Arriving in Chicago: The Starting Line

I’d been planning this for months. Spreadsheets, saved maps, a camera bag packed and repacked three times in the same week. And then I’m in the window seat, the plane banking over Lake Michigan, and the skyline materializes out of the summer haze like a thing I’d only imagined until now. It’s actually happening. The Eat Gay Love trip is real.

The concept sounds simple when you say it out loud: a solo cross-country trip through queer America, eating my way from Chicago to the Pacific Northwest by train and whatever else gets me there. Five weeks. No boss to check in with. No recycling schedule. Just me and a country I’ve lived in my whole life and don’t actually know as well as I think I do.

The execution part is considerably more chaotic, which is, if I’m being honest, most of the appeal.

Leaving Silver Spring

I left home that morning and it already felt like a week ago by the time I landed. The cab to DCA, the security line, the nine-dollar terminal coffee I bought anyway because it was there and I was anxious. Maryland in July is a steam bath. Stepping outside at the airport is like walking into a warm, wet towel someone left on a radiator. I’d been warned that Chicago would be similar. But different-hot is better than home-hot, so I wasn’t worried about it.

There’s something that happens the moment the wheels leave the ground. Some mental switch. You’re not the person who checks email before 8 AM anymore. Not the person who knows where the nearest pharmacy is. You’re just someone in motion — temporarily freed from the gravity of your own particular life. I felt it come on as the Potomac disappeared below the clouds. That unlocking. It doesn’t happen on trains the same way, or on drives. Something specifically about the altitude does it.

Two hours. Chicago.

I’ve been here before. Chicago isn’t new to me. But arriving somewhere with the specific intention of paying attention to it — writing about it, documenting it, being a traveler here rather than just passing through — changes how it registers. Coming in on the Kennedy, the skyline builds gradually. The Sears Tower first. Yes I know, Willis, but I’m from the generation that named it and I’m keeping it. Then the Hancock. Then the whole dense stack of it against the summer evening sky.

It doesn’t matter how many times you’ve seen it. It still does something to you.

The cab driver was from Senegal originally, had been in Chicago eleven years. Told me the Cubs were having a rough summer and the White Sox were having a rougher one, which I gathered was meant to be comforting. I didn’t have the heart to tell him I don’t follow baseball. Seemed like the wrong moment.

The Ohio House

My motel was the Ohio House, on LaSalle Street near River North. It’s one of those mid-century motor lodges that somehow held its ground while everything around it went glass and steel. There are condo towers on every adjacent block that would very much like its real estate. The Ohio House has been sitting there since the 1950s, apparently unbothered by that pressure. Big backlit sign. Parking lot. Rooms with actual parking-lot charm — that specific 1950s American motor court energy where the design hasn’t been updated but somehow that’s the whole point.

I loved it immediately and without reservation.

Dropped my bags, changed my shirt. Walked outside into the warm Chicago evening and just stood there for a second, breathing it in. The city was doing that summer-weekend thing it does — people spilling out of restaurants onto the sidewalk, music coming from somewhere you can’t locate, the El rattling overhead at irregular intervals. The air smelled like exhaust and grilled onions and something I’m going to call possibility because I can’t think of a better word for it.

The First Night in a New City

I didn’t do anything significant that first evening. Walked around River North, got my bearings, found somewhere to eat. An Italian beef place on a side street, the kind with a hand-written menu board and nowhere to sit. Stood at the counter and ate over it the way you’re supposed to. Got the dip. Did not regret it.

Walked down to the Chicago River afterward and stood on a bridge watching the water catch light from the buildings above it. That’s one of my favorite things about Chicago’s river walk — the buildings face it, lean toward it. In most cities the river is the back of the building. Here it’s the front. The city arranged itself to face the water, which is the right call.

Texted a few people I’d landed. Got a drink at a bar where the bartender was reading a novel between orders and didn’t feel the need to make conversation about it, which I respected. Sat there for an hour just watching the city come and go. There’s a kind of solitude that arrives in a big city at night when you’re traveling alone and you chose it — the kind you can end any time you want by walking into the next place, but you don’t, because the sitting-still part is actually the thing you needed.

Doesn’t feel like lonely. Feels like free.

What the Next Three Days Were Going to Be

I had three days in Chicago before the Empire Builder would carry me west. Three days to eat and explore and let the trip find its rhythm before the train changed everything. The plan was loose on purpose. Some neighborhoods I wanted to see — Boystown especially, since the whole premise of this trip is showing up in queer spaces and paying attention. Some food I wanted to try. A few museums if I felt like it, none if I didn’t. Nothing so scheduled it felt like work.

Loose was the right call. It usually is.

Back at the Ohio House, I spread a paper map across the bed. Traced the route with my finger: Chicago to the Pacific Northwest by train, then the coast, then east through the heartland. Thousands of miles. A country I’ve lived in my whole life, about to show me things I hadn’t seen yet.

I had no idea what I was in for. I mean that in the best possible way.

Turned off the light. The city outside was settling into its night register — distant siren, a car horn, someone laughing somewhere below. The El went by once more, its sound rising and fading in that particular Chicago way.

Tomorrow, Chicago.

Tonight the anticipation was enough.