“A Day in Series” Chicago, Illinois

You know why I’m here. Deep Dish Pizza and Obama!

Chicago has been on my “list” for a while now as a must-visit US city and this desire only intensified after reading Michelle Obama’s award-winning book, Becoming. I finally was able to make this longing a reality in July of 2019, the weekend of Complexcon Chicago. My girlfriends and I planned a girl’s weekend, centered around some of the events happening at Complexcon, making sure to eat and sight-see our way through the city.

I flew via American Airlines and after a ton of canceled and rescheduled flights as well as lack-luster customer service, I arrived at the Chicago O’Hare International Airport (ORD). This airport is huge and was a bit difficult to navigate, especially when trying to find the ride-sharing pick-up spot to locate my lyft. For some odd reason, ORD has the ride-sharing pickup for domestic arrivals near the domestic departures/entrance.

As I have a friend who lives right on the outside of the city I did not need a hotel and was thankful for this as I was able to save a ton of money. Like San Francisco, hotels seemed to be a bit pricey in the city. If possible, try to either book well in advance or take advantage of options like Airbnb to save on lodging. Staying slightly outside of the city is also an option, especially if when located near a train line.

We rented a car for the weekend and though we were able to find parking for the most part, between street parking or reasonably priced garages, there were a few times we used public transportation and I would highly recommend this. The trains are labeled by color, green line, red line, orange line, etc. and there is also a bus system to help navigate the busy city streets. A one-way train ride cost us about $2.50. We got a train pass that we were able to load up as needed. These can be easily purchased at any train station. Lastly, google maps is a great way to navigate the city and the trains for those unfamiliar.


Literally, my first stop in Chicago-Giordano’s Pizza, in their downtown location. Living in NYC for the better part of my adulthood, I know good pizza and as a call to the “who has the best pizza” debate, I had to weigh in with my opinion. I love NYC but Chicago might have this one. I normally shy away from the super touristy food spots, but Giordano’s lived up to the hype for sure. A group of 4 of us ordered 2 medium pies (one veggie for myself and a friend and a meat-lovers for our carnivore friends) and we both had more than half of our pies to take home and indulge in later. The deep-dish pizzas do take about 45 minutes to make so keep this in mind and there are several Giordano’s locations throughout the city.

Chicago’s Home of Chicken and Waffles Delicious southern-style food with a friendly wait-staff and great prices. I ordered the “Aunt Joyce” and it came with a choice of dark or white meat chicken, 1 waffle, 2 eggs, and a choice between rice or grits, all for less than $20 bucks. This restaurant is located in Oak Park.

Batter and Berries– This seemed to be the number one recommended brunch spot when I asked friends who’ve been to Chicago before, and I understand why. “Home of the world-famous French toast flight”, B&B serves your traditional brunch menu plus more, adding their own spin on breakfast. Being so popular, the wait was long and they do not accept reservations. Instead, you can add yourself to their waitlist on Yelp.

Garret’s Popcorn-If you haven’t heard of this place you need to be sure to add it to your list anyway. Growing up I always had older cousins who ate Chicago mix style popcorn so I was a little too hype to get to Garret’s and order a “Chicago Style” small bag! Probably the best $5 spent on the entire trip! Chicago style is an equal mix of cheddar and caramel popcorn and Garret’s flavors were pungent and full!

Uncle Joe’s Jamaican Spot in Hyde Park– We randomly stumbled upon this gem and I’m so glad we did. Serving your traditional Jamaican cuisine, there were various platter options to choose from. I ordered the Jerk chicken dinner and water and paid less than $15! I have a knack for authentic tasting food and Uncle Joe’s hit the nail on the head.

Chicago is apparently known for its hot dogs. I don’t eat beef or pork and could not find a place that served turkey or even vegan hot dogs. Just to see what all of the hype was about I did get a beef hot dog from a local cart, outside of a nightclub, and it was good! They added grilled onions and a hot mustard with a traditional hot dog bun all for $5 bucks.

Night Life

Apogee Lounge– Cute rooftop lounge in downtown Chicago, serving specially curated drinks and a view. My girlfriends and I each ordered one of their signature cocktails and they did not disappoint. I had the Nymph and it was super refreshing without being overly sweet!

Here is an additional list of fun/hype nightclubs, bars, and lounges that we visited while in town: Prysm, Y Bar, Persona, Underground, Reverie, Promontory

My girlfriend over at Brooklyn Mavens (IG @bkmavens)  and I had an entire itinerary planned out, making notes of the key spots we wanted to see while visiting.


Complexcon-  Clearly, I’m not in touch with the culture because I had no idea what to expect, but that’s exactly what I got, culture! A not-so-secret sneakerhead meet up with guest appearances, musical performances, and a chance to check out throwback sneaks and what’s up and coming. We purchased our Complexcon tickets a few months before our trip and paid $100 for a 1-day pass for Saturday. I enjoyed myself so much, getting to see Spice Adams, Allen Iverson, Ella Mai and more! I also tried to purchase a new pair of sneaks but clearly, I’m still a rookie here and need to do a bit more research.

Shoreline Sightseeing Boat Tour– We went to the Navy Pier (where we also got our Garret’s Popcorn) and purchased tickets for the classic lake tour. Shoreline offers many options from water taxis, the classic lake tour we opted for our other extended tours including longer rides and more intensive history lessons. We paid $23 dollars and rode along Lake Michigan for 40 minutes learning more about the lake, the city of Chicago and a bit of US history. There is also a bar onboard or you can purchase beverages at one of the local stands before boarding. If you’ve tuned in before, you’ll know that I love the Hop On Hop Off Bus Tours when visiting a new city, and though Chicago does have that option, seeing the city from a boat with a drink in my hand seemed like the obvious choice. If you have time for both, definitely do so!


Cloud Gate (The Bean)– Public sculpture in the center of the Millennium Park Plaza and one of the top tourist attractions in Chicago. This iconic Chi-Town symbol is going to be completely packed with visitors unless you can get yourself up super early in the morning to beat the crowds, regardless, it’s worth the visit to the most photographed Chicago location. Definitely, use public transportation to get here as parking might prove to be difficult.


Willis Tower Skydeck (Sears Tower)- Want to get a nice view of the entire city? Visit the 103rd floor of the Willis Tower! We actually did not end up making it here because of the weather. It rained on our last day in town and I was told that the views were not worth it if the weather was not cooperating. Though I was disappointed to miss it on this visit, I got amazing views of Chicago on the boat sightseeing tour as well as on the many rooftops we visited.

The 16th Annual Sound System Block Party–  On our second to last day we heard that the city would be having their largest block party in the Hyde Park area and decided to go. By the time we got there, after Complexcon, it was completely packed. Assuming folks wanted to wait out the hot weather and come outside after the sun went down, it was impossible finding parking, it was uncomfortable walking the streets and overwhelming with everything going on. Still, it was cool to see something as large as this as I don’t believe I have before. The event is organized by The Silver Room, a store mixed with mainly locally sourced jewelry, accessories, clothing and more. If you’re ever in town during the block party definitely check it out, grab a drink and shop with local vendors! Get there early and don’t drive!

An extended weekend is definitely enough time to get a “taste of Chicago” and explore a good chunk of all the city has to offer. Unlike prices in other big cities like Boston, NYC or LA, I feel I came in way under my budget for Chicago. Figuring out the best time to visit will be the biggest deciding factor as the city sees below freezing temperatures in the winters and experiences smoldering heat in the summers. The temperature averaged around 95 degrees (feeling like 103 most days) during our visit, I literally sweat out my edges and through my white tee-shirt, but enjoyed myself none the less.

Cream Beach Photo Pinterest Graphic (7)

One Comment on ““A Day in Series” Chicago, Illinois

  1. Pingback: In the midst of COVID-19, when can I start traveling again? – Weight Loss. Travel Gains

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