Nearly 200 leaders from Chicago’s tourism, hospitality, cultural, and events industries gathered at 360 CHICAGO on June 16 for the latest All for the Love of Chicago Roundtable, titled “Sleigh the Season” and focused on one of the city’s greatest opportunities for future visitation growth: winter tourism.

Building Momentum for Winter 

Choose Chicago Chief Marketing Officer Lisa Nucci welcomed attendees and emphasized the importance of planning for the winter season now, while partners still have time to align campaigns, strengthen partnerships, and identify new opportunities to attract visitors.

Nucci noted that winter represents one of Chicago’s largest tourism growth opportunities, highlighting that increasing overall annual visitation during the season by just 1% would translate into approximately half a million additional visitors and significant economic impact for local businesses, hotels, restaurants, attractions, and cultural institutions.

She also unveiled a major new initiative designed to drive future travel demand: a first-of-its-kind partnership between Choose Chicago and Amazon that will feature Chicago as the exclusive bookable destination during Amazon Prime Day Travel Deals, running June 23-26.

Through the promotion, Amazon Prime members will have access to discounts of 20% or more at participating Chicago hotels, with bookings available through the first quarter of 2027. The initiative will place Chicago in front of millions of consumers during one of the world’s largest online shopping events and represents a significant investment in generating future visitation, particularly during the winter months.

Choose Chicago President and CEO Kristen Reynolds also welcomed attendees, underscoring the opportunity to grow Chicago’s tourism footprint during the winter season and encouraging partners to continue working together to elevate the city’s profile as a year-round destination with everything to offer travelers during the winter season.

What Makes Chicago a Winter Destination 

The morning’s featured conversation was moderated by Judy Hsu, anchor at ABC 7 Chicago, and explored the experiences that make Chicago a truly distinctive winter destination.

Panelists included Liz Gilbert, Vice President of Sales & Marketing, The Magnificent Mile Association; Bria Purdiman, Director of Communications, Chicago Department of Cultural Affairs and Special Events (DCASE); and John Collins, Executive Director, Goodman Theatre

The panel discussion highlighted the powerful combination of beloved traditions, cultural programming, and new visitor experiences that continue to attract travelers throughout the winter season.

Gilbert shared updates on the Wintrust Magnificent Mile Lights Festival, discussing its continued evolution as one of the Midwest’s premier holiday events and emphasizing the opportunity to attract visitors well beyond the traditional holiday period.

Purdiman discussed the city’s growing portfolio of winter programming, including the collaborative effort between DCASE, ABC, and Choose Chicago that helped bring Dick Clark’s New Year’s Rockin’ Eve to Chicago. She also previewed several upcoming activations and events planned for the season ahead.

Collins reflected on the enduring popularity of Goodman Theatre’s annual production of A Christmas Carol, which returns for its 49th year this winter, and highlighted the role Chicago’s cultural community can play in positioning the city as an attractive winter destination.

Together, the panel reinforced that Chicago offers visitors experiences they cannot find anywhere else—from the Magnificent Mile Lights Festival, Christkindlmarket, ZooLights at Lincoln Park Zoo, and the City of Chicago’s holiday celebrations to seasonal favorites such as Chicago Restaurant Week and Chicago Theatre Week, which activate neighborhoods and drive visitation during the winter months.

Collaboration Drives Results 

As with every All For The Love of Chicago Roundtable, collaboration remained at the center of the conversation.

During the event’s popular “hot mic” segment, partners from across the tourism and hospitality community shared updates on upcoming events, attractions, campaigns, and opportunities for cross-promotion.

The key takeaway from the morning was simple: Chicago has the assets and the infrastructure to be a leading winter travel destination. By aligning our messaging and working together to tell a compelling story about the city’s seasonal experiences, we can attract more visitors, fill more hotel rooms, support more local businesses, and continue building momentum year-round.

Thank You to Our Partners 

  • 360 CHICAGO, for hosting the Roundtable and providing exceptional hospitality.
  • Kehoe Designs, for creating the event’s festive staging and décor.
  • Blue Plate, for catering the event.
  • Show Ready Productions, for A/V equipment and services.
  • Sugar Bliss, for providing holiday-themed treats for attendees.

Thank you to everyone who joined us. Together, we’re helping ensure Chicago remains a destination that is Never Done. Never Outdone.