Chicago's Top 100 Annual Events

Matthew WoodBen RubensteinMolly EachWendy WollenbergStacy WardenAmalie DruryJenny Berg

July 7, 2008

The Children's Place Association's 'Once Upon a Time ' gala

The Children's Place Association's \"Once Upon a Time\" gala

Photo: Courtesy of the Children's Place Association

Chicago may be synonymous with certain high-profile events, such as the Taste, the auto show, and the marathon, but the city also plays host to various big ticket benefits, industry-leading trade shows, and trendsetting art and fashion events. Here are our picks for the most crowd-pleasing, buzz-generating, money-raising, press-getting annual events in Chicago.Art, Architecture & Design Events

Benefits

Fashion Industry Events

Festivals

Parades, Walks & Holiday Events

Sports Events

Theater, Dance & Music Events

Trade Shows & Conventions

2025 Industry Innovators Article Image Experiential2 B

Industry Innovators 2025: 11 Experiential Experts Reinventing How We Experience Brands

The XP Agency has worked on events for brands like Procter & Gamble, Netflix, Coca-Cola, and Ghirardelli.

Industry Innovators 2025: Tamara Francois and Adolfo Vasquez

Rose Gold Collective handled Don Q Rum's festival build at the Country Bay Music Festival in Miami.

Industry Innovators 2025: Sarah Sebastian

'One of the most defining moments of my career was leading the creative direction for Hewlett Packard Enterprise’s HPE Discover event keynote, the first-ever corporate keynote at Sphere in Las Vegas—a landmark moment in both creativity and technology,' says Saaud.

Industry Innovators 2025: Sami Saaud

Brands & Event Pros

Industry Innovators 2025: 11 Experiential Experts Reinventing How We Experience Brands

Meet the boundary-pushers, rule-breakers, and big thinkers shaping the future of experiential marketing.

2025 Industry Innovators Article Image Experiential2 B

Brands & Event Pros

Industry Innovators 2025: Tamara Francois and Adolfo Vasquez

The co-founders of The XP Agency see every touchpoint as an opportunity to connect—long before the event begins and long after it ends.

The XP Agency has worked on events for brands like Procter & Gamble, Netflix, Coca-Cola, and Ghirardelli.

Brands & Event Pros

Industry Innovators 2025: Sarah Sebastian

The owner and creative director of Rose Gold Collective brings a boutique mindset to bold brand moments.

Rose Gold Collective handled Don Q Rum's festival build at the Country Bay Music Festival in Miami.

Brands & Event Pros

Industry Innovators 2025: Sami Saaud

The founder and chief creative officer of No Filter Creative blends fine art, branding, and technology to push the boundaries of immersive storytelling.

'One of the most defining moments of my career was leading the creative direction for Hewlett Packard Enterprise’s HPE Discover event keynote, the first-ever corporate keynote at Sphere in Las Vegas—a landmark moment in both creativity and technology,' says Saaud.

Brands & Event Pros

Industry Innovators 2025: Ryan Coan

The founder and CEO of Creative Riff has been chasing creative curiosity since his dorm room startup days, now leading bold activations for some of the world’s biggest IPs.

Brands & Event Pros

Industry Innovators 2025: Mia Choi

The founder and president of MAS leads with inclusion, imagination, and a refusal to coast—turning events into meaningful, memorable moments.

'Every event is an opportunity to get wildly imaginative—and we take it,' says Choi.

See Inside This High-Tech, Multisensory Experience from Don Julio

How U.S. Event Planners Can Navigate Global Attendance Challenges

C2 Montreal 2025: How the Business Conference Puts Creativity in 'Motion'

This Event Turned Home Decor Into a Celebration of Latinas' Life Moments

How BET’s Stylish Anniversary Dinner Honored the Past—and Embraced the Future

What's New in Meetings and Trade Shows: MPI WEC Heads to St. Louis, New Trends Report Shows Corporate Events on the Rise, and More

Brands & Event Pros

Industry Innovators 2025: Katie (Limle) Fiore

The head of production for Crown & Conquer is passionate about creating experiences that feel real, relevant, and rooted in culture.

Crown & Conquer is a creative agency that works with major brands on live experiences, content, and partnerships. Recent work includes Coca-Cola's eye-catching activation at Coachella 2025.

Brands & Event Pros

Industry Innovators 2025: Jimmy Knowles

The global head of experiential marketing for Canva is turning brand experiences into global celebrations of creativity, community, and joy.

Brands & Event Pros

Industry Innovators 2025: Dwayne Guzman Barnett

The executive vice president of 15|40 Productions aims to craft experiences that merge technology, creativity, and community in groundbreaking ways.

15|40 is a creative-led marketing events agency specializing in experiences and integrated activations for global brands; the team regularly works on activations at major events like D23 (pictured).

Brands & Event Pros

Industry Innovators 2025: Dana Darley Dailey

The senior manager of whiskey portfolio events for Heaven Hill Brands is redefining brand activations through the art of “hospitality by design.”

'One of my favorite career moments was hosting an immersive product launch dinner in our rickhouse as part of our grain-to-glass series,' says Darley Daily.

Brands & Event Pros

Industry Innovators 2025: Ajith Krishnankutty

The vice president of experiential marketing for Capital Group is reimagining events as data-driven, tech-forward experiences—with human connection at the core.

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Brands & Event Pros

Industry Innovators 2025: 9 Event Tech Leaders Defining What’s Next

Meet the minds behind the tools, platforms, and ideas revolutionizing how events are executed in 2025 and beyond.

2025 Industry Innovators Article Image Event Technology

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