On my first trip to Chicago, my boyfriend and I stayed in a seedy-looking motel a long bus ride from everything other than a White Castle. Chicago isn’t a cheap city to sleep in, and after previewing the cost for a hotel room for our second trip, we threw caution to the wind on our most recent trip and rented a place in Lakeview on AirBnb last weekend to be close to the theater at which his brother is performing his first solo show.
During our first visit, my boyfriend and I had done a lot of the touristy stuff. We did the architecture boat cruise, which should be a mandatory activity for all first-time visitors to the city. I developed an opinion on the best deep dish pizza (Peaquod’s) thanks to my boyfriend’s brother. We caught a show at Second City. We posed for an obligatory selfie under the Bean and stood on the glass platforms on the Willis Tower.
Last weekend, we visited the Shedd Aquarium, which was great, if a little spendy. We did some shopping on the Magnificent Mile, which I first got to know watching Oprah as a kid and hearing the show sponsorship messages as the credits rolled. I insisted on another stop at Peaqoud’s and DMK Burger Bar which we’d enjoyed during our first trip.
My favorite moments on this trip were the ones that weren’t overly touristy. While Second City is mobbed by out of towners, the Annoyance Theater is more of a comedy sleeper cell, located in a new space in Lakeview. It’s produced talents like Stephen Colbert and is more offbeat and local. It was great to watch my boyfriend’s brother’s first solo show and to catch a few ensemble productions.
Before leaving Boston, I had considered tossing in some workout clothes in case I felt the overwhelming urge to go for a run while we were on town. Our AirBnb was about a mile from the Lakefront, so I figured it may be nice to get some fresh air. I decided against it, which I immediately regretted upon arriving to the breathtaking skyline of Chicago. So after dinner one night I excused myself, walked over to a nearby Marshall’s and bought some workout clothes. (Hey, I needed them anyway.)
I got up early on Sunday to go for a jaunt by the water before we got ready to leave town. Not wanting to tire myself out before I got the water, I took advantage of Chicago’s bike sharing service and pedaled down to a station near the paths along the lake. Once I’d docked my bike, I started jogging.
The lake was still covered with fog, the sun trying to push its way through. Joggers, bikers, walkers, and serious groups of distance runners all cruised along the well-kept pathway. It was reminiscent of Boston’s Esplanade, but the path was set farther from the road, making it slightly more peaceful. Although it was too early for them to be open, small cafes were spread along the path for thirsty athletes and hungry tourists on a stroll. People lined up along the water to fish.
As I made my slow jog along the path, I rounded a gentle corner and saw the impressive Chicago skyline before me. It was still shrouded in fog, but the outline of the Willis tower and the Trump Tower were still visible. Somehow, Chicago has the height and density of New York City, but I don’t find it as imposing or overwhelming. Maybe it’s because the city goes for miles beyond, offering lakeside high-rises and small apartment buildings like the one I was staying in. Once I’d seen the skyline, I turned to head back. While it was not a good run from a pacing or distance perspective, it was the happiest I’d been after a run in weeks.
I love that, unlike Boston, most Chicago neighborhoods have the basics for urban living right outside your door, even if you’re 10 miles outside the downtown area. Lakeview had grocery stores, take-out joints, a variety of bars, wine shops, and bagel places within a 10 minute walk of our place. And, after an ill-advised urge to load Zillow on my phone, the real estate for sale was the same price as metro Boston, but each unit seemed move-in ready.
For our last meal before heading out of town, my boyfriend’s mother requested that we visit the Grand Duke’s Restaurant, a Lithuanian restaurant a few miles from Midway airport. She reveled as she eavesdropped on men at the bar speaking her native tongue. We all marveled at the sheer quantity of food that came with our order. It was amazing, and I’d consider dealing with the hell on earth that is Midway in order to have an excuse to stop in again.
Jeez, 800 words. That escalated quickly. All this is to say; I like Chicago and would consider living there were it not arctic cold there for half of the year.