Although I’ve spent most of my life in the south, I was born in St. Louis, Missouri. I spent my younger years in Southern Illinois, and as long as I lived in the Midwest, I never made it to Chicago. Crazy, right? Well, I took advantage of the Fourth of July holiday and finally explored the city with one of my dearest friends. Chicago is the perfect blend of metropolis and middle America. Wholesome, but not out of touch. Bustling city with the friendliest people. It was the perfect place to celebrate all things America…
After meeting up with Victor in Indianapolis, we drove to Chicago and checked into our hotel on Michigan Avenue. Shoutout to friends in the hospitality industry because we got the hookup with an amazing suite and an incredible view of the city. After settling in, we took a stroll to the Hancock Building and zoomed 96 floors up to the Sky Lounge. We enjoyed a drink at dusk and admired the beautiful city from what felt like a cloud in the sky. It was an incredible introduction to Chicago.
Over drinks, we made contact with an FSU alum and friend, also named Amy, who lives in the city now. We were immediately stoked to catch up and take the lead from a local. She gave us a tour of her Lake Shore Drive apartment and we caught the last bit of sunlight from her building’s rooftop sundeck.
Sidenote: Chicago is all about a rooftop. They put bars on rooftops, pools on rooftops, barbecue grills on rooftops, sundecks on rooftops, restaurants on rooftops… they.love.a.rooftop. And I’m not mad about it. With views of Lake Michigan coastline, the greenery of Millennium Park, and city skyline, I see the appeal. This was our first Chicago rooftop, but it certainly was not our last…
We strolled over to Wrigleyville for a little bar hopping and started at a dive called Merkel’s for some catching up. Next, was Old Crow, a huge bar with a very, very happening rooftop. After that, Amy took us to Country Club, where FSU fans meet to watch games and celebrate all things Noles. The patrons are labeled Windy City Noles, how cute is that?! Our last bar of the evening was Trace, another dark watering hole that plays old music videos and has the coolest album artwork on the walls. (A highlight of my evening may or may not have been watching the music video for “You Can Me Al“) Per Amy’s recommendation, we ended the night at Cheesie’s, a pub grub stop offering any and every kind of grilled cheese you could ever imagine. It was the perfect food after a night of drinks.
The next day we hit the city’s best attractions. Beginning in Millennium Park, we snapped photos at Cloud Gate, the iconic reflective sculpture created by Anish Kapoor. It’s been a staple of the city since 2004 and as you can see, scores of visitors flock to it everyday to snap photos and take souvenir selfies. Apparently, it’s called Cloud Gate because 80% of its surface reflects the sky. I think it’s an amazing choice for this city because part of the piece is the iconic Chicago architecture it reflects.
With that stop checked off the list, we grabbed food from a nearby food truck and ate outside before venturing into the Art Institute of Chicago. The Gaugin exhibition was extensive, and I recognized several works by contemporary artists I also viewed at The Broad in Los Angeles, so that was very cool. Although it was small, they had a graphic design gallery, which showcased typography and branding elements from local agencies. Also, I have never seen Victor excited about anything in a museum but he just about lost his mind when he found Seurat’s “La Grande Jatte.” Per his request, I took his photo in front of it, a la Ferris Bueller’s Day Off.
After the museum, we walked more of the park and ultimately decided to grab a bite in Greek Town. Oh yah, in case you haven’t notice yet, the theme of this trip is food. All the food. And drinks. Many, many drinks. I had the best spanakopita I’ve ever tasted while sitting street side at the open-air cafe Artopolis. From there, we happy houred at the very happening, City Winery Riverwalk. We sat on the river bank and enjoyed the world’s most expensive Old Fashioned while ogling beautiful millennials docked on boats, and tour groups of kayaks floating by.
From there, we walked the Navy Pier, another tourist staple that could not be missed, and made it back to the hotel to recharge. That night I was not super pumped to go out so we made a quick appearance at the J. Parker (another rooftop!) for a cocktail. I only mention it because, 1, we were dumped underground by our clueless Uber driver while trying to get there, which was obviously terrifying and annoyingly nowhere near our destination. And 2, I had the best cocktail when we finally made it there! The Pacific Coast Highway – a gin drink, which I didn’t even know I liked gin, but it was delish and the silver lining of my evening. Also, I thought underground Chicago looked like Gotham City… and found out IT. IS.
The next day was Fourth of July. Yayyy, America! We did brunch at Brunch and made our way back to Wrigley to watch the Tampa Bay Rays play the Cubs. I was pumped for this game because although I make a concerted effort to not follow any sports of any kind, I genuinely like baseball and realized I kinda missed it. And what’s more American than watching the country’s favorite pastime at its most historic baseball stadium? Tampa Bay won and I sat next to a nice, old gentleman who fell asleep during the game. After, we hopped Wrigleyville bars again before taking the L back to Michigan Ave. Sadly, we didn’t catch any fireworks, (I KNOW. But, if you’re really heartbroken about it, here are some fun fireworks :)) but between baseball and team spirit and day drinking and music and beautiful Chicago, the day was one of my favorites on the trip.
The next morning I snuck out for a quick walk around Michigan Ave. before we made our way back to Millennium Park for the Taste of Chicago. Here is where we ate all the food. The annual food festival is famous for showcasing Chicago’s best eats and I purposely scheduled my trip to ensure my attendance. We spent the next three hours hopping from booth to booth to sample toasted ravioli (SHOUT OUT, ST. LOUIS!), Lou Malnati’s pizza (which, I’m still craving, btw), shrimp & grits, pierogis, green tea ice cream, and Chicago-styled hotdogs. Each booth offers “taste-sized” portions so you can try a few bites of several different dishes without barfing from gluttony.
I was also informed that Buckingham Fountain (see above) is the fountain from the Married with Children intro… something I literally never cared to know and yet, now I do. Thank you, Vic.
After eating all the food we could handle and getting a pretty gnarly sunburn on my shoulders, we decided it was time for a cocktail. We walked over to the Chicago Athletic Association Hotel and hit up the gorgeous ROOFTOP bar, Cindy’s, for panoramic views of the city and prime people-watching. It can get a little crowded with tourists snapping photos along the outdoor railing (I tried to take my photo as quickly and discreetly as possible), but we found a seat on patio and just took it all in. The ambience was welcoming and my cocktail was phenomenal. Repeat after me: Cocktail + sunshine + amazing view = vacation
That night, we set out for The Second City, Chicago’s famous comedy club, that has produced comedians like Chris Farley, Tina Fey, and Dan Akroyd. The show, Fantastic Super Great Nation Numero Uno, was phenomenal and hilarious and shed a comedic light on our current political climate (which these days, let’s be honest, is not hard to do!).
After the show, we Ubered to Wicker Park in search of the elusive bar The Violet Hour. I read about it before our trip and when Vic and Amy brought it up earlier in the week, I knew we had to go. The bar is hard to find because the facade is an ever-changing mural with a hidden door. Upon our arrival, a sharply dressed gentleman carded us, granted entrance, and led us through a dark corridor before we were left alone in front of a heavy, velvet curtain. I secretly wondered if we were being screened as we stood in a dimly lit hallway with nothing but a copy of the house rules to glare at on the wall. A few minutes later, the swanky gent returned (I guess we were approved) and led us through the dimly lit bar, past another set of velvet curtains, where two plush stools were provided at the gorgeous marble bartop. It was exciting but also felt like I was crashing the meeting of a secret society. The bar was not packed but there were enough patrons to prevent that ghost town feeling.
The Violet Hour boasts pre-prohibition libations so it did not surprise me when the bartender looked like an attractive albeit old timey apothecary. He was very welcoming and watching him make our cocktails proved entertaining. While this establishment has strict rules, like no phones and no cosmos, the people and atmosphere lacked the pretentiousness that can sometimes accompany bars like these. I’d like to tell you what I had, but having not been able to document it on my phone and maybe having a few at the comedy show, keeps my memory fuzzy. It had gin and fizz and it was pink and had a little herb shrub as a garnish. It was also insanely refreshing, and coupled with great conversation.
Having the slightest bit of room in our tummies, we decided it was time to eat again. (Remember, all the food.) Fortunately, retro vibe taco joint Big Star is directly across the street from The Violet Hour so we stumbled in and chowed down on queso fundido and pork belly tacos. My favorite was the Walking Taco, a bag of corn chips topped with the all the makings of a taco, right in the bag. Get it…?! Cause you can walk with it…! Is there anything better than post-drinks tacos at 1 a.m.? The answer is a resounding NO.
The next day we checked out of our hotel and walked to Lou Malnati’s for another date with destiny. I mean pizza. Pizza that tastes like destiny and history and everything that is good in this mixed up world. There are a few pizza places that boast the city’s best pizza but once I had Lou’s, I was pretty convinced the search could be called off. After, we picked up some souvenirs – Victor bought out Garrett’s Popcorn, and I found my go-to souvey, a coffee mug, at Intelligentsia. We drove through Wicker Park and Little Puerto Rico before heading back to Indy. It only made we wish we had more time. Next time, I’d like to start with Wicker Park and Logan Square because I saw so many cute bookstores and cafes.. and hipster-folk.
As far as first visits go, I think I hit the high points. I love the city and there is so much more I want to see/do/eat/drink/experience. I’m definitely not done here, and can’t wait to go back for more, so please feel free to send me your recommendations!
Chicago, I love you!