Cubs Convention 2026: A Weekend of Baseball, Memories, and Big-Time Energy in Chicago
Chicago sports fans are in for a dream weekend. With the Bears hosting a playoff game at Soldier Field on Sunday night and the 2026 Cubs Convention kicking off Friday, the Windy City is buzzing.
While the NFL postseason brings the heat, Cubs fans know this weekend marks something just as sacred: the unofficial start of baseball season. Who needs to wait for pitchers and catchers when the Cubs Convention is ready to roll?
This year’s convention promises to be one of the most emotional and memorable in recent history. From debut appearances by new Cubs like Alex Bregman and Edward Cabrera to a heartfelt tribute to the late Ryne Sandberg, the weekend is packed with nostalgia, fresh faces, and fan-favorite traditions.
Let’s break down what fans can expect - and why this year’s Cubs Convention is shaping up to be something special.
Where It’s All Happening
The 2026 Cubs Convention takes place at the Sheraton Grand Chicago Riverwalk, located at 301 E North Water St. This is the annual gathering spot for Cubs fans from all over the country to come together, talk baseball, meet players, and celebrate the past, present, and future of the franchise.
Friday: The Curtain Rises
Convention Registration (12p - 8p, Riverwalk Level)
First things first - check in.
This is where you grab your welcome packet and lanyard, which you’ll need to access panels and events all weekend. It’s your all-access pass to Cubs fan heaven.
Opening Ceremonies (Time TBD, Main Sheraton Ballroom - Level 4)
This is the emotional and energetic launchpad for the weekend.
Expect a packed ballroom, loud cheers, and maybe even a few goosebumps. Fans will get their first glimpse of new additions like Bregman and Cabrera in Cubs gear, and the 2026 Cubs will take the stage alongside legends of the past.
The Opening Ceremonies also include the reveal of this year’s Cubs Hall of Fame inductees - and with the 10-year reunion of the 2016 World Series team on the docket, don’t be surprised if some familiar championship faces are honored.
Off the Mound with Ryan Dempster (7:30p, Main Sheraton Ballroom)
Dempster brings his signature mix of comedy and insight to this late-night-style show featuring guests ranging from current players to front office execs like Jed Hoyer and manager Craig Counsell. It’s a relaxed, entertaining way to wind down after the high-octane Opening Ceremonies.
Harry Carayoke (10p, Sheraton Lobby - Level 3)
Yes, it’s exactly what it sounds like. Grab a drink, belt out your favorite tune, and join fellow fans in honoring the spirit of Harry Caray - one off-key note at a time.
Saturday: Panels, Tributes, and a World Series Reunion
Baseball Operations Update with Jed Hoyer & Carter Hawkins (9a, Main Sheraton Ballroom)
Want to hear straight from the decision-makers?
This panel is for you. Hoyer and Hawkins break down the Cubs’ offseason moves, the state of the farm system, and what to expect heading into 2026.
With the front office making some bold moves recently, there should be plenty of insights to soak up.
Sit Down with Craig Counsell (10a, Main Sheraton Ballroom)
Counsell reflects on his journey so far in Chicago, including his first playoff run as Cubs manager. Expect some behind-the-scenes stories and a look at how he’s shaping the culture inside the clubhouse.
The Compound LIVE with Ian Happ (11a, Main Sheraton Ballroom)
Four-time Gold Glove winner Ian Happ brings his hit podcast to the convention stage.
This live taping is always a highlight, especially with Anthony Rizzo slated to join this year. Happ and Rizzo?
That’s must-see Cubs content.
Cubs Pitchers: On the Mound (12p, Main Sheraton Ballroom)
Jim Deshaies leads a deep-dive conversation with a panel of Cubs pitchers, including Matthew Boyd, Cade Horton, Jameson Taillon, Colin Rea, and Edward Cabrera.
They’ll talk mechanics, mentality, and what it takes to thrive on the bump in today’s game. It’s a fascinating look into the art of pitching.
2016 World Series Reunion (1p, Chicago Ballroom VIII-X)
Ten years later, the magic still lingers.
Ron Coomer sits down with key players from the team that broke the curse, including Anthony Rizzo, Ben Zobrist, Pedro Strop, Miguel Montero, Kyle Hendricks, and Justin Grimm. This panel isn’t just about nostalgia - it’s a celebration of one of the most iconic moments in franchise history.
Cubs Hitters at the Plate (2p, Main Sheraton Ballroom)
Coomer returns to chat with current Cubs hitters like Nico Hoerner, Matt Shaw, Dansby Swanson, and Miguel Amaya.
They’ll break down approach, preparation, and the grind of a 162-game season. For fans who love the chess match of hitting, this is a can’t-miss conversation.
Remembering Ryno (4:30p, Main Sheraton Ballroom)
This will be one of the most emotional moments of the weekend.
Cubs greats Rick Sutcliffe, Shawon Dunston, Bobby Dernier, Jody Davis, and Andre Dawson join Cole Wright to honor the life and legacy of Ryne Sandberg, who passed away last summer. Expect heartfelt stories, laughter, and more than a few tears as the Cubs family remembers one of its most beloved members.
Tom’s Reception (4:30p, Shula’s Steakhouse - Level 3)
Want to ask a question directly to Cubs owner Tom Ricketts?
Here’s your chance. This informal reception is a rare opportunity to hear from the top of the organization in a more personal setting.
Cubs Bingo (7:45p, Main Sheraton Ballroom)
Yes, bingo.
But this isn’t your grandma’s game night. Fans line up early (some as early as 5p) for a shot at prizes like autographed memorabilia and Wrigley Field collectibles.
It’s a fan-favorite event for a reason - the energy is high, the competition is real, and the prizes are worth the wait.
Harry Carayoke (10p, Sheraton Lobby - Level 3)
Round two. If you missed it Friday, here’s your second chance to sing your heart out and dance the night away with fellow fans.
Sunday: For the Next Generation
Youth Baseball & Softball Clinic (9a, Main Sheraton Ballroom)
The weekend wraps with something for the kids - two sessions of clinics designed to teach fundamentals and spark a love for the game. Pre-registration is required, but for young fans, it’s a chance to learn from the pros and get inspired.
More Than Just Panels
Beyond the schedule, there’s plenty to explore throughout the Sheraton. Cubs historian Ed Hartig hosts history-focused exhibits, Cubs Authentics runs auctions with game-used gear, and vendors offer exclusive team merchandise. And of course, autographs are a major draw - with opportunities to meet current players and legends alike.
Whether you're diving into panels, chasing down signatures, or just soaking in the atmosphere, Cubs Convention 2026 is shaping up to be a weekend to remember. With a nod to the past and an eye on the future, it’s a celebration of everything that makes Cubs baseball so special.