Chicago, Illinois - May 2024
What comes to mind when you look back on your friendships? For me, laughter. That's what I remember most about being 14 with my best friend, and what I still get as my 28 year old self. How do you find words when every sight, smell and sound makes your heart soar higher than the skyscrapers you exist so small beneath. Where do you start when a city shows you all of its sides? Chicago gave me everything. This trip gave me all of it.
Only my second cross-state lines trip ever with friends, and they've both been in the same year. All my mind can muster is, why didn't I do this sooner? The deep colored murals and flashes of light and stone wrap the city in warm arms, even on the windy days.. Corinne and I arrive in town first and take the train downtown to our hostel where we rendezvous with Jess, fresh off the plane from O'Hare. No time to waste, we're off strutting through the city and just going where the breeze takes us, and it took us everywhere that week. Millennium park, cloud gate (aka the bean) and the legendary Lou Malnati's greet the day and I could do nothing but eat in this city for the rest of my life. To my fellow New Yorkers, deep dish: it's not "better", but it gives us a run for our money. Thick in personality and saucy, just like my lovely friends, our bellies are so happy.
This city is filled to the brim with history, art and the hippest people. It's not just the street art. Every building, alleyway and city commissioned sculpture is filled with life and a story. Large modern red art pieces are scattered around the city and there's architecture dating from the 20's to today's 20's. While walking through the parks near the water, we came across this little community garden with no fences or signs of ownership. Herbs and spices were being grown for restaurant and communal use. Jess bet me $100 to eat a leaf, so I found the nicest looking piece of mint, along with some dandelion and had at it. For a few seconds I was $100 richer until I returned it. Give me a real challenge.
At one point mid day while in the midst of The Bean, storm clouds come rolling and it's immediately raining buckets. Luckily, I packed an umbrella, which is safe back at the room. We run through the streets looking for both shelter and what will be our next stop. Luckily, Cindy's Rooftop bar is across the street from Millennium Park, but it feels like half a mile with the rain coming down so hard. I'm not sorry about it though. When's the last time I went running through the rain laughing? It's been too long. We head into this beautifully mosaic designed lobby and up the elevator to the top floor. Stepping into the threshold of the bar like a set of wet dogs, we get a drink at the bar and wait for a table. I wasn't planning on it being quite so bougie. Like the kind of bougie where the blue blazer guys have their own "private event" going on in a two by ten ft space 😂We snack on our overpriced hors d'oeuvres and step out to see the view from the balcony. The Bean was closed off mostly, but we got a better view of it from above.
From the minute we got together, there was laughter. Vibing to dance music in an Uber, later that night we head to The Green Door Tavern where one of the best burgers I've ever had awaits me. The Bootlegger has bacon, cheese, whiskey ketchup, a fried egg on a brioche bun and was pure harmony when it met my esophagus, they could've been love interests in the next High School Musical. Part of the reason we ended up at The Green Door was not only for it's historical significance (circa 1921), nor it's retro Playboy pinball machine in which we spent more than a few dollars on; but for one of the city's original speakeasies hiding in the basement, The Drifter. Talk about a hidden door.. you'll have to just see it for yourself. We waited an hour after dinner but it was totally worth it. Your menu is a handful of tarot sized playing cards in this dim, narrow space with a tiny stage. The host outside the front door said something about "performances", but we didn't know what was coming. It was burlesque. Heck yeah. Apparently there's a new performer every hour. We only caught one, but still amazing. This was but one of the espresso martinis I would try while in the city. I'd never had one before now, so there were at least a few in the mix while here. We get a ride back to the hostel and I can't help but sit in awe of the old theater bulbs still shining along the streets and the rays of light on the river coming from the buildings. It's a perfect first day, and it's all about to get even better.
Day 2 brings back the buildings and they're in every color, scale and made of every material from glass to brick. Our day starts at Stan's Donuts where we have the most amazing breakfast croissant sandwiches, hot chocolate which beats Swiss Miss by a mile, and a new invention known as the "cruffin". Half croissant, half muffin. It was glorious. I have to say I was shocked at the level of kindness and customer service in this place. What a joy. Onward we go to Chicago's First Lady, one of the companies offering architecture boat tours along the Chicago River. Our guide knew literally EVERYTHING about these buildings. Not just who built them and when, but everything from family members, their original intended purposes and what they were now used for, details you couldn't even see to the human eye. And she was a volunteer. Bonafede badass is more like it. There were towers and skyscrapers of every color, and as we passed under countless deep maroon colored bridges connecting the city, you could see the cars passing by from underneath almost perfectly. I learned that water taxis are also a method in getting around here.
More than anything, this city is bursting at the seams with history and the passion of the people. One of my favorite spots of which being the American Writers Museum. God what a gem. Not even a gem. It's like that scene in Aladdin when you see the Cave of Wonders. Endless interactive exhibits, written works and stories to be discovered, I've never seen a museum like this. Every single museum on earth should be modeled after this. Locating the "book birds" for a sticker to take home, using every sense to soak in the information and lifetime of the dozens of important writers of our world, inspirational doesn't quite cut it. More importantly, spreading the good word that anyone can be a writer, typewriters are set up so anyone can express their thoughts on the original keyboard in the form of a poem, limerick, or just what's on your mind. All of us were just taken aback by it. Who knows, maybe I'll make it in there one day....
The Billy Goat Tavern is next on our Beanland map and takes us underground thanks to a little silver plaque that looks like the entrance to a subway station. Bring on the Chicago dogs.... rubs hands together menacingly... A simple plain hot dog wrapped in paper lined foil and we load 'em up with pickle slices, (slices, not wedges), mustard, ketchup, onions and relish. You get one of those bad boys with a bag of Lay's and you've made it in life. Wash it down with a root beer or lemonade and your life is complete. Stopping by Devil Dawgs was even better admittingly. A true Chicago dog with a pickle spear, celery salt, relish, mustard, ketchup and tomato, I would eat one of those every single day. The dog was just fresher and you could tell it was boiled and not out of a package. Both methods keeping it simple and delicious. I'll never eat a hot dog without a pickle on it ever again.
As we wander around, there are people of every age, demographic and background that all look like they could be artists. Here, they probably are. Between all of the street musicians, blurred road lanes, J walking and a Palestinian protest we came across, it's a city full of purpose for sure. The city is busy but kind in a way, a sister city of somewhere like New York, but different somehow. At some point we walk past the Starbucks Roastery Reserve and explore the five tourist filled floors where everyone's trying to get their hands on the bar counter where the elevator leads. After a short shared espresso martini flight and a rest at the hostel, we're back out to 360 Chicago, one of the most sought after viewing decks for a perfect view of the skyline. And boy were they right. On the 94th floor, who'd have though a place could look like that. I've been to the top of many-a-building, even the St. Louis Arch, but this was next level. Floor to ceiling windows give you, literally a 360 view that have you stunned once you stop off the elevator. We timed it so we could watch the sun go down over the horizon to catch a glimpse of everything at day, sunset and night hours. We sip on our little red cocktails and I can't look away from where the water meets the land. This is one for the books. We get two nights staying at the HI Chicago Hostel and it's just a big sleepover as we talk and laugh all night about how "you can shower when you're dead", whatever that means.
On day 3, Jess has a early flight, so we have to say see you later for now which always hurts me. At this point, we've seen really everything we set out for, so it's a wildcard kind of day. Greektown makes one of the stops we walk to mid morning and it feels like home once you cross the street into the column, blue and white painted plant pots. It feels like home, especially when we come across a candle shop that's been here for 100 years. It smells like church inside and it feels like I'm back in Queens. We track down Greek Frappe, something I haven't had in a lifetime and sit on this beautiful patio at the Athena Restaurant munching on calamari and soft sesame bread. This place feels like Oasis, especially with the backyard patio. I talk Corinne's ear off about my childhood growing up Greek Orthodox, the food, music, as much as I can remember. Here and throughout the city, there are old neon signs of businesses past and present that take you back in time.
Our final stop brings us to the one and only Concrete Beach, adjacent of the Oak St beach. A, literal, concrete slab that runs for maybe a quarter of a mile from the tip of the sand at Oak St Beach down the water where the jogging/bike paths lead, it's just the kind of weird and interesting place you'd find with amazing views of the skyline and Navy Pier. The city is RIGHT behind you, sand to your right and Lake Michigan in front of you, maybe a foot away. Laying on the cement, feeling the sun, it's crazy to see locals sun bathing in bikinis like it's the middle of June on what to a regular person looks like a parking lot. It's so freaking cool though. There are tons of young people and it's awesome to have found a local spot like this. We walk up and down between the concrete and sand of both areas and it's so nice to smell the lake water. This bright greenish blue is gorgeous, you'd think it was the ocean. People living life with loved ones and kids playing on the sand and in the surf, it's so cool to see. It's just like, BOOM, a beach, out of nowhere. From the street, you can't even tell there's a beach here. One way to enter is through this underpass that looks like a tunnel, and the beach just magically opens up to your right as you walk down the paved pathways. Alas, it's time to rub the sand off my feet and wave goodbye to the city from the orange line, like a friend you hope you'll see again soon.
Chicago, you were everything. Thank you.
Comments