The Q4 edition of the SITE Chicago Newsletter celebrates a season of connection, growth, leadership, and giving back — highlighting signature events, Young Leaders momentum, member milestones, and an exciting look ahead to 2026.

Holly Trolley 2025: “’Twas a Groovy Night!”

SITE Chicago’s 11th Annual Holly Trolley, a three-time award-winning holiday tradition, brought together Chicagoland’s incentive professionals for an unforgettable evening of festive networking and celebration. Guests cruised the city on themed trolleys featuring disco vibes, holiday cocktails, delicious bites, and live entertainment, with exclusive stops at Allium by Blue Plate and Wrigley Field’s 1914 Club. The night buzzed with energy, collaboration, and community spirit, made possible by dedicated volunteers and an incredible lineup of sponsors.

Young Leaders: Connecting & Giving Back

SITE Chicago’s Young Leaders Committee continued to thrive in 2025 with curated programs designed to foster connection and professional growth. Highlights included a highly successful Young Leaders Co-Workday at Convene’s Monroe Street location, featuring breakout sessions on cross-generational networking, strategic gifting, and an engaging panel discussion. New Young Leaders Receptions launched ahead of major chapter events, helping first-time attendees build confidence and connections — with more planned in 2026, including the annual Feed My Starving Children volunteer event.

Education & Membership Milestones

Education remained front and center with engaging programs focused on contracting, negotiation, and professional development. SITE Chicago closed 2025 with a record-setting membership year, nearing 300 members — a testament to the strength, relevance, and momentum of the chapter. New initiatives like SITE Circles offered smaller, interactive virtual meetups that deepened member connections and will continue into 2026.

Traveling Will Takes the Spotlight

Meet Traveling Will, SITE Chicago’s ambassador and ultimate travel companion. From coast to coast — and beyond — Will represents teamwork, fun, and the spirit of SITE Chicago, popping up in photos from member travels worldwide. Members are invited to take Will along on future adventures and share his journey.

Leadership Reflections & the Road Ahead

Outgoing President Nancy McFadyen, CIS, reflected on a year of record-setting events, educational growth, and strong volunteer leadership across Illinois, Michigan, and Wisconsin. Incoming President Kelly Fuller shared her vision for 2026 — maintaining high-impact programming while streamlining processes, strengthening infrastructure, and continuing to deliver exceptional value to members.

What’s Next in 2026

SITE Chicago heads into 2026 with a dynamic slate of events, including:

• Annual General Meeting – January 29, Chicago
• Young Leaders Feed My Starving Children – February
• Michigan, Wisconsin & Chicago networking events
• Summer Education Meeting & Grand Slam Baseball Event
• Fall Education & CSR programs
• 12th Annual Holly Trolley – December 1, 2026

Partner With SITE Chicago

Sponsorship opportunities for 2026 are now available, offering meaningful ways to engage with SITE Chicago’s growing and energized community.

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Date/Time: July 31, 2026 | TBD
Location: Wrigley Rooftop | Chicago

SAVE THE DATE!

Details to follow!

Time & Location

July 31, 2026

Time & Location

Thursday, July 30
Time: TBD
Chicago

The event includes an introduction to Pickleball play for beginners. There will be pickleball play for all levels. Network with SITE Chicago/Wisconsin travel incentive professionals.

Come check out the private event space and pickleball courts at Brookfield’s premier pickleball club.  Join us for a fun evening of pickleball play,  raffles, door prizes, lite bites & drinks!! 

Time & Location

Date: Thursday, June 25
Time: 4:00 p.m. to 6:00 p.m.
Location: ACE Pickleball Club, Brookfield, WI

Time & Location

Date: Wednesday, April 22
Time: 4:00 p.m. to 7:30 p.m.
Location: Cafe Brauer, Chicago

Date: Tuesday, April 7, Chicago
Time: 4:00 p.m. to 7:00 p.m.
Location: The Field Museum, Chicago

Date/Time: March 11, 2026 | 5:00 p.m. to 7:00 p.m.
Location: New Holland Brewing Co | Grand Rapids, Michigan

REGISTRATION OPEN!

Get ready to mix, mingle, and celebrate the luck of the Irish,SITE Chicago style. Our 3rd Annual Shamrock Social is headed back to Grand Rapids, and you won’t want to miss this high-energy evening designed to connect, inspire, and celebrate the incentive travel community.

This event is FREE for planners and open to incentive travel professionals who want to expand their network, share ideas, and build meaningful relationships, all while enjoying great cocktails, lively conversation, and a festive St. Patrick’s Day vibe 

Time & Location

March 11, 2026

Time – 5:00 p.m. to 7:00 p.m. 

Click on the link below for the event details to put on the page.

Time & Location

Thursday, February 26
Time: TBD
Schaumburg

The Q3 edition of the SITE Chicago Newsletter highlights a season filled with community, education, and connection.

Grand Slam 2025

On August 1st, SITE Chicago hosted its 4th Annual Grand Slam at the Wrigley Rooftops. Over 215 hospitality professionals gathered for a day of baseball, networking, and prizes. Attendees enjoyed a Cubs win, a gifting experience by Joycoast, raffles, and grand prizes including trips to Tucson, the Bahamas, and Buenos Aires. The celebration wrapped up with an afterparty at X-Golf Wrigleyville, sponsored by Hilton Luxury BrandsQ3-2025-site-chicago-newsletter.

Young Leaders Spotlight

The Young Leaders Committee hosted another successful Co-Workday on June 9 at Convene’s Monroe Street location. Nearly 30 attendees joined for breakout sessions on cross-generational networking, gifting trends, and industry insights, along with a panel discussion moderated by Taylor Smith (Meetings Today) featuring leaders from Maritz, NHS Global Events, and DeloitteQ3-2025-site-chicago-newsletter.

Summer Highlights

• Summer Education Event – Focused on contracting and negotiation under the theme “Deal or No Deal,” with interactive panels and candid discussions.
• Wisconsin Flamingle (June 17) – A lively networking night with raffles, gifts from Magnolia Bath & Soap Company, and bites from Old Republic Surety CompanyQ3-2025-site-chicago-newsletter.

Community Spotlight: Supporting Dana Weaver

SITE Chicago rallied around Dana Weaver, a former chapter president, after his diagnosis of Primary CNS Lymphoma. A private Facebook support group has been created to share encouragement, photos, and stories as Dana undergoes treatmentQ3-2025-site-chicago-newsletter.

Meet Traveling Will

SITE Chicago introduced Traveling Will, the chapter’s new mascot and biggest fan. Will represents teamwork and fun, traveling alongside members to industry events worldwide. Keep an eye out—he might pop up anywhere from Austria to Aruba!Q3-2025-site-chicago-newsletter

What’s Next

Upcoming events include:

• September 17 – Wisconsin Networking at Blu (Pfister Hotel, Milwaukee)
• October 20 – Fall Education Event, Union League Club, Chicago
• October 22 – Michigan Rooftop Mixer, The Godfrey Hotel
• December 2 – 11th Annual Holly Trolley Holiday Celebration

CLICK HERE to download the complete issue.

SITE Chicago Q2 2025 Newsletter Recap

The latest SITE Chicago Newsletter is full of updates, opportunities, and upcoming events for members across Illinois, Michigan, and Wisconsin.

New Website

SITE Chicago has launched a brand-new website featuring event details, membership information, and resources for hosted planners. Visit the site to explore.

Sponsorship & Membership Opportunities

• Sponsorship packages are available for upcoming events, including Young Leaders programs.
• SITE Global is offering a free one-year membership for FICP planners.
• The Member Get a Member program (May 1–31) rewards both new and referring members with $100 discounts.

Save the Dates

Mark your calendar for these 2025 events:

• June 9 – Young Leaders Co-Work Day (Chicago, IL)
• June 17 – Milwaukee Mixer (Brookfield, WI)
• June 25 – Summer Educational Event (Salon 61, Chicago, IL)
• July 31 – “Grand Slam” Warm-Up (LuxBar, Chicago)
• August 1 – Cubs Rooftop Game + After Party
• September 17 – Milwaukee Networking (Pfister Hotel)
• September 19 – Detroit Shop & Sip (Faircloth Boutique)
• December 2 – Holly Trolley (Chicago, IL)

Young Leaders Spotlight

Meet the committee driving SITE Chicago’s Young Leaders program:

• Brittany Cerrillos – VP, Motivation Excellence
• Bridget Radzicki – Destination Consultants
• Preston Krzyzak – Soundings
• Taylor Smith – Meetings Today
• Morgan McCracken – Maritz Global Events

CLICK HERE to download the complete issue.