Derek Nielsen Photography

Derek Nielsen Photography

Uncategorized Chicago Old Town Art Fair Best In Show – Photography
Photograph of Derek Nielsen as the 2023 winner of the Old Town Art Fair for Best In Show

Chicago’s Old Town Art Fair is one of the most prestigious art fairs in the United States. With over 200 nationally acclaimed artists and an estimated 30,000 plus attendees, Old Town has been voted the #1 art show for several years. The unique setting in Chicago’s near Northside neighborhood has all the ingredients for a great art show. In addition to the art, the weather is usually ideal, the food and music are fantastic, and the garden walk completes the experience. This is the must-see fine art fair for serious collectors, art lovers, or someone just looking for something fun to do. 

Were Is The Old Town Art Fair

Each year, the art fair occurs in the heart of the historic Old Town Triangle District. The southern border is Menomonee Street, while its northern border is Wisconsin. From East to West, the boundary streets are Lincoln Park West and Orleans. The nearest gate to the city is the south gate, which is located in North Park. For those less familiar with the city, this entire area is located just West of Chicago’s famous Lincoln Park. The largest cross streets are North Avenue and Clark Street. 

Is The Art Fair Free?

Image of art collectors walking through a crowded Old Town Art Fair in Chicago

Yes, the show is free, but a $12 donation is recommended to help the association put on such a wonderful event. Children are free. The donation also supports local schools, arts, and culture programs and helps preserve the area’s historical architecture. 

What Makes Old Town Art Fair The Best Show?

Image of Old Town Art Fair in Chicago and Derek Nielsen's photography booth in front with people walking through the streets

There are so many reasons this show is revered again and again as one of the top art fairs in America. I’ll go ahead and explore a few. 

  • People come for the art, so it has to be top-tier. This pool of jury-selected artists travels from around the United States to attend. Half of the exhibiting artists need to reapply each year, keeping the competition extremely high. 
  • The setting is in such a beautiful neighborhood. Beyond the gorgeous tree-lined streets of Chicago, many homes are historically charming. 
  • Live music is one of Chicago’s strengths, and this show brings in some great artists to add to the experience. 
  • Food…any great show needs food and drink to add to the social experience. The food court or various food vendors serve up Chicago classics like hotdogs, pizza, and tacos. A variety of beer and wine help wash it all down as Goose Island Brewery and several vineyards supply the drinks. 
  • The Children’s Corner is full of children’s activities like face painting and interactive, hands-on arts and crafts. 

Booth requirements for Old Town

Image of Derek Nielsen's best in show winning booth at Old Town Art Fair
All fine art images are available through Derek’s website.

First of all, you need to provide your own booth for the show or rent one. If you rent one, you have to be able to set it up yourself. This art fair does not allow rental companies to set up artist booths. I purchased a Trimline art booth. Despite the high price tag, this is the perfect booth for displaying at any art fair. First of all, Trimline art booths are durable. For me, this is a must. I am not about to risk losing tens of thousands of dollars of luxury fine art photography if bad weather arises. Booths must be under 9 feet tall. With this in mind, I encourage getting the adjustable height tent. Future art shows won’t have the same requirements, so you will have extra space to display your work if needed.

How To Apply To The Show

By following the link on the Old Town Art Fair’s website, you are taken to ZAPP. Through ZAPP, an artist can see all the entry requirements. To enter the show, artists must submit five images of their work to an independent jury of art professionals. Over 700 artists apply for 176 spots, with 44 exempt from winning in previous years or for other reasons. Over half of the exhibiting artists must reapply each year to ensure variety and create the best experience for the attendees. 

Early to mid-January is the application deadline, and by February 1st, the artist will be notified of the results. By March 1st, the booth fee of $750 ($100 additional for corner booths) must be paid in full.

The Old Town Garden Walk

Charming house in Old Town Chicago

Something unique to this show is that the surrounding neighborhood opens its properties to attendees to see its beautiful gardens. It is a great way to meet people, enjoy a beverage, and potentially network. Many of the houses are funky and charming. My booth was across from this adorable yellow house that looked like it should be on Cape Cod instead of Chicago.

Winning Best In Show At The Old Town Art Fair

Derek Nielsen holding up his best in show ribbon at the Old Town Art Fair while standing in his booth

As a fine art photographer, I knew the Old Town Art Fair was one of the country’s best, if not the best, art fairs. In light of this, I applied seven years in a row only to be denied. I was either submitting the wrong images for jurying, which is something young artists need to practice, or I was not inspiring the judges with my work. Regardless, I applied for an eighth time and was finally accepted. It was my first time showing here and, I was nervous but also wanted to bring it. I bought the best art boothdisplay panels, lighting, and decorations. When someone entered my booth, I wanted them to think they were in a high-end gallery, not an art fair. The quality of the prints always takes people’s breath away, and I needed a booth to compliment the work. 

Opening Day Of The Show

​The set up for the show takes place on Friday. The booth looked incredible, and I was so anxious to begin conversations about my work. Now, it was time to open Saturday early in the morning. I made every little adjustment to my booth and waited for people to start walking by. Because I am also a passionate conservationist, traveler, and lover of all things wild, I wanted to talk to every person who peered into my booth. This may have been something the jury committee was looking for, but it was just me being me. It breaks my heart to see an artist pour their heart and soul into their work only to sit with their arms crossed in the back of their booth, waiting for someone to buy something. Get up! Sell yourself! Be passionate!

Awards Sunday

Saturday was exhausting but worth every minute. I had a blast talking about my passions. Sunday comes around, and I go over to the artist’s lounge to grab a cup of coffee. It was a cold, misty morning, so it was nice to get something warm. On my way out, I noticed a group of people getting ready to hand out ribbons to the various winners of the show, including best in show for the overall event.

Not 5 minutes later, the judges came by my booth, the whole group of them, and I heard a woman’s voice say, “Derek Nielsen?” “Yes,” I replied (certainly expecting I had done something wrong). She says, “We would like to inform you that you have been selected for Best In Show for the category of photography, but we also wanted to let you know that you were the top-scoring artist for the entire show. 

​My Wave Of Emotions Winning One Of The Best Festivals

As someone who applied year after year to get into the show, I was certainly surprised to win it on my first appearance. When the jury surrounded me with the news of my coming in first, I couldn’t help but be overcome with emotion. This was the first time in my professional career as a photographer a jury of my peers recognized me with distinction. Tears came to my eyes as I thanked and hugged every single person. Pride filled my soul, and I just wanted to scream at every person who ever doubted me or told me, “Good luck with being an artist.” A blue ribbon middle finger to you, haha. It felt great. 

One of the best parts was hanging that blue ribbon up in my booth for the day and having people walk by with added interest, knowing my booth was the winning booth. I will never forget that day as long as I live. This is a reminder to all of you not to give up. Don’t let self-doubt win. I felt like a failure seven years in a row before feeling the bliss of winning it all. Remember your why, and focus on your passions. 

Inside Tips For Artist Attending Old Town

Artist Derek Nielsen practicing setting up his booth before a show in Chicago
  • Practice setting up your booth twice before attending to iron out all the kinks in your setup.
  • Be prepared for wind and rain. The last thing you want is to damage your precious art investment due to being unprepared for the weather.
  • Spend a little extra money on lighting and decorations. Present your booth as professionally as you can.
  • Take names, emails and phone numbers of any interested buyers. Once they leave your booth you may never hear from them again.
  • Bring a friend or family member to help if you don’t have an assistant. Have them rehearse the details of your work. So many people come into your booth it is nice to have a helping hand.
  • Bring food and drinks to keep your energy high. It is two very long days of being on your feet selling yourself.
  • DON’T SIT IN THE BACK OF YOUR BOOTH ARMS CROSSED. Be friendly. Sell your passion. Sell yourself to potential buyers. Make it fun for everyone.

Fall In Love With Art And Have Fun Doing It

As art festival season begins in the Northern Hemisphere, go out and support your artist friends and family. I can’t tell you how much it meant to me to have so many people I care about showing up to my booth to support me. I truly appreciate all my fans, followers, and collectors. Without you, my message for and support for conservation would be nonexistent. Thank you from the bottom of my heart. For other interesting topics around fine art photography, travel, or conservation, check out my other articles.

Derek with a penguin

Hello! I'm Derek.