Chicago sports teams: Who’s on top?

Chicago is known for its fierce sporting heritage and culture. Horse racing betting may not be at large in Chi city with our climate not lending itself well, but we have teams in all of the big four sports. Over the last century, The Windy City has welcomed some of the greatest athletes of all time and created dynasties that will live forever in the hearts of Chicago Natives. Of course, the most memorable of them all are the Bulls team of the 90s. With pillar-to-pillar stars including Dennis Rodman, Scotty Pippen and the GOAT himself Michael Jordan, coach Phil Jackson recorded two threepeats between 91-93 and 96-98, dominating an entire era of basketball. They also played host to arguably the biggest upset in MLB history, when in 1906 the Chicago White Sox defeated inter-city rivals the Chicago Cubs 4-2 in the World Series. 

Six Stanley Cups and a Super Bowl win means that they are one of just four US cities that have won championships in all four major sports. Although we are now eight years removed from the most recent success, when the Chicago Cubs won the World Series in 2016, there is no lack of talent of present. Let’s take a look and compare the successes and potential of Chicago sports teams.

Chicago Bulls

The Chicago Bulls have not quite hit the heights of that Phil Jackson team of the 90s in recent times. They have only reached the playoffs once in the last six seasons, losing 4-1 in the opening round of the 2022 season to the Milwaukee Bucks. That is not to say there is no talent on their current roster however with the likes of DeMar DeRozan, Nikola Vucevic and Zach Lavine among their ranks. At worst, they look in line to make the play-in tournament for a second consecutive season. As of writing they are the 9th seeds in the Eastern conference with a comfortable lead over the 11th seeded Brooklyn Nets and a finish in the top 10 looks all but wrapped up. The Bulls of today are a farcry from the legends of the 90s but there is enough talent to build around for a stronger future.

Chicago Blackhawks

One of the more recent success stories for Chicago sports, the Chicago Blackhawks took home the Stanley Cup for the sixth time in franchise history back in 2015. That roster was full of stars with the likes of Jonathan Toews, Duncan Keith and Patrick Kane winning multiple championships in Chicago. The Blackhawks of present however have some way to go if they want to match them. As of writing, they are the second worst team in the NHL, winning just 18 of their 66 games placing them rock bottom of the central division. There is still reason to be excited for the future however when looking at youngster Connor Bedard. The 18-year-old leads the roster for goals, assists, points and ice-time among forwards and should he deliver on the promise he has shown is a clear building block for any future success for the Blackhawks.

Chicago Bears

The Chicago Bears have struggled for consistency since the 90s with their only Super Bowl success coming in 1985. They would reach the promised land again in 2007 in a losing effort to the Indianapolis Colts and since then have only reached the playoffs three times. Their 7-10 finish in 2023 was an improvement on the previous season, but the performances throughout highlighted deficiencies in their offense. There are still question marks surrounding Justin Fields’ position as the starting quarterback and with the number 1 overall pick in the 2024 draft they could be ready to anoint Heisman Trophy winner Caleb Williams as QB1. That, along with a number 9 overall pick and a very healthy $62 million available in cap space means that a completely revamped Bears roster in 2024 gives fans every reason to be excited for the near future.

Chicago Cubs

In 2016, the Chicago Cubs ended the longest drought in all major sports leagues when they won the World Series for the first time in 108 years. They followed this triumph up with strong performances, reaching the playoffs in three of the next four seasons. However, they have not made an appearance since, finishing 2023 very poorly to miss out once again. Heading into 2024, the infield combination of shortstop Dansby Swanson and second baseman Nico Hoerner are one of if not the best duos in the league. There is no doubt enough talent there to at least drag them into the playoffs, but their underperformance in 2023 must be put behind them.

While the Bulls are the best performing team among the big four sports in Chicago, it looks like the Bears have the most to be excited about. Two early picks in the first round and plenty of cap to manoeuvre around means they can rejuvenate their roster in 2024. The Windy City is without a major championship in nearly a decade, but we could see that change soon should all go well for the Bears.