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Chicago Bears quarterback Caleb Williams (18) celebrates a 25-24 win against the Washington Commanders on Oct. 13, 2025, at Northwest Stadium in Landover, Maryland. Â Â Â Â Â Â Â Â Â Â Â Â Â John J. Kim/Chicago Tribune/TNS
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From double doinks, dropped fly balls, slow rebuilds and greedy billionaires these last few years have been pretty rough for Chicago sports fans. With the Chicago Cubs being eliminated from the playoffs at the hands of division rival the Milwaukee Brewers there will be no major sports title for the 9th straight year in the city of Chicago. In that span Chicago has seen a total of 12 playoff appearances and only 2 playoff series wins both by the Cubs. They have also had a total of 8 top-five draft picks since then. It’s time to take a deep dive at each team’s last couple of seasons to see if after all these tough years are things finally trending upward or will we be talking about another disappointing year this time again next year.Â
Bears:
At the start of the 2017 season the Chicago Bears selected quarterback Mitchell Trubisky out of the University of North Carolina with the 2nd overall pick hoping he would be their next franchise quarterback. After a pretty underwhelming rookie season the Bears hired Matt Nagy as their new head coach and things looked promising in 2018 Trubisky and the Bears had won their first division title since 2010. But unfortunately Bears fans know how that season ended… In 2020 the Bears made their 2nd playoff appearance in the Nagy era and it ended the same way the last one did a first round exit. In 2021 it was time for a QB change as the Bears drafted Justin Fields from Ohio State with the 11th overall pick. In 2022 it was time now for a coaching change this time the Bears hired Matt Eberflus hoping he would be the one to fix the Bears. In 2024 the Bears took Heisman winner Caleb Williams while also making history by firing coach Eberflus midseason the first time in franchise history. Now in 2025 the Bears have offensive guru Ben Johnson leading the charge by changing the culture in Chicago with many fans believing the Bears have entered a new and exciting era.
Bulls:
The Bulls used to be the face of the NBA at one point but as of late they have fallen out of relevance as they have had 8 losing seasons in the last 9. It looked like things were finally starting to click for the Bulls in 2021 as they had a historic start to the season but after a key injury to Lonzo Bal the season derailed and the Bulls just barely made the playoffs but as most teams in Chicago they had an early exit. They have now since moved on from that 2021 core and have made some trades that have helped this team get younger in hopes of building a contending team once again.
Cubs/Sox:
Moving to the baseball side of things the Cubs and Sox have both had their fair share of struggles since 2017. For the Cubs they tried to defend their title but lost to the Dodgers then followed that up with an early exit in the 2018 playoffs. In 2021 they decided it was time to hit the reset button and trade away some key pieces of their 2016 world series win. Despite the Cubs playing well the last couple of seasons some fans believe that their ownership is holding them back from getting back to the promised land.Â
The White Sox looked like they were ready to become a competitive team with a really young roster and many of those young guys signed some pretty big extensions and after just two playoff appearances in 2020 and 2021 it blew up as many players faced many injuries and just struggled to stay on the field. In 2024 the White Sox broke the record for most losses in a single season and became a laughing stock of the league. However the Sox were able to turn the page in 2025 and despite a losing season the future is starting to look bright for both the Northside and Southside.
Blackhawks:
After an exciting dynasty from 2010-2015 the Hawks had a couple of playoff appearances in 16 and 17 but they were all early exits. Since then the Blackhawks have been trying to replicate that magic from 10-15 but it’s been taking some time that fans have begun to grow impatient after having 5 consecutive losing seasons. The Blackhawks were awarded the number one overall pick in 2023 and they selected their first puzzle piece of the new era Connor Bedard. It’s been a pretty slow rebuild but in the second half of last season and after a coaching change to start the 2025-26 season things have started to look better but they are still a couple of years removed from getting back to the team they once were in the early 2010s.
 It’s been hard for sports fans in Chicago but there is a lot to look forward to in the next couple of years. Will we finally be able to talk about how amazing it is to be a sports fan in Chicago or are fans ready to be heartbroken once again only time will tell.
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