Chicago had “A Little Sumpin Sumpin” for me this weekend. I had not traveled to the city since pre-Covid, whereas before I was visiting this beloved city on a yearly basis. The media hype had led me to believe Chicago was out of control and chaotic and I would be out of my mind and irresponsible to travel to such a destination by myself. My heart could no longer take it and I had to take the risk and go see Her. Instead of taking the orange line from Midway airport I would be safe and take an Uber. I would forgo the $2.50 ‘L’ train fare for a safe $38 trip, in an Uber with a stranger, not knowing what his/her driving skills would be. Safer? Not Sure. I can report that my trip was 35 minutes instead of an hour and I arrived safe and sound at my destination; Warwick Allerton Hotel on Michigan Avenue.

I had not frequented this hotel and was delighted to find a cozy boutique hotel with friendly and accommodating staff. The hotel was built in 1923 and had completed 10 years of renovations in 1999. I was delighted to find that they kept true to the beginnings of the Warwick, as I was surrounded by the beautiful 20s décor. My eye caught the elevator dashboard lighting up as the locations of the various elevators were displayed. I felt a sense of euphoria thinking of others in this hotel being as lucky as myself and getting to have moments in this blustery beautiful city. My arrival was 8:30 a.m. so I had no expectation my room would be available but would leave my bags and start reacquainting myself with my missed love. I was pleasantly surprised to hear that my room was in fact ready. I dropped off my bags on the 9th floor and feeling the electricity of the city immersing in my bones, I quickly made my way back down and headed out the door to the nearest quaint café for breakfast.

I happened upon Sunny Side Up Café around the corner on Superior Street. I would have to pass on outdoor seating today — even though it is one of my favorite things about the city, dining and watching all the energy flow in and out of the streets — as the temps were chilly with a slight breeze but not brutal slap you in your face as it can be. The café was just as I had hoped, up the stairs to a cozy area with nooks and crannies filled with tables and chairs for two, four, or six patrons. I was greeted by a friendly waitress with a warm smile. My joy was exploding from the top of my blonde head as I sipped the first taste of delicious coffee looking over the cup with love at everything my eyes feasted on. My tummy was beginning to grumble and, although the menu wasn’t overwhelming, there were many choices. Everything sounded mouthwatering, but I would finally settle on ordering the Bacon Avocado Benedict. It was one of many great decisions I made that day!

After exploring the Art Institute, I headed to Giordano’s to sink my teeth into Chicago Style Deep Dish pizza. Always order “The Original”. The 40-minute wait is oh so worth it. But the highlight, highlight of my day would come in the evening at the James Nederlander Theatre. As my luck would have it, the Broadway tour of Tina: The Tina Turner Musical was kicking off its North American tour in Chicago. In my long black ruffled dress, burgundy boots, and evergreen fur cropped coat, I headed to the theatre on Randolph Street. The 1920s theatre was beautiful beyond words. The ornate décor paid homage to its original grandeur as my eyes drank it all in. I shimmied my way up to the bar and ordered the “Proud Mary”. A delicious cocktail infused with passion fruit syrup, rosemary syrup, vodka, and angostura bitters. My eyes were feasting, my mouth was dancing, and my ears were consumed by the chatter of anticipation and expectation. In a matter of time the chatter would turn into an uproar of hoots, hollers, and clapping. The show was more than I hoped for, with a cast that was phenomenal, which transported me back in time to one of the best days of my life when I saw Tina live in concert, with my mom, for her 50th birthday. The show elicited so many wonderful things from my soul: tears, laughter, joy, fear…it made me feel ALIVE. Tina Cast you were Simply the BEST!

As I headed back to my hotel the wind, slight rain, cold could not wash away my exuberance or steal the warm feeling in my heart. The next day was spent consuming wonderful knowledge at Let’s Just Write, An Uncommon Writer’s Conference located in The Tip Top Tap room, which as you can surmise was the tip top of the hotel. My time in this magnificent city was winding down but I had to do something to pay homage to my beloved Cubs. Harry Caray’s would do the trick.
I walked into the historic building on the corner that is overpowered by the high rises all around it, but it holds its own as the upkeep on the building is impeccable. As soon as I walk through the door the room is imbued with Chicago Cubs memorabilia. I have made reservations as you don’t stand a chance of getting into the “Best Steakhouse in Chicago” on a Saturday night without such planning. I am escorted to the restaurant on the left, away from the patrons that are surrounding the bar for a quick drink. The meal becomes an experience for me as my heart keeps reminding me how grateful I am to be here right now at this moment. Although Harry’s is known for steak, I am not much of a red flesh eater so I settle for the Whitefish Oreganato. A delectable seared fish swimming in toasted garlic and lemon snuggled in wilted baby spinach. As I observe all the lives intertwined in this space for a brief moment in time, it takes my breath away. I decide to enjoy the atmosphere for a bit longer, so I order an espresso martini to cap my meal off. As the espresso, Kahlua, and vanilla vodka dance on my tastebuds, I think to myself I may be the luckiest woman on the planet. My time is up, and I need to give up my seat for the next lucky person. I head out the doors and decide to walk back to the hotel as I know my time is winding down with Her.

I pass by the Red Head Piano bar and decide to peek in. The piano player in front is in full playing mode and the crowd is in full party mode. People are packed around the bar and standing shoulder to shoulder having the best time as Piano Man plays on figuratively and literally. When the song finishes, I pop back on to the street heading back to my hotel. I don’t want the night to end as I know this means my time with Her is nearly over. So I head to the M Avenue Lounge on the 2nd floor of the Warwick Allerton. As I sip “A Little Sumpin Sumpin,” I reflect on the last 40 hours and try to burn them in my brain so, when needed, I can flip through my rolodex of memories on those days that seem never ending dreadful and remember I always have Chicago waiting for me.

Written by: Kimberly Garber

 Kim Garber picture
Kimberly is passionate about life and loves to pursue all the world has to offer. She is an accountant and business teacher by day and loves to fulfill her creative outlet through writing. She is currently working on her first novel, Love Letter to Louie. Writing and running half marathons around the country are her therapy and she is excited to see where these pursuits will take her. She has been blessed with three beautiful children and is currently raising them with her husband in a small midwestern town.

For more ITKT travel stories about USA
For more ITKT travel stories about North America