Ah, Chicago! The Windy City. Chi-Town. The Home of the Cubs, the Obamas stomping grounds, and the world renowned Bad News Bears . Don’t come for me Chicagoans! I had big plans for exploring your hood during my last visit but alas, I didn’t come correct… for the second time in a row! However, I am determined to make my third visit amazing once we are safe to move about the country. Here are just a few of the rookie mistakes I have made when visiting Chi-Town in the past. Hopefully, learning from my mistakes will prevent you from looking like a rookie traveler in Chicago in the future.
Rookie Mistake #1: Traveling to Chi-Town during the coldest seasons!
“Nooo…she wasn’t ready.” *Kevin Hart voice* Chicago is such a beautiful city in the fall but boy is it ridiculously cold. During my last trip, the weather was in the 30s with a wind chill that felt like it was actually in the 20s. I believe the weatherman described the conditions as “blustery”. This made doing any outdoor activities quite a challenge. I couldn’t even feel my fingers even with gloves! My first trip to Chicago was cold, windy, and rainy! We spent more time in the condo than we did exploring the city. Take it from me, don’t plan your visit to Chicago during the coldest weekend in autumn or the rainiest month of spring. Locals say its best to visit the city in June & July. Otherwise, you’ll need to layer up accordingly.
Rookie Mistake #2: Trying the deep dish pizza.
Chile listen, I already know I’m going to get a lot of flak for this but just hear me out. *proceeds to clap hands* The deep dish pizza is overhyped. It needed to be said. It is not worth the half hour wasted waiting for it to bake or the hefty price tag. I still remember sitting in Giordano’s at the Navy Pier waiting over 30 minutes for my pizza to be delivered to the table. I was full of excitement waiting to try this infamous Chicago dish. My mom warned me that NYC makes a better pie but I had to try it for myself.
I waited for what felt like an eternity before the waiter finally sat the pizza in front of me. I waited a couple more minutes before digging in because it was piping hot. I took the first bite and what did I taste? Disappointment! It was super thick, oversaturated in sauce, and lacking the cheesy topping I have grown accustomed to. I ate half of the personal dish pie because I really wanted to love it but it was a resounding no for me. Natives agree that Chicagoans prefer the thin crust pizza over deep dish pizza anyway. Uno’s Pizzeria, Lou Malnati’s, and Beggars Pizza were among the top picks to buy some pie in Chi-Town.
Rookie Mistake #3: Letting a taxi driver take me to the Southside after dark.
Y’all where do I even begin? Picture it friends: I had just finished watching the Broadway show, Hamilton, with my hubs at the CIBC Theatre. We were standing outside on the sidewalk in front of the theater. It’s midnight and we were freezing cold and hungry.
We started walking to different restaurants on the block trying to find something to eat. Apparently, everyone else leaving the show had the same idea because the restaurants around the theater packed out quickly. Most eateries ended up having a wait time of 1 hour or more. We could have just ordered something to go but we decided that we should just take a cab and go find food elsewhere since it’s date night.
It’s super cold and hubs is freezing since he failed to pack a real coat to protect himself from Midwestern fall weather because… men. He hailed a cab before we can even figure out where the heck we’re going. We hopped into the taxi going to destination unknown and of course the first question the driver asks is “where to?”
We haven’t the slightest clue. We tell the driver we are looking for good food at a place that’s open late since it’s now after midnight. We asked for area recommendations. Driver says he knows of a few places but they are in his neighborhood, Hyde Park. I’ve heard of Hyde Park because of the Obamas so we’re all like okay cool. Take us to your hood. He seemed like a cool dude. He even offered to turn the meter off and charge us a flat fee in case we decided not to eat there and even agreed to us to bring us back to our side of town for the same flat fee. Sounds like a great deal so we agreed to the terms. We rode for miles from the Magnificent Mile to Hyde Park. Finally, we arrived at the destination.
It’s a club. Imagine my surprise.
I could hear the music blaring. Mind you, we were dressed in business casual attire because we just came from the theater. I’m confused so I proceed to ask, is this a restaurant or a club? He was like both, they serve really good food and they will be open for a while.
I’m looking out the window at the people going in the establishment. They are dressed in clubbing attire. It is clear we would be overdressed and out of place. I was like nah. This is not really what we had in mind. We’re just looking for a nice restaurant without the music scene for a quick bite before we head back to the hotel.
The driver is like “okay cool I got y’all. There is a spot a couple blocks from here that has good food and no music. They should still be open for a bit. They sell soul food.” At this point, any food sounded appetizing because we were so hungry so we told him to take us there.
This is where things go left.
Now we’re riding to restaurant number two. As l look out the window, I noticed that the community gentrification is slowly slipping away with each turn. The neighborhood is starting to look a little rougher. I was like oh crap, we are not in Hyde Park anymore.
We have entered the Southside of Chicago.
I will admit, your girl got a little nervous because my knowledge of the Southside of Chicago is based solely on the documented gang violence I’ve read in news articles and I want no part of that. I asked the driver where we were and how much further until we get to the restaurant. He confirmed we are indeed on the Southside and about two minutes from the restaurant. In that two minutes, I watched some illegal activity take place. Nothing major just a drug deal. I quickly turned my head cause that’s my business and we pull up in the parking lot of the second restaurant.
It’s Harold’s Chicken. I’m in total disbelief.
Don’t get me wrong. I love the occasion fried chicken dinner. I’ve also heard great things about Harold’s Chicken from my friend who is originally from Chicago. But good sir, I am not about to get out this taxi in this sketchy neighborhood for a 3 piece dark at 1 am especially after what I just witnessed moments ago.
I look at my husband and ask are you going in? We checked the scene for safety and there were a group of guys congregating in front of the closed store next door. They were talking loudly to each other. We couldn’t tell if they are just happy to see each other or arguing so we decide to just abort mission.
*insert the long face of disappointment and sounds of hunger here. *
That chicken was smelling so delicious which made me even more hungry. I almost took a chance but we just left location two hungry and a little frustrated. We told the taxi driver that he could turn his meter back on since I felt bad that he went through the trouble and asked him to take us back to our hotel instead.
I think all 3 of us were disappointed at that point. We were so freaking hungry and I’m sure the driver was annoyed we didn’t get food from either of the restaurants he selected. We finally arrived at our hotel and ended up ordering overpriced room service before calling it a night. It was quite the ride to say the least. Friends, learn from my mistake. Always know where you want to go before you hail the cab.
Rookie Mistake #4: Eating at chain restaurants
Chicago is known for its award winning chefs and restaurants. It was even once named Restaurant City of the Year but during both trips I found myself eating at chain restaurants like TGI Fridays and Shake Shack simply for convenience. Now there is nothing wrong with these restaurants, but I usually abide by this self imposed rule: Thou shalt not eat at restaurants found in my hometown while on vacation. That rule went straight out the window due to the weather. These restaurants were close to our hotels so the walk against the wind, cold, and rain was a little more bearable.
In the future, I will be planning my restaurant experiences in advance and taking public transportation if necessary. On my last trip, I did make up for breaking my rule by going to a couple of local spots like the Summer House Santa Monica Restaurant in Chicago’s Lincoln Park neighborhood for a weekend brunch. We also ventured to a cajun restaurant called the Mad Boiler in the West Loop for some New Orleans style seafood. Take it from me, skip Chili’s and opt for some of the amazing dining options found throughout the city instead.
Rookie Mistake #5: Forgoing public transportation
I must admit I never stepped foot on a train or bus during my 2 visits to Chicago. I could have saved so much money on ubers and taxis by learning how to navigate the city on the L or by bus. Most of the downtown attractions are easily accessible by train or bus. Transit Chicago even has a handy downtown sightseeing guide to help you figure out whether to take the train or the bus to popular tourist attractions.
Next time, I plan to just go for it. If I get lost, I will regroup and hop on the correct train to get to my destination . A week long pass for unlimited rides on the train is only $28. I am certain that I paid least 4 times that amount in cab fare and Lyft rides during my 4 day stay on my last trip. Don’t be like me. Save your coins friends. Take public transportation.
What rookie mistakes have you made while traveling domestically or abroad? Have you visited Chicago before? How was your experience? Be sure to leave your comments down below.
Thanks for reading. Stay safe, healthy, and blessed.
