Wanderlost in Chicago

Frontier Airlines didn’t post the gate until ten minutes before boarding. Ten. Minutes. 

My boarding pass said Terminal A, but of course, the flight was leaving from Terminal D — an entire airport trek away—which feels like a cruel joke when you’re carrying a heavy backpack.

By the time I reached it, I was sweaty, out of breath, and regretting every last item I’d shoved into my backpack.

At the gate, the energy was that special brand of airport chaos — families juggling snacks, couples bickering about carry-ons, people crowding the boarding area waiting on their boarding group to be called so they can to the front of the line (drives me crazy). The doors were supposed to close at 12:10, yet it was 12:35 and people were still boarding.

The flight attendants made the classic announcement: “Every seat is filled — all 186 of them.” But somehow, magically, I ended up with an empty middle seat. For me, that’s the ultimate good-travel omen — the universe’s way of whispering, You’re going to have an amazing trip.

Still, I couldn’t shake an odd feeling as the plane taxied. Something about it felt a little… wobbly. Like teaching your kid to drive and feeling those too-quick bursts on the gas pedal. I tried not to overthink it, but my brain — ever the dramatist — started doing the math: “Frontier is cheaper. Why? Less experience? Older planes? Discounted physics? Are we all going to die?”

When the wheels finally lifted and we got in the air, I quietly laughed at myself. Same anxious flyer, same imaginary doomsday scenarios. No matter how much I fly, that never changes.

When the wheels finally lifted, and we got in the air, I quietly laughed at myself. Same anxious flyer, same imaginary doomsday scenarios. No matter how much I fly, that never changes.But somewhere between Houston and Chicago, I felt something unexpected — relief. There’s a quiet gift in being unreachable. If something terrible were happening back home, did I really want to know mid-flight? Probably not. I realized in that moment that there’s a certain kind of peace in forced disconnection. Maybe ignorance can sometimes be a soft, temporary kind of grace.

Also, the seats don’t recline.
 

And I forgot my airplane pillow. Again.

I landed in Chicago mid-afternoon, found my way to Club Quarters — a boutique hotel just blocks from the Sears Tower — and yes, I said Sears Tower—locals, I’d learn quickly, refuse to call it the Willis Tower, and I respect their rebellion. My room was small but clean, quiet, and efficient. Exactly what I need when I plan to spend as little time there as possible.

By 4:30 p.m., I was checked in, freshened up a bit, put on my cutest fall coat, and was out the door again, chasing the city before the sun went down. I hit the streets in search of food and adventure (and water, since Frontier doesn’t believe in free drinks). Hunger and curiosity led me toward the tower. I passed sleek glass buildings, watched reflections across their surfaces, and marveled at how alive the city felt.

Inside the tower’s lobby, I found a small Mexican place tucked into a corner — small but warm. I ordered a mushroom quesadilla and a margarita, because honestly, what better way to say vacation mode: activated? The food was great — melty cheese, soft tortilla, just the right hit of salt on the rim of my glass. I left full, revived, and ready for the sky.

Tickets to the SkyDeck were about $50 — a bit of a splurge — but I was already there and couldn’t resist the promise of the sunset view. Ticket in hand, I joined the line for the elevator, which felt more like a spaceship launch. The elevator was an experience all its own: enclosed 360-degree screens projected the Chicago skyline as we ascended—pressure shifting, hearts pounding, everyone pretending not to be totally impressed, as we raced up to the 103 floor.

When the doors opened, the room buzzed with that mix of awe and claustrophobia that only tourists can generate. It was hot, crowded, loud. But then I stepped up to the glass windows and looked out…

Chicago shimmered. The sky blushed pink and orange, the lake caught fire in reflection, and for a moment the whole city seemed dusted in rose gold. It was as if Chicago were flirting with me, saying, I know what draws you in. Welcome.

The next morning, I followed that feeling into the day.

The only thing I’d preplanned before landing in Chicago was a river cruise. I had asked myself, What’s the one thing I can’t leave without seeing? — and for reasons I couldn’t fully explain, the Chicago River called to me the loudest. Maybe it was the way it cuts through the city like a heartbeat, carrying history and stories through it.

I boarded The First Lady, a large river cruise vessel with — as it turned out — an all-female crew. Somehow, that felt important. There was an instant sense of strength about it — women confidently steering this massive boat through the city, doing something that for so long had been seen as a man’s domain. It felt like progress. Like power.

It made me quietly proud — not because I knew them, but because I saw myself in them. Here I was, a woman learning to navigate her own world, to trust my direction, and here they were, literally navigating me through part of my journey. It felt symbolic — a small, beautiful sign that I was exactly where I was meant to be.

The guide, a red-haired young woman, carried that brave, slightly nervous energy I recognize in myself when I’m trying to appear more confident than I feel. Her voice — steady yet soft — drifted easily over the water as she told stories of the city: its rebirth after the Great Fire, its architectural ambition, its grit. I found myself rooting for her as much as for the skyline she described.

The river shimmered turquoise beneath a 49-degree sun, and something inside me loosened. I leaned back, tilted my face toward the warmth of the sun, and took a long, deep breath. As the wind whipped through my hair, I felt something I hadn’t felt in a long time — complete ease. The kind of peace that sneaks up on you when you stop striving for it.

As the boat drifted beneath bridges and between glass towers, I realized how happy and free I felt — and began to wonder why. I think it was because, here, I was invisible. No one cared who I was, where I came from, or what I did for a living. Everyone was minding their own business, moving quickly, not wondering about me at all. There was no judgment. No expectation.

And maybe, just maybe, that’s what self-acceptance really looks like — the quiet moment when the noise of the world fades, and you connect with who you are when no one’s watching.

After the cruise, I wasn’t ready to stop exploring. My brain was buzzing with history, my heart was eager for more, and my feet — miraculously — still willing. So I did something unexpected. I bought a ticket for one of those big red double-decker bus tours. The ones I’d always avoided for fear of looking like (gasp) a tourist.

I climbed to the open top deck, sat in a row near the middle of the bus, and pressed play on the audio guide. For two hours, I let the city roll by like a movie.

It was… incredible.

I learned more in those two hours than I could’ve in days of wandering on foot. The breeze felt like a living thing, wrapping around me, playing with my hair. Every time we passed under a low bridge, I ducked instinctively, laughing to myself at how close it felt — Every bridge, every traffic light felt like an action scene waiting to happen — the kind where Spider-Man might leap onto the bus mid-battle while we all cheer. (hey, it could happen!)

For once, I didn’t care if I looked like a cheesy tourist. Maybe I am the cheesiest of cheesy tourists — and that’s okay. Cheese is quite delicious, after all.

As we circled the city, the audio guide told stories that felt cinematic — Al Capone’s Chicago, JFK learning about the Cuban Missile Crisis at the Blackstone Hotel, the dreams of the 1893 World’s Fair, Obama’s victory speech echoing through Grant Park. I imagined each one, painting mental scenes, wondering what it would have felt like to stand there, to be part of history as it unfolded. 

Chicago, I realized, is a city built on reinvention. It burns, rebuilds, and keeps rising — unapologetically bold. Maybe that’s why I felt so connected to it. I know a thing or two about starting over, too.

I got off the bus right in front of NBC Studios and decided to do what I love best — wander. No maps, no plan, just me and the city. I wandered aimlessly, my only goal being to learn — to see what the city might teach me if I let it.

Eventually, of course, nature called. (Finding a public bathroom downtown? A true urban quest.) But even that became part of the adventure — one more reminder that travel is never just about the postcard moments. 

I took photos of whatever caught my eye: a neat-looking street sign, the reflection of clouds across a glass tower, a man driving a motorcycle with his dog dressed in full vintage motorcycle gear and goggles (!). I watched people rush by, each one a little story in motion. Street performers played smooth, soulful jazz that wrapped itself around the buildings, and danced through the streets.

I tucked myself against a building so I wouldn’t block the flow of fast-paced Chicagoans, content to simply stand still and listen — to let the music, the noise, and the rhythm of the city wash over me.

A few blocks later, I passed a small crowd gathered near Trump Tower around a religious group preaching loudly on a corner — full of conviction and fire. I didn’t agree with their message, but I couldn’t help admiring their boldness, their unshakable passion for what they believed. Good for them, I thought, and after a few minutes, kept moving.

Eventually, my wandering led me to the shops — those retail wonderlands that only exist in cities like this. Chicago’s fall and winter fashion felt like another world compared to home: cozy sweaters, dramatic coats, boots that made me want to stomp through imaginary piles of leaves. And the stores themselves were massive — Macy’s alone was seven stories of temptation!

I could’ve spent the whole day shopping, honestly. But I wasn’t there to add more “stuff” to my life — plus, my bargain Frontier flight only allowed a tiny carry-on. Personal growth through luggage restrictions. Who knew?

There was something beautifully ordinary and yet quietly thrilling about that afternoon — just me, the city, and the permission to move entirely at my own pace.

By late afternoon, I realized I’d been running on caffeine and vibes — a Pumpkin Spice Latte (I know, so basic, but perfect). Once I realized how hungry I was, I headed back to the hotel, freshened up, chugged two big bottles of water, and went straight downstairs to the adjacent British pub — the Elephant & Castle. Having ended my night there the evening before, it felt almost familiar, like the city was quietly welcoming me back.

The pub was exactly what you’d hope for: cozy, a little dim, and cheerfully predictable in its British charm. It wasn’t trying to be too trendy or modern — just comfortable. I slid into a corner table and ordered a cup of French onion soup to warm me up and hold me over while I decided what to do next, and where the night might take me for dinner.

By the time I finished my soup, the tired parts of me — my feet, my back, and maybe even a little part of my motivation — were all begging me to call it a night. It was tempting, after such a full day. But alas, I wasn’t in Chicago to rest. So I gave myself a tiny pep talk: Get moving and have some fun, dammit.

Then it hit me — out of nowhere — like a lightbulb flickering on above my head: I need a laugh. A comedy club. Yes, that’s exactly what I needed. Before I could overthink it (or talk myself out of it), I looked up the address to Second City, the only comedy club I’d ever really heard of in Chicago. Within minutes, I was in a taxi, heading toward what turned out to be one of my favorite neighborhoods of the entire trip — Old Town.

It’s only about a mile from downtown, but it feels worlds away. As we drove, I noticed the shift immediately. The air felt calmer, the streets cleaner, and the neighborhood somehow softer — like the city had taken a deep breath. The rows of beautiful brick townhomes reminded me a bit of New York, yet quieter, homier.

I found myself gazing through the softly lit windows, catching fleeting glimpses of the lives inside. What must it be like to live here? To come home to a place like this every night? What’s their secret to such a good life?

At almost forty, I’ve learned that most things look happier from the outside than they really are — but in that moment, it was hard to believe anyone could live somewhere so picturesque and feel anything but joy.

The cab stopped in front of Second City, but instead of heading straight to the box office, the pull of wandering got me again. I let my feet lead me through Old Town’s charming streets — a place that somehow felt both peaceful and alive. Laughter drifted from open doorways. College kids crowded around bar patios. Families lingered over dinner. And surprisingly, there were a lot of people like me — alone, but not lonely. Just content.

This neighborhood is magic, I thought. I want to live here. (A thought, I should note, that crosses my mind on almost every trip.)

Eventually, the smell of something heavenly stopped me in my tracks. A place called Professor Pizza beckoned from the corner, its warm light and the scent of fresh Chicago pizza practically calling my name. I slipped inside, ordered an Aperol Spritz (which was fantastic), and opened the menu — or at least, I pretended to. Because instead of choosing what to eat, I found myself scrolling through local real estate listings. You know… purely for educational purposes.

I lost track of time and realized I didn’t have enough of it left to order food if I wanted to make a comedy show. I had decided against Second City when I discovered it was mostly sketch comedy — which, if I’m being honest, has never really been my thing. Instead, I found tickets for a 9:00 p.m. show at The Comedy Bar, so I quickly paid my tab and said goodbye to Old Town.

As it turned out, the venue was near the Magnificent Mile. So yes, I’d technically “wasted” money on a taxi to a show I didn’t end up attending — but that’s the beauty of wandering, isn’t it? You never really know where you’ll end up, but somehow it still feels like where you’re supposed to be. I got to see two neighborhoods I might’ve otherwise missed. How lucky am I?

The Comedy Bar was tucked inside a small building above a restaurant — intimate, unpretentious, and exactly what I hadn’t realized I was craving. I ended up getting to the venue pretty early (what can I say — time math and I have never worked out), so I went to the bar downstairs and found an empty seat at the very end of the counter. 

Within minutes, the last two open seats beside me were filled — one by a pretty twenty-something woman, and the other by a man in his late forties or early fifties who looked like he was firmly on the prowl.

It was clear they weren’t together, judging by their small talk — polite, slightly awkward, mostly led by him. He was an anesthesiologist; she, as it turned out, was a nurse trying to transition into aesthetic nursing. Something I happen to know a thing or two about after many years in the industry.

He was trying hard. And I recognized the scene immediately — I’ve lived it. That moment when someone’s hitting on you with unrelenting persistence, and you’re too nice to tell them to back off. You smile, you nod, you pray they’ll take the hint — and they never do.

So I decided to throw her a life raft. She could take it or leave it. I was also self-aware enough to consider maybe my instinct came from my own bias — that maybe I just didn’t like seeing older men pursue much younger women because it triggered something in me. After all, maybe she was into it. Who was I to intervene? 

Still, I leaned in politely and said something along the lines of, “Sorry to interrupt, but I couldn’t help overhearing you mention aesthetic nursing…” — and that was all it took. The relief on her face was instant. She turned her body toward me, back to the man, fully engaged, and never looked back at him.

He, meanwhile, shot me dagger eyes for the next twenty minutes. (Oops.)

She was lovely — sweet, curious, easy to talk to. I loved listening to her describe her plans, her dreams, the way she still believed in love and possibility. She hadn’t yet been jaded by disappointment, not in the way life eventually jades us all. I felt a tenderness toward her — for who she was now, and maybe a little for who I used to be.

What a beautiful time in a woman’s life, I thought — when the world still feels wide open, and you truly believe that all the good things waiting for you are just a matter of time. I hoped she’d hold on to that belief for as long as she could. Quietly, I sent a little wish into the universe for her — just one woman to another — that life would be kind, generous, and everything she dreamed it could be.

When she mentioned that her boyfriend was sleeping at the hotel and that she was going to the same comedy show I was heading to, I almost invited her to sit with me. But I didn’t.

I was here to solo travel — to prove to myself that I could do things alone. Sitting by myself in a comedy show scared me, which is exactly why I needed to do it. There’s something about being the person with the empty seat beside them that feels… exposed. My worst fear was that the comedian would call me out — the lone traveler, the awkward punchline, the circus freak.

But I’m learning that’s the thing about growth: it usually hides behind discomfort. And I was determined to meet it head-on, even if it meant laughing alone in the dark.

The hostess tried to seat me in the front row — right up against the stage. I decided I wasn’t that brave yet and asked for a table a little farther back. Still, in a room that small, there was no hiding. I was well within the comedian’s eyeline — close enough to feel seen, but far enough to breathe.

A man ended up sitting at the table next to me, also traveling solo. We exchanged a few minutes of small talk — just the kind of polite conversation that feels natural when two strangers find themselves sitting in close proximity in a comedy club. And then, somehow, we discovered that he lived in the same suburb of Houston where I work. What are the odds? A small world moment, even hundreds of miles from home.

I didn’t engage much beyond that. It’s unfortunate, really, that as a woman you have to calculate those things — the line between friendly and too friendly — worrying your kindness might be mistaken for interest. I didn’t want to give the wrong impression; I just wanted to enjoy the show, alone and safe.

When the lights dimmed, the chatter settled into a low hum, and the host bounded onto the stage with the kind of energy that only comes from caffeine or chaos. The crowd roared with applause, and I found myself clapping too, already smiling.

One by one, the comedians took the stage — each bringing their own brand of comedy, heartbreak, and hilarity. Within minutes, I was laughing out loud — not the polite kind of laugh you give to fill silence, but the full-body kind that sneaks up on you, the one that leaves your cheeks aching and your soul lighter.

Somewhere between the bits about dating apps and airport security, I realized something small but beautiful: no one cared that I was alone. No one pointed it out. No one made me the punchline. I was just another person in the dark, laughing with everyone else.

By the end of the show, my sides hurt, and I couldn’t stop grinning. Laughter really does something to you — it unsticks the things that worry glues down.

After the show ended, I ordered an Uber back to the hotel. It was late, and since it was my first time in Chicago — alone, no less — I decided to skip the late-night stroll and play it safe.

I wandered back into the Elephant & Castle pub one last time and ordered a sandwich to go, plus a nightcap while I waited. The place was buzzing — packed with people in Halloween costumes, most of them college-aged, loud, and full of that kind of unshakable confidence that only comes with being twenty.

Nothing will make you realize your own age quite like being surrounded by college students on Halloween weekend. Their energy made me both smile and cringe.

The service that night was… not great. I ended up waiting far longer than I wanted to, growing increasingly hungry and mildly irritated. But as it turns out, even irritation can be interesting when you’re people-watching in a new city. The laughter, the costumes, the easy way everyone seemed to belong — it all felt like a reminder that life is still happening everywhere, even when you’re tired and ready for bed.

By the time I crawled into bed that night, I was full — of food, laughter, and that delicious kind of exhaustion that only comes after a day well lived. I felt a little sad knowing I’d be saying goodbye to Chicago in the morning, but mostly grateful for everything the city had given me in such a short time.

The next morning came too quickly. I showered, packed, and found myself in an Uber heading back to Midway Airport. My driver wasn’t much of a talker — a rare and welcome blessing. Normally, I love a good chat with an Uber driver (being somewhat of a chatterbox myself), but that morning I was content to sit quietly, forehead against the window, watching the skyline fade into the distance.

At the end of every trip, my daughter and I play a little game we call High, Low. The rules are simple: we each share the high point and the low point of the trip. It’s our way of wrapping things up — reflecting, laughing, and remembering together.

For this trip, my high was the double-decker bus tour (who knew I’d been missing out on such FUN just because I didn’t want to look like a tourist?). And my low? Definitely Frontier’s strict carry-on rules. What a nuisance. I ended up having to pay for my bag on the way home — more than I’d paid for the flight. Bah humbug.

As the plane rose into the air, I watched the city fade below and felt that sweet, quiet ache that comes at the end of every good adventure.

I didn’t go to Chicago in search of anything profound, and it didn’t hand me some grand

revelation — it offered something softer. Space. Privacy. The gift of being invisible in a city too busy to notice me. Without eyes on me, I stopped curating who I was. I said what I wanted. I wandered where I pleased. I listened to the small voice I usually drown out, trying to please everyone else. And in that unguarded space, I found something that felt a lot like peace.

I also learned that Chicago is a city of reinvention, and I saw my own story in its skyline — the burning, rebuilding, rising again. It reminded me that starting over isn’t a single act, but an ongoing rhythm of learning. That I am no different. That I, too, can rebuild.