The Chicago Bulls are heading into 2026-27 with expectations that aren’t especially high in the win-loss column, but that doesn’t mean the schedule is short on intrigue. A full front office overhaul and a new head coach have pushed the organization into a rebuild, and the next phase is supposed to be built around Caleb Wilson, the No. 4 overall pick the Bulls landed with a little lottery luck.
Wilson won’t be alone in giving this season some juice. Dailyn Swain, Matas Buzelis, Josh Giddey, recent All-Star Norman Powell and rim protector Nic Claxton all give Chicago a mix that should be worth watching, even if the results are uneven. And with the 82-game slate now out, there are still plenty of dates that stand out.
One thing to note right away: only 80 games are currently on the books because of the NBA Cup. If the Bulls don’t advance, two more games will be added in mid-December.
The opener against Toronto sits at the top for obvious reasons. It’s the first chance for Bulls fans to see this young group together, and it also drops them right into a difficult test.
The Raptors are expected to move up the East standings, and there’s even the possibility that Kawhi Leonard’s first game back in Toronto comes in that one, if the trade with the Clippers is finalized before opening night. That would make the debut even rougher for Chicago.
The matchup itself also has a certain stylistic edge, since the Bulls look built in a similar mold to recent Raptors teams: long wings, toughness, and an emphasis on attacking the rim. That has the makings of a physical start.
The home opener against Washington is another obvious circle-on-the-calendar game, and it comes just four days into the season. It will be Wilson’s first look at the United Center crowd, and the opponent could be a much more interesting Wizards group than in recent years.
Trae Young and Anthony Davis are part of a young nucleus that is trying to change Washington’s fortunes, and the game also sets up Wilson’s first head-to-head with No. 1 overall pick AJ Dybantsa. The two were supposed to meet in Las Vegas before the Wizards shut Dybantsa down early, something Wilson apparently enjoyed.
Chicago will also be on the second night of a back-to-back, after playing in Milwaukee the night before.
A trip to New York also jumps off the page. The Bulls will already have seen the Knicks once by the time this game arrives at Madison Square Garden, but this one feels bigger.
Playing the defending champs on their home floor is tough enough. Doing it as one of the youngest teams in the league, at Madison Freakin' Square Freakin' Garden, makes it even more daunting.
Another marquee road stop comes a week earlier in Philadelphia. The Bulls will have already visited the 76ers by the time this one rolls around, but the United Center setting gives it extra weight.
LeBron James and Jaylen Brown are coming to Chicago, and that alone makes it a can’t-miss night. The atmosphere should be strong, and Caleb Wilson will have a chance to put on a show in front of the home crowd.
Chicago’s first national television game is another major checkpoint, and it comes against the Knicks at the United Center. It will also be the Bulls’ first game on NBC since the network’s partnership with the NBA returned last season. The Bulls showed up on Peacock a couple of times in 2025-26, but this is a different stage entirely, with the kind of broadcast that is sure to bring out the Michael Jordan flashbacks.
Then there’s the Lauri Markkanen game at the United Center, which has its own obvious appeal. The rivalry flavor is there, and Darryn Peterson adds another layer since he was one of the Top 2 picks Wilson didn’t get to face in Summer League.
Peterson has made it clear he wants to prove he’s the best player in the draft class, and this is another chance to do it in front of his home crowd. Powell also has a little extra reason to care here after the Bulls let him walk this summer, even if he’s now settled in with Chicago’s rebuild.
The Bulls’ first mini-series of the season comes against Miami, where they’ll face the Heat twice on the road in three days. That should turn into a real coaching chess match, with Tiago Splitter taking on Erik Spoelstra. Those games are always worth watching for the sideline duel alone.
Minnesota’s visit to the United Center also belongs on the list. The Anthony Edwards and LaMelo Ball pairing is still a question mark, but it should create a lively building.
Chicago’s backcourt defense is going to be tested, and the bigger tactical question is how the Bulls handle the absence of both Naz Reid and Julius Randle. It will also be Ayo Dosunmu’s first game back at the United Center, which should come with a tribute video.
The calendar also hands Chicago a Valentine’s Day trip to Portland, and that one carries a few different hooks. It’s a Super Bowl appetizer, it comes with a head coach revenge angle, and it will be Tiago Splitter’s first return to Portland after the organization failed to lock him down as its next head coach. He may keep things polite, but the source of that split clearly still matters.
Finally, the Bulls’ meeting with Cleveland stands out because of the matchup between Wilson and Cameron Boozer. The two already gave fans a memorable one in Las Vegas, when Wilson hit seven three-pointers and scored 35 points, only for Boozer to answer with a strong all-around performance and a one-point win. Their games are different enough to make every meeting feel fresh, and that alone makes this one worth the wait.
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