The two cities hadn't met in the MLB playoffs since the Yankees swept the Cubs in the 1938 World Series. But Chicago and New York have collided plenty of times in other sports' postseasons, with Chicago winning 19 of the 29 series or single-game playoffs.
Here's a look at the records and memorable moments from past Chicago-New York postseason meetings in the top four North American leagues. This includes New York City-area teams based in New Jersey.
MLB: New York has won two of three postseason series against Chicago, with all three meetings in the World Series more than 75 years ago. The White Sox beat the Giants in six games in 1917, two years before the infamous Black Sox scandal.
The Yankees swept the Cubs in both 1932 and 1938. Game 3 in 1932 featured one of baseball's most famous moments, Babe Ruth's home run off Charlie Root. Ruth might or might not have called his shot when he pointed at Root before hitting the home run.
NBA: The Bulls have won eight of their nine postseason series against the Knicks and Nets. Chicago went 6-1 against the Knicks between 1981 and 1996, losing only in the 1994 conference semifinals. Michael Jordan was temporarily retired during that series, and he won all six of his playoff matchups with New York-area teams.
There's no shortage of famous playoff games between the Bulls and Knicks, including:
1991 Eastern Conference first round, Game 3. Jordan spun out of a double team, drove baseline and dunked on Patrick Ewing. "My most memorable dunk, the one that I think about very, very often is the Patrick Ewing dunk," Jordan said. "That's only because Patrick and I are such great friends."
1993 Eastern Conference finals, Game 2. John Starks drove baseline and dunked on Horace Grant and Jordan. It's a play that has been creatively dubbed "The Dunk."
1993 Eastern Conference finals, Game 5. After trailing 2-0 in the series, the Bulls took a commanding 3-2 lead when Knicks forward Charles Smith missed four consecutive layup attempts in the game's final seconds.
1994 Eastern Conference semifinals, Game 3. Scottie Pippen refused to take the court for the final 1.8 seconds after Bulls coach Phil Jackson drew up a play for Pippen to inbound the ball to Toni Kukoc for the potential game-winning shot. Chicago burned a timeout and inserted Pete Myers to inbound the ball. Kukoc would hit the winner and the Bulls triumphed 104-102.
1994 Eastern Conference semifinals, Game 5. In a controversial ending, Pippen was whistled for a foul on Hubert Davis' field goal attempt with 2 seconds remaining. Davis hit both foul shots, and the Knicks won 87-86.
1994 Eastern Conference semifinals, Game 6. Pippen ran down the sideline, grabbed a cross-court pass and elevated over Ewing for the poster dunk. Pippen then shoved Ewing and walked over him to pick up a technical foul.
NHL: Chicago has won five of nine NHL playoff series against New York teams, though the two cities haven't met since 1979 thanks to the Blackhawks switching conferences before the 1981-82 season.
Chicago has never played a New York team in the Stanley Cup finals, but the Blackhawks and Rangers did meet in the semifinals in three consecutive seasons from 1971 to 1973. Perhaps the most memorable moment was Pete Stemkowski's triple-overtime goal in Game 6 in 1971. That tied the series for the Rangers, but the Blackhawks advanced in seven games.
In 1977, the Blackhawks had to play a "home game" at the Islanders' Nassau Coliseum because Led Zeppelin had already booked Chicago Stadium. The Islanders won that game to sweep Chicago 2-0 in the preliminary round.
NFL: The Bears have won five of eight playoff games against the New York Giants, who won the teams' most recent meeting, 31-3 in the 1990 divisional playoffs. All eight times, the winner has won the NFL title, though that's a deceptive stat since six of those clashes were in the NFL Championship Game prior to the Super Bowl era. A notable meeeting was the 1934 NFL title game, known as "The Sneakers Game" because the Giants changed into basketball sneakers at halftime in order to get better footing.
One more recent memorable moment came during the 1985 divisional round. New York's Sean Landeta was punting from his own end zone, into the teeth of a Chicago wind. He nearly missed the ball entirely, and Bears cornerback Shaun Gayle picked it up and returned it for a five-yard touchdown en route to Chicago's 21-0 victory and eventual Super Bowl title.