Two Days in Chicago: The Loop, The Lake, and Boystown

I gave myself two full days in Chicago before the Empire Builder pulled out, and I used most of every hour. Not in that frantic way where you’re racing between attractions with a checklist, photographing things to prove you saw them. More like wandering with intent — letting the city reveal itself block by block, meal by meal, asking nothing in return except your full attention.

Chicago is not a city that has to work very hard to get your full attention.

The Loop on Foot

First morning, walked into the Loop and just looked up. That’s the move. Chicago’s architecture does something to you when you encounter it at street level — the buildings aren’t just tall, they’re theatrical. They lean into the sky with a confidence that borders on aggressive, each one competing with its neighbors for your eyes. The Rookery, the Wrigley Building, the Monadnock, the Marquette — this is where American architecture decided what it was going to be, and the city still carries that weight proudly.

The Chicago Riverwalk is the best free show in town. Glass and steel and limestone reflecting off the water, bridges lifting for tour boats, the whole thing managing to feel both enormous and somehow intimate at once. I walked the length of it twice. Grabbed coffee from a place with outdoor seating and watched the river move for twenty minutes without checking my phone. That felt like a small victory.

Spent part of the morning at the Art Institute, which I’ve been to before but will apparently keep returning to forever. Stood in front of Hopper’s Nighthawks for a while. The painting is smaller than you expect from the reproductions, which somehow makes it more affecting — all that urban loneliness compressed into a window-sized frame. Felt appropriate that I was looking at it on day two of a five-week solo trip across America, about to spend a lot of time eating alone in diners. If I had to say, I think Hopper understood something about the specific solitude of American cities that nobody’s quite captured the same way since.

Millennium Park after that. The Bean. I know it’s the most photographed object in Chicago and I photographed it anyway, because you have to. It distorts the skyline into fun-house curves and reflects your own face back at you from sixteen different angles, and there’s something genuinely delightful about that, no matter how many Instagram posts you’ve seen from the same spot. The crowd around it was enormous and cheerful and speaking about nine different languages. A guy was playing saxophone nearby. A kid was crying about something. Standard Millennium Park afternoon.

Then the lakefront, which stopped me cold. Lake Michigan doesn’t look like a lake. It looks like an ocean that wandered inland and decided to stay. The water stretches out to a horizon so far away you can see the curvature of the earth in it — deep blue fading to pale silver at the edges — and the scale of it recalibrates your whole sense of where you are. You’re in the middle of a continent. A thousand miles from salt water. And yet here’s this inland sea, lapping at the concrete like it’s always been here and always will be. Which, you know. It has. It will.

I sat on the rocks at the edge of the lake for a while and just looked at it. Didn’t need to do anything else with that moment. Just needed to be in it.

Boystown After Dark

You can’t plan a queer road trip through America and skip Boystown. That would be like going to New Orleans and not eating anything. Boystown, or Northalsted as it’s been more inclusively renamed in recent years, is one of the country’s oldest and most established gay neighborhoods. It occupies a stretch of North Halsted Street on the North Side, and the rainbow pylons are just the most visible signal of something that goes a lot deeper than public art installations.

Took the Red Line up on the first evening. Got off at Belmont, walked south. In summer the whole thing spills outward — bars and restaurants with their doors and windows thrown open, patrons taking up the sidewalk in chairs that technically belong to a different establishment. It’s somewhere between a block party and a living room. People are out in every sense of the word. Couples holding hands without performing it, groups laughing too loud about something, drag queens in full regalia moving with the confident efficiency of people who have somewhere to be and a show to get there for.

It’s the kind of place where being queer isn’t a statement. It’s just the baseline. The air pressure is different. You can breathe slightly differently here than you can in most places.

I had a drink at a bar that had been open since the ‘80s — the kind of place that doesn’t advertise its history but you can feel it in the walls, the worn bar rail, the way the bartender moves like someone who’s been doing exactly this for a long time and couldn’t imagine doing anything else. This neighborhood has been through it. The AIDS crisis, the political battles, the gentrification that’s still in progress, the ongoing conversation about who gets to feel welcome and who gets quietly priced out. The bars that survived all of that carry the weight of it. You can feel it if you’re paying attention.

Not performed resilience. Earned resilience. Different thing entirely.

Got a late dinner at a diner on Broadway. Sat at the counter, talked to nobody, ate well. The kind of meal that’s unremarkable while you’re eating it and then you remember fondly six months later.

The Quieter Day

Day two in Chicago was slower. Slept in, which I never do at home but apparently do immediately on vacation. Wandered the neighborhood around the Ohio House, took photos of things that caught my eye — a mural on a loading dock, a neon sign in a window, the way the afternoon light hit the back of a particular building. Not every day of a trip needs to be an event. Some days are just about being in a place, letting it absorb you, preparing your nervous system for what comes next.

What came next was the Empire Builder. Amtrak’s flagship long-distance route from Chicago to Seattle — forty-six hours on a train, crossing the full northern tier of the country. Wisconsin, Minnesota, North Dakota, Montana, Idaho, Washington. States I’d barely set foot in, landscapes I’d only seen in photographs that didn’t do them justice. I knew that because everyone who’d done this train said the same thing: the photos don’t do it justice. I was going to find out tomorrow.

That night I packed the train bag with the particular care of someone who knows they won’t have easy access to their luggage for two days. Book. Charger, backup charger. Snacks — more than I thought I’d need, based on nothing specific but instinct. Camera. Change of clothes. A tiny bottle of good whiskey, because some traditions deserve to start somewhere.

Chicago had been generous. Generous with its food, its architecture, its lakefront, its queer history. It gave me exactly the launch pad this trip needed: three days to remember why I love cities, before five weeks of watching the country change outside a train window.

Tomorrow I’d trade the vertical city for the horizontal country. The skyline for the prairie. The El for the rails.

I could hardly wait.