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Thursday September 24 · Travel guide

An athlete wrote to me a few months ago, worried about his goal pace. We spent twenty minutes on that. And forty on how he'd get from the airport to his hotel, where he'd pick up his bib, and what he'd do with cold hands waiting in the corral.

The second conversation turned out to matter more than the first.

Today it's the format we used for the Bogotá Half, the one you asked me to repeat. If you're travelling to Chicago from outside the US, this saves you surprises.

This isn't something you improvise the week before.

If your country is in the Visa Waiver Program — Spain, Chile and most of Western Europe — you need an ESTA at least 72 hours ahead. File it weeks out, and only on the official US government site. Third-party sites charge absurd fees for the same thing.

If you travel on a B1/B2 visa — Colombia, Mexico, Argentina and others — check that it's valid for at least 6 months past your return date, not your arrival. That mistake is more common than you'd think, and it surfaces at immigration.

On cash: the US runs almost entirely without it. Card, Apple Pay or Google Pay covers 95% of everything — Expo, trains, restaurants, shops. Carry $50 to $100 in cash only for emergencies.

Both airports connect to downtown on the CTA train network, known locally as the L.

🏨 Where you sleep decides how far you walk

And how much stress you bank before a 26.2 mi (42 km) race:

My advice: if it's your first Major and the budget allows, pay for proximity. Walking 40 minutes with race nerves before sunrise isn't free.

October in Chicago is famously variable. Historical start temperatures run from 39 °F to 57 °F (4 °C to 14 °C), and Lake Michigan adds a wind that feels colder than the thermometer says.

You'll enter the corral between 6:00 and 7:30 depending on your wave, and the wait outside can run over an hour.

This is where experience shows: bringing old or cheap throwaway clothing — sweatshirt, blanket, gloves, hat — isn't a luxury. Keeping your extremities warm reduces glycogen cost and needless muscular tension in the opening miles. The organisers collect all of it for donation, so toss it guilt-free.

The Expo runs Thursday to Saturday at McCormick Place. There are free shuttles from downtown, and the Metra Electric train from Millennium Station goes straight there.

Go Thursday afternoon or early Friday. Avoid Saturday. Walking a giant expo for hours the day before drains the legs more than almost anyone expects — and you won't feel it until mile 20, when there's no fixing it.

On food: this isn't the moment for deep dish or heavy meat. Save that celebration for Sunday night, when your digestive system no longer has to answer for anything. Pasta, white rice, potato, bread. And book restaurants weeks ahead, because they fill with runners who had the same idea.

On course there are 20 aid stations, roughly every 1.5–2 mi (2–3 km), with Gatorade Endurance in the first cups and water after. If you didn't train with that formula during your block, bring your own.

Reach the security entrance 90 to 120 minutes before your corral officially closes. The only bag allowed in is the clear plastic one you get at bib pickup.

Your watch distorts between miles 12 and 14, crossing the heart of the Loop. Don't trust instant pace there: run on feel and use the painted markers on the road.

🧳 What a trip like this actually trains

We talk about running here because it's the medium I know. But this applies just as well if yours is open-water swimming, a gran fondo, a triathlon or a tournament in whatever sport: travelling far to compete tests things that appear in no training plan.

A language you don't command. A city you don't know. Sleeping badly in someone else's bed. Eating differently. And that uncomfortable sense of controlling nothing around you, hours before the thing you've prepared for months.

That's why this guide exists. Not so you memorise train times, but so you take off the table every decision that can be made in advance. What's left, then, is the only thing worth deciding that day: how you're going to run.

And that reaches well past sport. We rarely fail for lack of capacity. We fail from the wear of deciding at the wrong moment things we could have decided calmly.

Tomorrow, the checklist: 30 items so nothing gets forgotten. See you then.

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