicago. The first time I went was to cash my first paycheck with my colleagues to engage in the ultimate banking hardo behavior, the second to treat my family out for the first time as a full-time adult, and the third was two nights ago as the "last supper" with some of my closest friends in Chicago. Known for their steaks, seafood tower and butter bread, Maple & Ash is what one might deem as the ultimate dining experience. The dimly lit lights paired with the real candles (which are rare these days!) and the surprising diversity of people inside really makes you feel immersed in what it's like to live in a city. I'd highly recommend the "I Don't Give a F*CK" (it's spelled like that on the menu), which allows the chef to bring out a course meal of their choice (it's more than filling and you might have food that you've never had in your life). If you don't go for the catch all, make sure to get the seafood and ice cream towers. Reservations are tight and there's a $100 security deposit per head currently due to COVID restrictions.

I'm seriously going to miss this place, catch you guys tomorrow on the next one in the series.

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