CHICAGO STYLE | City Cruises Live! Chicago Bears Cruise

Up Close with the 2006 Legends Aboard City Cruises Live! Chicago

CHICAGO–The City Cruises Live event, celebrating the unforgettable 2006 Chicago football season, delivered more than skyline views and highlight reels. It was a once-in-a-lifetime chance to truly connect with the icons of that historic team.

Hall of Famer Brian Urlacher, quarterback Rex Grossman, and defensive standout Alex Brown weren’t just on board—they were in it with fans for nearly every moment of the one hour VIP Access Meet-n-Greet PLUS the three-hour dinner cruise.  Whether grabbing personal photos, swapping high-fives, or diving into detailed Q&As, these legends made sure no fan went unnoticed.

From the moment VIP boarding began, the players mingled effortlessly, sharing memories, cracking jokes, and answering questions that had clearly been burning in fans' minds for years.

Urlacher lit up as he recalled his favorite moments—under stadium lights and off the field.

“I really enjoyed hanging with the guys for lunch in the office - they were family - my home away from home,” he shared with profound reflection.  “We used to play dodgeball in the locker room—offense vs. defense. Trash cans as goals. It got intense,” he said with a grin.

Alex Brown, all smiles all night, said it best:  “We practiced hard, but we always kept it fun.  “I felt 14-years-old the entire time I played. That’s how I approached the game,” as he looked over at a young kid in the crowd and reminded him to always have fun!  The same mantra he shares with his own kids.  “Enjoy it; however, if you want to be great - BE GREAT - TikTok isn’t going to get you there.”  He went on to share some personal moments with his own son’s love/hate relationship with regimented workouts, alongside his Champion father, while pursuing his own dreams.  “It wasn’t easy, but he wanted it enough - you have to want it!”

Brown also gave a vulnerable glimpse into his pregame mindset—always nervous - always wanting to make his family proud each and every time.  “Mariah Carey got me through it,” he admitted, laughing. “I’ve always used music to calm me down to get into the right mindset.”

Rex Grossman was candid and charismatic, sharing what it meant to play in Chicago. “Most people don’t get to experience what I did here,” he said. “If I played today, I’d want to lead the Bears under this current coaching staff.   He went on to express deep care and introspection when speaking about how he and the players felt about each other, and the utmost respect they had for Coach Lovie Smith as a father figure.

“We didn’t want to disappoint him or each other,” Brown added.

Both he and Grossman credited the leadership of Urlacher for the team’s success; “There was no better Hall of Famer to play beside.”

Fans asked it all—and got real, thoughtful answers back.  Not rushed, not rehearsed. Every interaction felt personal, because it was. And even Jeff Joniak, the night’s host, shared a gem—like the time he accidentally pocket-dialed Urlacher, who still picked up the late night call - showing his true character as a caring person and exemplary leader, both on and off the field.

This cruise didn’t just celebrate champions—it celebrated fathers, teammates, and the work it takes to become great.  The resounding message  - it was family - and these legends treated the City Cruises Live crowd like their own.

Where live entertainment meets the water, experience intimate events featuring musical artists, sports legends, TV personalities, and more. Throughout the summer, guests can enjoy unique cruises such as Randy Houser Live and Country Cruisin’ with Colt Ford on Lake Michigan.  Additionally, Chicago sports fans can look forward to special Chicago White Sox cruises such as its 2005 Chicago White Sox World Champions Cruise with A.J. Pierzynski & Teammates, and Chicago Bears-themed cruises A Night with Chicago Football Conference Champions: Brian Urlacher, Rex Grossman & Alex Brown offering exclusive experiences and VIP opportunities with team legends. 

Visit www.citycruises.com/chicago for upcoming dates.