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As I write this blog post, I’m sitting at Gate C20 at Chicago’s O’Hare Airport. Everything I originally packed is still in my jacket—though now, it’s also holding some swag from the Deep Dish Swift conference:

• Drawstring backpack
• 2 x playing cards
• Popcorn
• Mini-fruit candies
• Stickers and pins
• T-shirt
• Duolingo Hat
• Socks

The conference T-shirt and Duolingo hat? The T-shirt is layered under my Wool & Prince shirt, and I’m wearing the hat. Everything else fits into the two large front pockets of the Uniqlo Utility Short Blouson Jacket.

Next to me is a Loews Hotel laundry bag holding a Giordano’s takeout pizza box. That’s right—I’m bringing back some Chicago deep-dish pizza from the dinner I organized right after the conference ended. That dinner completed my tour of three of the most well-known deep-dish pizza spots in Chicago. Last year, I visited Pequod’s. Earlier this trip, I stopped by Lou Malnati’s after the Cubs–Phillies game at Wrigley Field. Of the three, Giordano’s deep-dish was my favorite. Pequod’s had too much dough. Lou Malnati’s was a little watery (from the tomatoes) and smaller in portion.

Giordano’s Meat Lover’s and Classic deep-dish pizzas best matched my mental model of what deep-dish should be—thick as pies and stuffed with toppings, cheese, and crust—based on my experience at Bay Area Chicago-style spots like Zachary’s, Pizz’A Chicago, and Patxi’s Pizza.

The pizza box is bulky, and it made me realize: I’m bringing back more pizza than luggage.

Back in the Bay Area

I’m back home now and have had time to reflect. Overall, it was another successful zero-baggage, no-luggage trip. I recently learned there’s even a term for it: “flying naked,” popularized by a Thrillist article in December 2024. Packing-wise, I think I did well. Here’s a breakdown of what worked, what didn’t, and what I’ll tweak for next time.

Clothing

The Uniqlo jacket was a solid choice—more stylish than the Scottevest hoodie I’d considered, and it carried the same amount of gear. My only complaint: when carrying larger items like the iPad mini, the bulge is very noticeable in the outer pockets. I’m tempted to learn how to sew so I can add a hidden back pocket big enough to conceal it.

Only on the first day did I wish I had brought an extra shirt. Sitting in the Wrigley Field bleachers was a bit chilly in the wind. Otherwise, the Wool & Prince shirt performed well in the hotel and during my early morning runs. I’ve noticed a few small holes forming in the back; they’re not obvious when the shirt is tucked in, but they may soon relegate it to backup status. I wore the 100% merino wool tee. Wool & Prince now sells a Signature Crew Neck T-Shirt made with 78% merino and 22% nylon for more durability.

The Bluffworks Ascender Chinos in khaki also held up well. They’re wrinkle-resistant but not wrinkle-free. After five days, they’ll need a quick iron before their next outing.

I washed my socks and underwear nightly, and they were dry by morning. I did the same for my running shorts after each workout.

Here’s a video from my first night at the Loews Hotel showing my washing routine:

The belt was optional, but I might explore adding low-profile pouches to it and go partial-Batman. They could hold bulkier items like the Anker charging brick or the MagGo, worn at the back where the jacket would conceal them.

Toiletries

Since I was in Chicago for five days but only four nights, I had one extra piece of floss. The razor came in handy on day two. With my long hair, the brush was essential. I missed my electric toothbrush—it’s clearly more effective—but I used my phone to set a two-minute timer each night (30 seconds per quadrant) while I brushed with my half-height toothbrush.

Tech

I debated between the Anker MagSafe MagGo UFO 3-in-1 charger and the Anker 67W Prime Charger. I ended up bringing the MagGo, and it worked fine. Once I checked into the Loews, it stayed in the room. I brought the charging brick to the conference room in case I needed to top off my iPhone or iPad mini during sessions.

What I could have benefited from was a longer USB-C cable. The 6-inch cable I brought was just a bit too short. A longer one would have offered better strain relief and allowed both the MagGo and my devices to lay flat on a table more comfortably.

Another item I debated bringing was the iPad mini, but I’m glad I did. Demoing MixEffect and RouteEffect was much better on the iPad mini—especially since I had set up Remote Webview to stream the output from my ATEM 2 M/E Constellation HD at home directly into MixEffect. This let me show off the popular SuperSource animations and how RouteEffect can manage routing between the Constellation and my Videohub 20×20 12G.

On day one, I typed notes in Apple Notes using the onscreen keyboard. On days two and three, I switched to the 2nd-gen Apple Pencil. The experience felt better than last year—I suspect some improvements in iPadOS 18 over 17—but it still doesn’t feel as natural as writing on the old Apple Newton. Maybe it’s time I resurrected my WriteHere Newton app for the iPad?

I had nowhere to store my iPhone during runs, and I wasn’t about to carry it. So I tracked my routes using my Apple Watch Ultra. As for the hotel keycard, I slid it under my orthotic soles inside my running shoes. Didn’t feel a thing.

I used my AirPods Pro a few times—mainly for FaceTime calls and podcasts on the flights. During the conference, they stayed in the hotel room.

Miscellaneous

The ESR for MagSafe Wallet held my driver’s license, credit card, and some cash. During the trip, it gained a few receipts and a Chicago Ventra card. Once I got the card, I quickly moved it to Apple Wallet on my phone. Not every retailer accepted Apple Pay, so I ended up using my physical credit card a couple of times.

The Vapur collapsible water bottle came in handy on the first and last days. It stayed in the hotel room during the conference, since there were plenty of beverages provided. When collapsed, it’s compact enough to stash in a pocket, so I plan to bring it again on future zero-luggage trips.

While I handed out a few, I didn’t go through all of my stickers. I’ll be bringing the rest to WWDC next month to share with other indie developers. If you see me at my Pre-WWDC gathering in San Jose on Saturday, June 7, 2025, ask me about my packing strategy and get a sticker!

Up Next: Spokane, Washington

Next week, I’m “flying naked” again—this time to Spokane, Washington. Since it’s not a work trip, I’ll pack even lighter, meaning no iPad mini. The weather looks similar to Chicago and the Bay Area, with no rain in the forecast. I’ll swap the T-shirt for a nicer Wool & Prince dress shirt, and I may go with black chinos instead of khaki. The Uniqlo jacket is versatile enough to earn another round.

Product Links

• ESR for MagSafe Wallet, Strong Magnetic Wallet for iPhone, Phone Wallet with Adjustable Stand
• Small belt pouches on Amazon
• Bluffworks Ascender Chinos
• Uniqlo Utility Short Blouson Jacket
• Wool & Prince Signature T-Shirt
• Wool & Prince 100% Merino T-Shirt
• Apple Pencil (2nd generation)
• AirPods Pro (2nd generation)
• Anker MagSafe MagGo UFO 3-in-1 charger
• Anker 67W Prime Charger

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