Sometimes it can be a struggle to be a fan of Chicago professional sports teams because they're typically not good but when they finally do win it's an amazing experience.

When Did Chicago Pro Sports Teams Last Win Championships?

I was talking with one of my friends a couple of days ago and of course, the subject was sports in Chicago. We were discussing how bad the teams are right now. It's not even fun watching. The only one with any glimmer of hope is the Bears.

READ MORE: Do The Chicago Bears Owe Illinois Football Fans Money?

Out of the big four of sports (NFL, MLB, NBA, and NHL), the last to win a championship was the Cubs in 2016. My buddy was telling me that his grandson doesn't remember the Blackhawks being good. He explained to him that they were great and won three Stanley Cups in five years. The last was in 2015.

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It doesn't seem that long ago but I guess it really was. For Chicago, championships come few and far between. No wonder so many kids from Illinois cheer for teams that aren't from here. It's a lot more fun to back a winner.

Close-up on raised hands holding trophy against blue sky

How long has it actually been since my favorite sports teams in Chicago won a championship? Well, I did a little research to find out. I'm warning you, it's very depressing if you're a fan.

  • Chicago Bears - Super Bowl 1986 (NFL championships 1921, 1932, 1933, 1940, 1941, 1943, 1946, & 1963)
  • Chicago Cubs - World Series 2016 (1907 & 1908)
  • Chicago White Sox - World Series 2005 (1906 & 1917)
  • Chicago Blackhawks - Stanley Cup 2015 (1933, 1937, 1961, 2010, & 2013)
  • Chicago Bulls - World Champions 1998 (1991, 1992, 1993, 1996, & 1997)

Choose Chicago

LOOK: 50 images of winning moments from sports history

Sometimes images are the best way to honor the figures we've lost. When tragedy swiftly reminds us that sports are far from the most consequential thing in life, we can still look back on an athlete's winning moment that felt larger than life, remaining grateful for their sacrifice on the court and bringing joy to millions.

Read on to explore the full collection of 50 images Stacker compiled showcasing various iconic winning moments in sports history. Covering achievements from a multitude of sports, these images represent stunning personal achievements, team championships, and athletic perseverance.

Gallery Credit: Peter Richman