Chicago sports history: 10 worst teams ever, including 2012 Chicago Cubs

Chicago Cubs
Credit: David Banks-USA TODAY Sports

The city of Chicago has had its fair share of amazing championship seasons over the last 40 years. Everything from the Chicago Bears in 1985 and the Super Bowl Shuffle to the Chicago Cubs ending their 108 year World Series drought in 2016, to the Chicago Blackhawks dynasty run during the 2010’s, winning three Stanley Cups in six years.

Unfortunately, there have been a lot of bad seasons in between, especially of recent memory. The 2024 Chicago White Sox are on pace to be the worst team in baseball history, currently with a record of 21-58 and they are on pace to only win 40 out of 162 games but with the rest of their season to be determined, they are an honorable mention of worst seasons by a Chicago sports team for now.

With that in mind, this list will cover the 10 worst seasons of all time by Chicago sports teams. Apologies in advance to the fan bases of the Bears, Bulls, Blackhawks, White Sox and Cubs for triggering some bad memories.

Related: Worst MLB teams ever: 2024 Chicago White Sox chasing history, worst MLB teams of all time

10. 1932 Chicago White Sox

1932 Chicago White Sox
Credit: Brett Davis-USA TODAY Sports

Chicago White Sox pitching was a disaster

MLB: Chicago White Sox at Atlanta Braves
Credit: Brett Davis-USA TODAY Sports

9. 2018-19 Chicago Bulls

Chicago Bulls' Kris Dunn
Credit: Quinn Harris-USA TODAY Sports

Coaching was fatal flaw for 2018-19 Chicago Bulls

NBA: Indiana Pacers at Chicago Bulls
Credit: David Banks-USA TODAY Sports

8. 2023-24 Chicago Blackhawks

Chicago Blackhawks
Credit: Gary A. Vasquez-USA TODAY Sports

7. 2012 Chicago Cubs

Chicago Cubs
Credit: Charles LeClaire-USA TODAY Sports

6. 1962 Chicago Cubs

MLB: New York Mets at Chicago Cubs
Credit: David Banks-USA TODAY Sports

1962 Chicago Cubs offense was non-existent

MLB: NLDS-St. Louis Cardinals at Chicago Cubs
Credit: Dennis Wierzbicki-USA TODAY Sports

5. 2016 Chicago Bears

Jay Cutler, Chicago Bears
Credit: Robert Deutsch-USA TODAY Sports

Losing hurt the 2016 Chicago Bears

NFL: Chicago Bears at Detroit Lions
Credit: Raj Mehta-USA TODAY Sports

4. 2003-04 Chicago Blackhawks

NHL: Chicago Blackhawks at Dallas Stars
Credit: Jerome Miron-USA TODAY Sports

3. 2022 Chicago Bears

Chicago Bears
Credit: Wm. Glasheen/USA TODAY NETWORK-Wisconsin / USA TODAY NETWORK

2. 2000-01 Chicago Bulls

NBA: Chicago Bulls at Miami Heat
Credit: Jasen Vinlove-USA TODAY Sports

1. 1969 Chicago Bears

NFL: Minnesota Vikings at Chicago Bears
Credit: Mike Dinovo-USA TODAY Sports
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