Art Fairs Are a Long Game: How to Know You’re Ready + Stacking the Deck

Before I ever showed my work at an art fair, I went as a viewer. Between 2015 and 2019, I visited EXPO CHICAGO and the LA Art Show. Both were massive, and honestly, intimidating. There were hundreds of artists showing incredible large-scale work, working with galleries, and presenting themselves more professionally than I had ever seen artists present themselves. I was new to all of it. Things were different back then, too.

That experience gave me a glimpse of what an art fair can be, but it didn't mean my first fair had to look like that. When I finally participated in one in New York in 2024, I chose CLiO Art Fair. It was smaller, the cost was within reach for me, and it was happening in New York City during Fashion Week. I also knew enough people in the city to give myself a real chance of selling work.

What an art fair actually offers

An art fair is a business, whether it's large or small. Some fairs care more about curation and vetting than others, but every fair has to make money to keep going. That's not a bad thing. It's just important to understand the transaction: you pay the fair, and the fair gives you an opportunity to put your work in front of a lot of people. It doesn't guarantee sales.

I think that can be a fair trade. But you can't show up assuming the trade will automatically work in your favor. You need a plan, and you need to work that plan. This is where the business of art really kicks in: knowing where to spend, where to save, and what you want to get out of the experience.

How do you know if you're ready?

You don't need to feel completely fearless, have a gallery behind you, or make the biggest work in the room. I would ask myself: Can I afford the full trip, not just the booth? Do I have work I can transport and price with confidence? Do I know who I can invite, and am I willing to talk to people about the work? And if sales are slower than I hope, will the exposure and relationships still make sense for my practice?

Those questions matter more to me than whether I feel like I've finally “made it.” A fair can be a step in building your practice, not a final exam you have to pass.

Count the whole cost

For New York, I had to pay for flights and ship my work to and from the venue. I needed money for food and getting around, too. And, of course, I wanted room to shop. It was New York Fashion Week after all. My brother lives there, so I could save on a place to stay.

Take inventory of every expense before you commit. Booth costs are only one line in the budget. Travel, shipping, lodging, meals, local transportation, and the cost of making your work all count. Once you see the full picture, you can decide where to cut costs without cutting the opportunity. Always look for ways to save.

Bring your people with you

I told everyone I knew in New York, from close friends to people I hadn't seen in a while. Inviting people you know does two things. First, someone who already knows, likes, and trusts you may be more likely to buy. Second, familiar faces can give you momentum when you're doing an unfamiliar thing in an unfamiliar place.

The financial buy-in can make the stakes feel high. You don't want nerves or overwhelm to get in your way before you even start a conversation. Having people you know in the room can help you feel like you belong there, because you do.

Make the work fit the opportunity

For that first fair, I made a moderate number of works that were fairly priced and easy to transport. A few people who were already interested in buying from me came to the fair. That approach helped me sell art, make a splash, and show the gallery and fair supporters that I was serious.

It's tempting to think you need huge pieces with huge price tags to look impressive, or that the right collector will walk in and buy a $25,000 painting. That might happen for somebody, but I wouldn't build my first-fair plan around it. Think about what your audience can actually take home, what you can afford to move, and how you want people to experience the work in person.

Stack the deck, then play the long game

Artists spend money learning what works. Putting your work into the market can burn cash before you understand which opportunities are right for you. I'm not saying to shrug off a big financial loss. Do what you can to avoid wasting money. But don't judge a fair only by what happens at the register that weekend, either. Showing art in person, outside of the Instagram feed and beyond your usual city or even country, can build relationships and possibilities for your practice over time. It's a long game.

My next big fair is The Other Art Fair in Chicago. I chose it because it caters to artists working independently, outside the grip of a gallery. Chicago also means something personal to me: I went to college there, and I have family and connections in the city. I'm putting the same lessons to work again. I want greater exposure in Chicago, a way to save on costs like lodging, and a real shot at making the fair profitable.

If you're considering your first art fair, don't ask only whether you're good enough to be there. Ask whether this particular fair fits your work, your budget, your people, and the next step you want to take. Then stack the deck as best you can and show up ready to connect.

You got this.

-Von