Question of the Day: Who will win Chicago’s next championship?

The City of Chicago holds deep pride in its sports teams. This is despite the fact that each franchise within the City has had a history of inconsistent success, at best.

However, if anyone has been paying attention recently, Chicago sports may be on the verge of a renaissance.

• As we all know, the Chicago Bears have a talented young team that threatened an NFC Championship berth for the first time since 2010.
• The Chicago Bulls have found an exciting Head Coach and General Manager combo to help lead a young/talented roster that recently added fourth overall pick, Caleb Wilson.
• The Chicago Cubs are on track to make a second consecutive postseason, with one of the most electric young players in Pete Crow-Armstrong leading the charge.
• The Chicago White Sox have surprised many by leading the AL Central 90 games into the season, sporting an exciting young core of Miguel Vargas, Colson Montgomery, and Munetaka Murakami.
• The Chicago Blackhawks continue to stockpile talent, and have improved their record in each of the last two seasons and have playoff aspirations in 2026/27 during Connor Bedard’s age 21(!) season.
• The Chicago Sky have been wheeling and dealing, turning over the roster dramatically after down years, and despite a poor record (and injuries) in 2026, a core of Kamilla Cardoso, Gabriela Jaquez, and Rickea Jackson looks promising.
• The Chicago Fire sits third in the MLS standings through 14 contests, led by Hugo Cuypers’ 13 goals.
• The Chicago Stars have had a difficult 2026 season after finishing last in the league in 2025. They currently have a 3-9 record.

Of the 8 professional sports teams in Chicago, an argument could be made for 7 of them having their arrow pointing up. Which got me thinking – could Chicago sports be a few years away from multiple championship contenders?

Which Chicago sports franchise will win a championship next?

This is a Chicago Bears blog, and I truly think that the Bears are poised to win a championship next among these teams. However, I am going to zag and make an argument for the….Chicago Bulls?

Look – I will take any and all grief thrown my way for choosing one of the two Jerry Reinsdorf franchises. Reinsdorf, the owner of the White Sox (until 2029-2033 when Justin Ishbia plans to take over) and Bulls, is not known for prioritizing winning, or more accurately put – spending.

With that said, his franchises have won in the past despite him, so while he may not be a reason they win, he is also not a complete roadblock either. As long as there are butts in seats…

My reason for choosing the Bulls is simple: the NBA is fully of parity at the moment. No other league can come close to sporting the distinction of 8 different teams in the last 8 years. The reason to me is clear – there aren’t any megastars like LeBron James, Kobe Bryant, or...