Windup Chicago 2025 Recap: A Growing Fair and a Few Firsts

This past weekend marked Windup Watch Fair’s fourth time in Chicago. After years of attending the New York edition of the watch retail show, I was curious to see how the Midwest version compared. Windup Chicago has a reputation for being more laid-back and less crowded than its coastal counterparts, but that may be starting to shift. The crowds were larger this year, and the overall mix of presenting watch brands felt more varied—both in scale and in identity.

I went Friday and returned Saturday with my family, which was a fun way to experience the show. We walked the floor together, compared favorites, and my mom continued her streak of buying something at every Windup she attends (this time the limited Casio Ring Watch).

Across both days, a few standout watches kept pulling me back—some familiar, some unexpected. And one big-brand booth hinted at how Windup might continue evolving down the line.

Watch Highlights

A few pieces really stood out to me over the course of the weekend. One of the big highlights was the DOXA SUB 300 Carbon Aqua Lung US Divers Sharkhunter. This watch isn’t new, released in 2020, but seeing it in person reminded me why it’s such a compelling piece. It’s a limited edition of 300 with the iconic Aqua Lung logo—Jacques Cousteau’s diving gear company that dates back to the 1940s. The forged carbon case is cool enough, but the forged carbon dial really takes it up a notch. You don’t see many dials made from forged carbon, and the yellow accents on this one pop perfectly against the matte black case. It just looks right. Oh—and it weighs just 85g, strap and buckle included.

Another fun sighting was over at the eBay booth, where they had a vintage Seiko 62MAS—the very first Seiko dive watch. It even had its original box (which I meant to get a picture of… and forgot). Still, very cool to see one in that kind of sharp case condition.

One surprise brand I really enjoyed spending time with was Mühle-Glashütte, a German tool watch maker I hadn’t seen in person before. They specialize in nautical watches and their best-known model is likely the S.A.R. Rescue-Timer (pictured above). A few design details immediately stand out: the black rubber surrounding the bezel and capping the bracelet’s center links, the curved 'Nautische Instrumente' dial text, the 4 o’clock crown, and the matching 4 o’clock cyclops over the date. It’s one of those watches where you can tell the decisions were driven by function, but the end result still feels cohesive.

That rubber, in particular, is a smart touch. The bezel ring and bracelet inserts are made from a durable, soft-touch rubber that offers some added protection. I bonked my SKX on a machine at the gym today—metal on metal—and couldn’t help but think of this rubber-bezeled Mühle-Glashütte from yesterday.

Is Chicago Still the “Chill” Windup?

In my preview writeup, I wrote about Windup Chicago’s reputation as the more relaxed, less jam-packed version of the fair compared to New York or San Francisco. That reputation still holds up, but it’s shifting.

On Saturday, there was a line out the door hours after the show opened. I spoke with Zach Weiss (Executive Editor and Chief Creative Officer at Worn & Wound, the team behind Windup), and he echoed the same thought: Windup Chicago has always been the smaller, more laid-back show—but this year saw more brands and visitors than ever. Several brand owners told me the same thing. Attendance is clearly growing, and while that’s great to see, it does make me wonder: will the fifth Windup Chicago need a bigger venue?

That’s not to say it felt overcrowded. Venue West, which has hosted all four editions of the show so far, handles the traffic well with its single-level open floor plan. But if this year’s growth is any indication, Windup Chicago might be entering a new phase.

A New Kind of Brand Mix

One other thing worth mentioning: C.D. Peacock, a Chicago-area jeweler, had a booth at the fair—and they brought along some major Swiss brands like Tudor and TAG Heuer. This was the first time I’ve seen brands of that size and reach at Windup, especially ones that play in the same price tier as many of the independents exhibiting just a few feet away.

The booth was packed. A lot of people were clearly excited to try on Tudors in particular—getting hands-on with newer models like the METAS-certified Black Bays. It brought a different kind of energy to the show floor.

What made this setup especially interesting is that these Swiss brands and the typical Windup exhibitors aren’t just close in price—largely sitting well within the sub-$5,000 range—they also compete in similar categories: tool watches like divers, GMTs, and field watches. Seeing them side by side didn’t feel out of place, but it did add a new layer to how the show functions. Windup has always been a place where independent brands get the spotlight. This year, that spotlight felt just a little more shared.

Final Takeaways

This year’s Windup Chicago was exactly what I hoped it would be: great watches, great conversations, and some pleasant surprises along the way. Getting to share the fair with family was a personal highlight, but so was being reminded—yet again—just how much there is to learn and love in this hobby. Already looking forward to the next one.