Chicago Cubs - Always been my favorite team, and in some odd fashion the fact that they hadn't won a title in so long up until 2016 actually drew me more to them and made rooting for them more fun. Now I just want to see them build a dynasty and make up for that huge world series gap by winning a few more championships.
Chicago Bulls - Of course, the Jordan era is what really won me over, and seeing all those games in the United center both as a kid, and more recently watching the Derrick Rose Bulls dominate most of the east. That was, until they ran into the brick wall that was LeBron's teams and D Rose had his career altering injury :(. Still, the Bulls are probably my second favorite team as I love basketball, probably even more than baseball, but between the Bulls sucking now and the NBA being heavily influenced by officiating, it's tough for me to really get into them these days.
Blackhawks - Have great memories watching many a playoff hockey game with my friends back in the 2009-2015 post-cap dynasty era with Kane, Toews, Hossa, Seabrook, etc. Not a HUGE hockey guy though I do love the excitement and intensity in the playoffs in particular. Hoping the Hawks can recapture some of their former glory and reload next year, though unfortunately they're starting to age.
Bears - more of a casual fan when it comes to the Bears as I'm not really a football fan. Though it would be cool to see them win a superbowl as they're now the only Chicago sports team not to win a championship in my lifetime (just barely missing the 85 superbowl as I was born in late '86)..
Far more recently, I've also been into watching the Overwatch league (if esports count) and root for a couple of teams there -
Houston Outlaws - They've got a prett solid Zen and D.va player, who are two of my favorite characters, Jake's also fun to watch with the Junkrat and Linkzer's a beast with Widow sniping. I also learned that the company that founded them, Optic Gaming, is actually based in Chicago too, only moving to Texas in the last few years. Of course if Chicago ever gets a real OW team I'll root for them over Houston but for now, Outlaws are my team.
Shanghai Dragons - Like the fact that they have the only female in the league in Geguri, who comes with an inspirational story. And of course, I'm just pulling for them to get a win as they're the only winless team still in the league lol.
"We hold these truths t-be self-ful evident. All men and women created by the.. Go-you know the.. you know the thing!" - Joe Biden