What To Expect At The 2026 Cubs Convention This Weekend

Chicago sports fans have a lot in store for them this weekend. The Chicago Bears are playing in the NFL playoffs on Sunday night, and the 2026 Cubs Convention will be underway on Friday at the Sheraton Grand Chicago.

This year, the convention is likely to carry more emotion than in previous years. The 10th anniversary of a World Series championship team, the unveiling of new Cubs, and the passing of a legend are sure to do that.

It has been 10 years since the Cubs' legendary World Series run ended their 108-year drought; this year is expected to draw tons of fans because of it.

A 2016 World Series Reunion is coming to Cubs Con!

Join us: https://t.co/sty4G5JzwE pic.twitter.com/IwlG9qwa3u
— Chicago Cubs (@Cubs) December 19, 2025

What Should Cubs Fans Expect This Weekend?

The 2016 Cubs reunion will likely be the biggest draw of the weekend. After all, it was the biggest moment for the team and their fans in the last century-plus.

The Cubs recently announced who will be attending from the championship team. Albert Almora Jr., Trevor Cahill, Chris Coghlan, Carl Edwards Jr., Dexter Fowler, Justin Grimm, Jason Hammel, Kyle Hendricks, Jason Heyward, John Lackey, Jon Lester, Miguel Montero, Mike Montgomery, Anthony Rizzo, Pedro Strop, Matt Szczur, Travis Wood and World Series MVP Ben Zobrist are all expected to be at the convention.

The Cubs will also announce which former players will make up this year's class of Cubs Hall of Fame inductees. It seems likely, given the timing of the event, that at least a couple of 2016 players could be wearing blue jackets by the end of the weekend.

Turning back the clock to reminisce with the players who were part of this team will be something fans will not want to miss.

While basking in the past, and maybe doing some Harry Carayoke in between, the team will also celebrate the present and future of Cubs baseball, with fans getting a first look at the 2026 Cubs roster.

New Chicago Cubs third baseman Alex Bregman at the United Center | Kamil Krzaczynski-Imagn Images

This will include seeing new additions Alex Bregman and Edward Cabrera for the first time in Cubs threads.

Bregman signed with Chicago to a five-year, $175 million contract, one of the richest in Cubs history, and should play a huge role in the 2026 lineup. As for Cabrera, the Cubs traded away their top prospect, Owen Caissie, to acquire the star pitcher.

Sadly, the Cubs lost a legend in 2025 in Ryne Sandberg. The Hall-of-Fame inductee passed away from cancer at the age of 65 last July, and will be sorely missed by the organization and fans. Former Cubs such as Rick Sutcliffe, Shawon Dunston, Bobby Dernier, Jody Davis and Andre Dawson will remember their teammate. Tears will surely be shed at this part of the event.

Cubs legend Ryne Sandberg rookie card — A Ryne Sandberg rookie card | Thomas J. Turney/The State Journal-Register / USA TODAY NETWORK via Imagn Images

From reliving the epic World Series to remembering a legend, this is sure to be an emotional roller coaster for Cubs fans.

2026 Cubs Convention info

Dates: January 16-18, 2026

Location: Sheraton Grand Chicago Riverwalk

Experiences: Autograph signings, Harry Carayoke, Auctions, Cubs Bingo, Cubs & Wrigley Field Exhibits, Youth Baseball Clinic, and more.

Conversations: Updates from Jed Hoyer and Carter Hawkins, a sit-down with Craig Counsell, appearances by Ian Happ and more.

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