Disclaimer: I don't care about image the media has portray of Chicago.
"You know what it is, whenever I visit..Windy city, she blowing me kisses." - Given
Certain songs hit different, and I believe music has the power to influence anyone based on their interests. For example, I love traveling, and when I heard "The London" by Young Thug for the first time in 2020 at a strip club, I instantly connected with the song and became curious about the hotel it referenced. To this day, it remains one of my favorites, and staying at The London hotel in West Hollywood is on my bucket list.
I had a similar experience when I first heard "Chicago Freestyle" by Drake.
Why Chicago?
Despite the negative image portrayed by the media, one track made me curious about windy city. I originally planned to visit in 2022, but the trip was canceled. Fast forward to 2024, I kept seeing "Summertime Chi" on TikTok, and the scenery was captivating. One morning, I checked flight prices and found the cheapest fare I’d seen yet. I decided, fuck it, that's where I'm going for my birthday, and I bought my ticket.
Why solo?
I’ve been wanting to go on a solo trip for a while, but someone would always invite themselves, or I'd get invited on a different trip around the same time I planned to go alone. I also wanted to spend my last birthday in my 20s by myself. I needed time to reflect over the past decade and think about how I want my 30s to be different.
Transportation
According to my research using map apps, most activities were within walking distance from the hotel, except for a few. Initially, I planned to take a Lyft from the airport to the city, but after reviewing the costs, I decided against it. Instead, I did some research on TikTok and discovered that one of the CTA train lines connects directly to the airport for less than $5, look at God.
Once I landed, finding the train station was easy. While I was figuring out my route, a guy who had just gotten off the train turned around and gave me his pass for free, saying it was valid for the next few days. Trusting my intuition, I accepted the metro pass. The train ride into the city took about an hour, and despite hearing horror stories about it, everyone was friendly. Of course, it was daytime, and the Blue Line is known to be safe, only stopping in secure areas. I did switch trains to the Red Line for five minutes before reaching my hotel, but I had heard about the dangers associated with that line, so I made sure to get on and off quickly.
Their train system is very convenient and operates 24 hours. However, be mindful of the lines that run through certain neighborhoods with high criminal activity. I've heard their bus system is great and safer alternative to the train, especially if you're commuting somewhere at night.
Hotel Accomodations
Before choosing a hotel, I made a list of activities I wanted to do, which helped me determine the best side of town to stay on. I also conducted a Google search for the best areas for tourists, with recommendations including The Loop (downtown), Magnificent Mile, and River North. I began searching for hotels on Hotels.com, focusing on one of the recommended areas, and then used maps to calculate the walking distance from various hotels to key locations. After narrowing down my options, I selected a hotel with the best views of the city. However, a few days before my trip, I felt uncertain about my choice, and God reminded me that the site has reviews. After reading the reviews and contacting the hotel to confirm that there was no microwave in the building except for the penthouse suite, I promptly canceled my reservation and booked The Hyatt Place instead. This hotel was within walking distance of two train stations, offered complimentary breakfast, and had consistent positive reviews. I plan to visit again in the first quarter of 2025 and hope to stay at London House, as its rooftop scenery is immaculate and closest to something similar to The London in West Hollywood.
Quick review: Hyatt Place, along with other hotels in the vicinity, automatically locks its doors after 11 PM, and no one can open them without their key cards. Additionally, regardless of the time of day, the elevator won't go up from the lobby until a guest taps their key card. The hotel also had a security officer in the common area every night until the morning. The safety measures were an additional bonus and every staff member was friendly.
Tip #1: Consider the commute to other activities and take the time to read reviews, especially the one-star ratings, before booking a hotel. I also recommend choosing a hotel brand you’re familiar with, such as Marriott or Hilton. Chain hotels tend to have consistent policies and procedures, meaning there are no hidden fees or surprises. If something goes wrong, they have established systems for handling customer complaints and any additionally accommodations. It can be challenging to assess whether you're getting your money's worth if you're unfamiliar with the hotel or if the name is obscure.
Tip #2: The map app on your phone is a reliable tool for calculating commute times and allows you to view the exterior of your intended location. Use your discernment to assess whether the surrounding area seems safe.
Safety First
Aware of dangerous areas. Thankfully, after booking the hotel, I met several visitors from Chicago while bartending at the jazz lounge. They were kind enough to share which areas were safe for tourists, and I confirmed that the neighborhood I was staying in was both safe and walkable. However, they did warn me to avoid the Red Line and to take the bus instead of the train after a certain time at night, as the crime rate is real and the train stations, especially the Red Line, are more prone to violence after dark.
Local support. Two days before my trip, I began feeling anxious about traveling solo to one of the most dangerous cities in the U.S. I reached out to a close friend who has traveled solo before and is also from the Chi. She provided me with an acquaintance's contact info in case I felt uncomfortable going out alone. She also reassured me that I would love the city and offered to connect me with family members for additional support if I needed anything.
Tracker. I shared my location with my mom and one of my best friends, ensuring they both had my hotel and flight information.
A list of convenient lies. When people see you walking alone, they often assume you’re a tourist or wonder why a woman is out by herself. If someone approaches you while you’re walking or enjoying a solo activity, like at a rooftop bar, it’s wise to be cautious and perhaps lie about your name or your reasons for being alone. People can be unpredictable, and answering questions that seem innocent can lead to being vetted as a potential victim.
Commute comfortably. I felt comfortable walking around even at night because the area I chose was walkable, and there were other tourist or locals out and about too. Additionally, police and security officers were stationed outside every hotel and on every block.
Drinking advisory. I returned to the hotel by midnight every night and kept my drinking to a minimum, except for Sunday Funday, I was tipsy by the time the driver dropped me off at the hotel.
Hotel safety. I was also mindful of when to get on and off the hotel elevator. I preferred to ride alone or with another group of women. For instance, one time I entered the elevator at the same time as a male guest. I made sure to control the buttons and, after noting which floor he was going to, I selected two additional floors outside of mine. I didn’t get off until he exited on his floor. Sorry, not sorry—men can be unhinged these days.
Scope the scenery out. After walking around during the day and familiarizing myself with the area on the map app, I gained a sense of the surroundings and identified significant landmarks in case something happened while I was out. With my life experiences and having moved to the city with the highest sex trafficking rates, I’ve learned to be aware of my surroundings.
My recommendations
When should you visit:Â Summer, summer, summer time. Summertime Chi was everything they said it would be and I highly recommend going between May to September.
Hotels:Â Hyatt Place River North | Aloft Chicago Mag Mile | The Godfrey | London House | Arlo | Virgin Hotels | Four Seasons
Attractions:Â Riverboat Tour (can be booked online & nighttime is better), Riverwalk, or Navy Pier | Museum of Ice Cream | Starbucks Reserve Roastry (largest location with 5 stories and alcoholic drinks) | Visit The Bean & Millenium Park | Magnificient Mile
Restaurants: Chemistry | Jordyn's Soul Cafe | The Brunchery | Kitchen & Kocktails
Try the pizza that's what the city is known for.
Surprise, surprise...
I've traveled internationally, to the islands, and domestically, but there's truly no place like summertime Chi.
I'm not gonna yie, I'm strongly considering temporarily relocating to Chicago for the summer and returning to Houston in the fall or before winter begins. I know it sounds a bit crazy, but I felt the same way about Houston and it's been a worthwhile experience. Being young, single, and without kids, I want to explore the world and try everything at least once just to say I did it. My parents and I are praying for guidance (my dad isn't onboard), and I plan to visit Chicago again in March before making my final decision. I also know I’d never move there permanently because I dislike the cold—I'm definitely not built to be Elsa!
Whether I'm in Houston or experiencing summertime Chi, I know it's going to be epic. I gotta do it big before I say goodbye to my hot girl era.
"In the solitude of solo travel, we often find the courage to embrace the unknown and the strength to overcome our fears."
If you enjoyed my review of Chicago, check out my vlog for the vibes and visuals
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