1. Expo Chicago

This international exhibition of contemporary and modern art kicks off the fall art season. Held in Navy Pier’s Festival Hall, the 2019 event showcased work from some 135 exhibitors representing more than 25 countries. To get the lay of the land—the event spans more than 170,000 square feet—visitors can join 60-minute tours of the expo, led by museum educators and other arts professionals. Around 38,000 art lovers attend the expo each year. Next: September 2020
Photo: Justin Barbin
2. NeoCon

Billed as the most important event of the year for the commercial interiors industry, NeoCon is now in its 51st year. Held at the Mart, the event showcases industry trends and features keynote presentations from design-industry influencers. There’s also an exhibit hall highlighting approximately 300 companies. Next: June 8-June 10, 2020
Photo: Courtesy of NeoCon
3. SOFA

Up from #4
The gallery-presented art fair focuses on three-dimensional artworks in a variety of categories. An average of 35,000 attendees browse wares from some 80 dealers, and sales are estimated at $15 million to $20 million per show. In 2018, the event featured a new floor plan that allowed for increased signage visibility and easier walkability for guests. Next: October 31-November 3, 2019
The gallery-presented art fair focuses on three-dimensional artworks in a variety of categories. An average of 35,000 attendees browse wares from some 80 dealers, and sales are estimated at $15 million to $20 million per show. In 2018, the event featured a new floor plan that allowed for increased signage visibility and easier walkability for guests. Next: October 31-November 3, 2019
Photo: Wittefini
4. Old Town Art Fair

Up from #5
Taking over the Old Town Triangle historic district, the fest showcased roughly 250 artists and drew about 30,000 attendees this year. Along with browsing through drawings, paintings, photographs, ceramics, and more, guests could participate in a Garden Walk, check out live music, or entertain their little ones in a “Children’s Corner.” Next: June 13-14, 2020
Taking over the Old Town Triangle historic district, the fest showcased roughly 250 artists and drew about 30,000 attendees this year. Along with browsing through drawings, paintings, photographs, ceramics, and more, guests could participate in a Garden Walk, check out live music, or entertain their little ones in a “Children’s Corner.” Next: June 13-14, 2020
Photo: Courtesy of Old Town Art Fair
5. 57th Street Art Fair

Up from #6
The Midwest’s oldest juried art fair has been running for 72 years. Held in Hyde Park, near the Chicago home of former President Barack Obama, the fair draws more than 20,000 attendees. Guests get to meet the artists behind handmade works including painting, ceramics, photography, and sculpture. Typically, the fair exhibits work from about 200 artists. Next: June 6-7, 2020
The Midwest’s oldest juried art fair has been running for 72 years. Held in Hyde Park, near the Chicago home of former President Barack Obama, the fair draws more than 20,000 attendees. Guests get to meet the artists behind handmade works including painting, ceramics, photography, and sculpture. Typically, the fair exhibits work from about 200 artists. Next: June 6-7, 2020
Photo: Courtesy of 57th Street Art Fair
6. Open House Chicago

The Chicago Architecture Center hosts this free public festival, which offers rare, behind-the-scenes access to some 250 local buildings in more than 30 neighborhoods. Participants can explore skyscrapers, historic mansions, private offices, and more; an online itinerary tool can help guests plan their days. Next: October 19-20, 2019
Photo: Report Photography
7. Design Chicago

The Midwest’s largest residential design conference typically draws around 2,500 attendees. This year, the two-day event featured 175 presentations as well as 52 open houses, 79 product debuts, and 33 programs geared toward continuing education. Next: Fall 2020
Photo: Courtesy of Design Chicago
8. AIA Chicago Designight

Roughly 1,000 industry pros, including architects and engineers, flock to this gathering at Navy Pier. Hosted by the Chicago chapter of the American Institute of Architects, the 2018 event doled out 33 Design Excellence Awards in categories such as Interior Architecture and Divine Detail. Next: October 25, 2019
Photo: Wittefini
9. International Interior Design Association's Black Tie Gala

Held annually during NeoCon, this event honors the winners of two prestigious industry competitions: the annual Interior Design Competition and the Will Ching Design Competition. This year, the event celebrated its 25th, or silver, anniversary and had shimmering, metallic decor to match. Next: June 7, 2020
Photo: Christopher Dilts
10. Hyde Park Art Center Gala

The center’s largest annual fund-raiser helps support its mission: To assist contemporary artists in every phase of their careers. The evening is interspersed with so-called “Artist Interventions,” which allow guests to interact with performance artists, search for a hidden pop-up speakeasy, or even get tattooed. The 2018 gala raised $500,000. Next: November 22, 2019
Photo: Tran Tran
11. U.S. Green Building Council—Illinois Chapter's Limelight

Sustainability pros return to this event year after year to network with industry leaders. In 2019, the event took over Venue Six10, where some 400 attendees partook in drinks, bites, and raffles. The event also features the Emerald Awards Ceremony, which recognizes achievements in green building, design, and technology in Illinois. Next: May 2020
Photo: Courtesy of U.S. Green Building Council Illinois Chapter