My Kind Of Town . . . To Visit

That Toddling Town

It was half a lifetime ago when I made my first visit to Chicago. I was 18 years old, a college freshman on a road trip to DC with a group of friends. We crashed for a night on the outskirts of America’s third largest city, and I marveled at the unfamiliar, slightly gritty, architecture and the way the buildings all seemed to crowd together. On our way out, we drove past a billboard on 1-90 which towered so steeply alongside the highway that it almost seemed to compete with the Chicago skyline. In bold black letters, the billboard read: “Who’s the father? 1-800-DNA-TEST” My travel companions and I thought this was a hoot, and as we continued driving, I couldn’t help but wonder: “What kind of town is this?”

The Jewel of the Midwest

I wouldn’t return to Chicago for another five years. My good friend Ben, whom I’d met while studying in Albuquerque, had agreed to meet me in the city for a few days. I traveled via Amtrak; it would be my first long-distance train ride. The views from the train were spectacular, especially when I spotted a convocation of bald eagles perched along a watershed somewhere in Wisconsin.

Arriving at Chicago’s Union Station, I stepped off the train platform and gasped at the sight of a late afternoon orange glow settling over a city that seemed to bleed steel and concrete. And, striking as it was, this city was cold. Extremely cold. God-doesn’t-love-you-anymore cold. Having recently developed an eating disorder, I now had only enough body fat to keep me warm in Chicago in — oh, say in the month of August. But this was February, and as I would soon find out, I was screwed, even underneath several layers of cotton and wool.

We’d booked beds in a hostel near Loyola University. It was cheap and convenient to the L. The dorm rooms were nothing special, but the hostel offered a common area with brightly painted walls and a shared kitchen where we could cook if we wanted.

“Have you lost weight?” Ben asked only minutes after our first reunion in well over a year.

I wasn’t ready to deal with my — ahem — issues yet, so I quickly changed the subject. Over the course of the next five days, we explored the city together: the Magnificent Mile, a vegan restaurant in Wicker Park, the Art Institute of Chicago, the Museum of Science and Industry, The Green Mill Cocktail Lounge, and the Navy Pier. Crabby throughout most of our trip, I don’t know how Ben managed to put up with me; I could barely stand myself at the time. The only respite was when, a few nights into our trip, we smuggled a hefty supply of Heinekens into the hostel and spent the evening guzzling them. For one evening only, I set aside my obsession with calorie counting and managed to have some semblance of fun. We befriended a young Scottish fellow in his late twenties: a schoolteacher named Duncan who was traveling the globe on Sabbatical. He had a charming accent and a great sense of humor and he kept us in stitches with his stories about his worldly adventures thus far. Duncan turned out to be about the best thing to come out of that trip. Ben and I each kept in contact with him for several years after that, and he even popped in to visit me in Minneapolis a month later.

The Windy City

At age 30, I found myself in Chicago yet again. This time it was late September: the weather was crisp but not bitterly cold the way it had been during my last visit. I was in town to meet up with a friend, Viviane, a charming Belgian-American gal whom I’d come to know during a two-year stint in Boston. This would be Viviane’s first time in Chicago. The two of us had booked a room at the Renaissance near O’Hare Airport.

Having shed my eating disorder by this point, I was able to enjoy the Windy City in a way I hadn’t been able to with Ben seven years prior. Viviane and I revisited a few of the places Ben and I had gone my last time in town, as well as some new ones, such as Buckingham Fountain in Lincoln Park, Smith Museum of Glass, and Chicago-style pizza at Geno’s East. Although in my eating-disordered days I’d been known to shun both pizza and people who enjoyed it (a sad fact my dear friend Katy will never, ever let me forget), it was me who steered Viviane away from ordering a salad at Geno’s East. In the end, I’m quite sure she’d agree that ordering pizza was the right decision. The deep-dish pizza for which Chicago is so well-known was smothered in four types of cheese that melted in your mouth and settled in your stomach in a mound of warm, doughy goodness.

On the last night of my trip, we met up with one of my high school friends, Erica, who had moved to the city several years prior. The three of us enjoyed drinks and appetizers at the Purple Pig for Viviane’s 30th birthday. This was a rather serendipitous moment, considering that Viviane’s favorite color was purple and that she — to this day — nurses an unhealthy obsession for the queen of all swines, Miss Piggy herself. Good food, good friends, and many laughs made for an excellent trip. I came home feeling happy and relaxed.

The Second City

Flash forward five years. I’m married and living in Philadelphia. My parents-in-law have settled in a sleepy Wisconsin town two hours outside of Chicago, and it’s recently come to my husband’s and my attention that we may need to check in on them every so often as they get on in years. The thought occurs to both of us: Why not consider living in Chicago? It’s a world-class city that would be fun to explore, and close enough to hop in a car and see our families should the need arise. Our trip to Chicago in February is thus a fun getaway but also a way for us to metaphorically dip our toes in the water that flows through the heart of the Second City.

Traveling with my husband Jeff, a self-confessed foodie, one thing was for sure: we were going to eat well or not eat at all. And of course we had to eat. (Hey, I shed that nasty ED for a reason: I love food.) The most tantalizing meal we shared was brunch at Chicago Q, a high-end BBQ joint in the Gold Coast Historic District. I overindulged and felt nauseous for the remainder of the day, but oh, what a spread!

Brunch at the Chicago Q
Brunch at the Chicago Q

Perhaps the most memorable moment during our trip was the brisk — on second thought, make that freaking frigid — walk around Wrigleyville in search of the Cubby Bear Sports Bar, where many years ago Jeff had eaten his first Chicago hot dog. Sadly, when we arrived the place still hadn’t opened its doors for business — it was still too early in the day. So we circled Wrigley Field, chatting about how great it would be to see a baseball game if we did wind up moving there.

“Let me take a picture of you in front of the marquee,” I suggested. So Jeff posed in front of the infamous red and white Wrigley Field sign as I removed my mittens and snapped a series of pictures on my phone. I captured one good shot and then promptly realized that my hand was stinging and bright pink in the early stages of frostbite. All of this had transpired within less than two minutes.

Was it worth the frostnip? I like to think so.
Was it worth the frostnip? I like to think so.

“We need to get inside pronto,” I said, holding my hand inside my jacket and pressed tightly against my chest for warmth. “I don’t care where we go.”

Snow started falling lightly. It was so picturesque that, half a block later, I removed my injured hand from my chest in order to capture this scene. I couldn’t resist.
Diner in Wrigleyville

And still a moment later, this one . . . yes, I’m an idiot sometimes.

Poor robot.
Poor robot.

We made it to a bagel shop at the end of the block, where we ordered hot beverages and warmed up. My hand was pink for the rest of the day but there was no lasting damage. Plus, I had three good photos to show for it. I think it was then when I realized that Chicago would stay forever in my mind a travel destination and not a place to settle down permanently. [Sigh.]

Thanks for the memories, Chicago, but I’ve met my quota for bitterly cold days in one lifetime.

“Chicago, Chicago
That toddlin’ town
Chicago, Chicago
I’ll show you around
I love it
Bet your bottom dollar you’ll lose the blues
In Chicago, Chicago . . .”

-Music written by Fred Fisher in 1922 and popularized by Frank Sinatra in 1964


8 responses to “My Kind Of Town . . . To Visit”

  1. Ha, ha, yes I remember that day. We all have them though:). Would love it if you moved to the windy city:). Love you G!

    1. Hey goofball, did you read to the end? We ain’t movin’. It’s okay; it was a long-ass blog post. I probably wouldn’t have read the whole thing either. 😉 Love you!

  2. So happy you have no more disorder. Congrats on the wedding lol. Glad you had the deep dish. Did you guys get to have authentic hot dogs wrapped in paper with fries? There’s also a place called Ed Debevics you would have loved! 🙂

    1. Whew–me too. We didn’t have hot dogs but next time for sure! Thanks for the recommendation. I’ll check out that link you mentioned.

  3. Glad you’re deciding to stay local (at least for now.) My hubby reminds me every time I bring up wanting to visit the Windy City how freaking cold it is! He lived there for 3 yrs. before we started dating. I soooo enjoyed reading all your anecdotal stories also about your previous trips before this last one, Gina! Let’s just say, I’m ready to celebrate that beginning to Spring later this week. 😉

    1. I didn’t realize Brian had spent some time in Chicago! Yes, it’s insanely cold there. Lovely, of course, but difficult to endure. A Mid- Atlantic winter is about as much as I can handle for now. Happy almost-spring!

      1. …..AND! Can you believe this Friday, the first day of Spring we are having!? I’ve never seen such weather-related insanity here 😦 Hope you, hubby, BG and kitty are inside and warm, Gina! 🙂

      2. I’m starting to suspect the next Ice Age is near. What a way to ring in the spring season. Hope you and your family are somewhere safe and cozy!

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