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Become a subscribing EarlyWork member to view this event and get access to our monthly newsletter with our picks of the most exciting things to explore in the art world and other creative industries, along with two in-person gatherings per month, exclusive works from emerging artists, early access to available works from partner galleries, tickets to select Gertie and partner events, and more.
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An insider cultural experience in Chicago that supports the future of curatorial practice and artist-driven exhibitions. Across the cultural sector, traditional institutions are struggling—stretched thin by administrative bloat, mission drift, and a disconnect from the communities and creators they were built to serve. At a time when art’s role in society is more vital than ever, we need new models. Ones that are more agile, more personal, more impactful—and more true to the spirit of art itself.
Join a curated group of 40 other adventurous travelers, culture lovers, creatives, thinkers and collectors from around the world for an immersive week exploring the hidden gems of Chicago’s art world. You’ll gain rare access to artists, galleries, and curators shaping the city’s creative landscape—while actively supporting the exhibition at the center of it all.
At the heart of the experience is Over My Head: Encounters with Conceptual Art in a Flyover City, 1984-2015, a major new show that spotlights the relationships between Chicago’s dealers and the artists they championed—many of whom went on to shape global conversations in contemporary art. It’s a show about freedom, risk, and the often-invisible infrastructures that allowed artists to thrive. The same ethos drives this experience.
Participation in this experience directly funds the exhibition. A portion of every ticket supports the production of Dealer’s Choice, its curators, and its public programming. After our private preview, the show will open to the public—free of charge.
This is the first in a series of intimate, high-touch cultural journeys across cities. We’re meeting people where they are—offering meaningful access to the art world in ways that are immersive, story-rich, and rooted in real relationships. Whether you’re a longtime patron or simply someone who wants a smarter, more soulful way to engage, you’re invited.
This is not a gala. It’s not a fair. It’s something more personal.
Come to experience culture. Stay to be part of shaping it.
Pricing does NOT include flight or accommodations. Room blocks with discount available.
Extremely limited capacity. Chicago is just the beginning—we may be coming to your city next.
FULL EXPERIENCE + NIGHT BEFORE
Add a plus-one for $5000
FULL EXPERIENCE
Add a plus-one for $4500
EARLYWORK MEMBER PASS
Must be an EarlyWork member with annual membership to claim. Become a member ➝
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SATURDAY DAY PASS
SUNDAY DAY PASS
FULL EXPERIENCE + NIGHT BEFORE
Add a plus-one for $5000
FULL EXPERIENCE
Add a plus-one for $4500
EARLYWORK MEMBER PASS
Must be an EarlyWork member with annual membership to claim.
—
SATURDAY DAY PASS
SUNDAY DAY PASS
ALREADY A MEMBER?
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Includes the complete itinerary from our opening dinner through the week’s cultural programming: behind-the-scenes access, private visits, immersive conversations, and curated gatherings across the city.
Includes everything in the Full Experience, plus a private musical performance & an original Artist Edition
Available to EarlyWork members only.
For the busy traveler or the person whose schedule is packed to the brim months in advance and can only fit one day in… You will experience half of the full experience! Join us for one day on Saturday or Sunday — each day will be full of amazing experiences, meals and conversations.
