Some have been more memorable than others, but each appearance has been important to the fans of one of the best sports cities in America.
Never in the history of Chicago sports have all teams done well as simultaneously as they have within the past 10 to 11 years.
Based on talent, with both playoff and regular-season performance taken into consideration, these are the rankings for the best Chicago playoff teams of this century.
Regular Season: 85-77, NL Central Champions
Playoffs: Swept 3-0 in NLDS by the Arizona Diamondbacks
In Lou Piniella's first year with the Cubs, the team improved by 19 games and came out of nowhere to win the National League Central.
Alfonso Soriano looked like he was worth the money the Cubs spent in the offseason to acquire him. The starting pitching was on point, and the Cubs got hot at the right moment.
Unfortunately, the Cubs cooled down at the worst possible time, getting swept by the Diamondbacks in three straight games in the divisional series to end the season.
Regular Season: 41-41, Third in Central
Playoffs: Lost to the Cleveland Cavaliers 4-1 in First Round
Had it not been for a late-season Toronto collapse, the Bulls might have watched the playoffs from home.
Instead, they squeaked into the playoffs as the No. 8 seed, losing to the LeBron James-led Cavaliers in five games.
The 2010 playoffs marked a turning point for both Cleveland and Chicago, as the teams would go in very different directions the following year.
Regular Season: 96 Points, Third in Central
Playoffs: Lost to the St. Louis Blues 4-1 in First Round
The 2001-02 Blackhawks played consistently well in the regular season, earning them a No. 5 seed in the playoffs, an appearance that would be their first since 1997.
Facing future coach Joel Quenneville of the Blues, the Blackhawks took Game 1, but were shut out in three of the next four games and lost the series in five.
It would be the last time that longtime Chicago greats Tony Amonte and Eric Daze would make a playoff appearance for the Blackhawks.
Regular Season: 95-67, AL Central Champions
Playoffs: Swept 3-0 by the Seattle Mariners in ALDS
Like many of the White Sox teams in recent history, the 2000 squad hit a lot of home runs—216 to be exact.
That sort of one-dimensionality got the top-seeded White Sox swept by a more complete team in the Seattle Mariners.
It was Jerry Manuel's only playoff appearance in a mediocre managerial tenure with the club.
Regular Season: 13-3, NFC Central Champions
Playoffs: Lost 33-19 to the Philadelphia Eagles in Divisional Round
The 2001 Bears were like most of their teams in history: great defense and lackluster offense.
Though an exciting team to watch in the regular season with five come-from-behind wins, the Bears fizzled at home in their first playoff game since 1994.
Donovan McNabb tore apart the defense all game.
The next day, the Soldier Field grass was torn apart, as the stadium began reconstruction.
Regular Season: 11-5, NFC North Champions
Playoffs: Lost 29-21 to the Carolina Panthers in Divisional Round
After starting 1-3 with a rookie QB in Kyle Orton, the Bears were long shots to make the playoffs. The team then strung together an eight-game winning streak.
On Christmas Day, with Rex Grossman back from injury, the Bears defeated the Packers in Green Bay to win the NFC North title.
The playoffs wouldn't be as kind to the Bears, who saw Panthers WR Steve Smith run circles around the secondary, while future Bear Julius Peppers single-handedly dismantled the Bears offense.
Just like in 2001, the Bears would disappoint at home in the playoffs as the No. 2 seed.
Regular Season: 41-41, Third in Central
Playoffs: Lost to the Miami Heat 4-2 in First Round
Though the Bulls had a .500 record in the regular season, the team in the playoffs looked much different.
The Heat and the Bulls played a grueling six-game series, one that eventual NBA champion Miami would win.
Being overmatched by Shaquille O' Neal and Dwyane Wade, the Bulls showed heart and kept up with a team that was way better on paper.
Regular Season: 41-41, Second in Central
Playoffs: Lost to the Boston Celtics 4-3 in First Round
For much of the 2008-09 season the Bulls were an inconsistent bunch. Derrick Rose won Rookie of the Year and was great all season, but if it weren't for a late-season push, the Bulls wouldn't have made the postseason.
The Bulls and Celtics played the best playoff series of all time in the first round of the 2009 playoffs. A seven-game series saw four of the games go into overtime with seven overtime periods altogether.
Boston, who were the defending NBA champions, leveled the playing field without having superstar Kevin Garnett in the lineup, but the Celtics still won 21 more games in the regular season than the Bulls did.
The Bulls lost in seven, but Joakim Noah and Derrick Rose showed that the team would be a force to reckon with for years to come.
Regular Season: 89-74, AL Central Champions
Playoffs: Lost 3-1 to the Tampa Bay Rays in ALDS
The 2008 Chicago White Sox had no business being in the playoffs. It took three games in three days against three different teams to get there.
After winning the last scheduled game of the season against the Indians and a makeup game against Detroit, the White Sox forced a one-game playoff against the Minnesota Twins. Chicago would win 1-0 on a Jim Thome homer to give them their first division title since 2005.
Once in the playoffs, however, the eventual American League champion Rays took care of business, with the White Sox only winning Game 3 of the series.
Regular Season: 47-35, Second in Central
Playoffs: Lost to the Washington Wizards 4-2 in First Round
The 2004-05 season marked a resurgence for the Chicago Bulls franchise. It was the first time since the Jordan era that the team had a winning record and made the playoffs.
After winning the first two games in the first round against Washington, the Bulls dropped the next four, although they hung tough in every game.
Starting the season 0-9, no one expected the Bulls to make it that far. Overall, the season was a success as it put the Bulls in a playoff position where they would be for the following years.
Regular Season: 97 Points, Third in Central
Playoffs: Lost to the Vancouver Canucks 4-3 in First Round
As the defending Stanley Cup champions, the 2010-11 Chicago Blackhawks had a daunting task ahead of them in repeating. If that wasn't enough, several key contributors to their championship run had departed to make salary cap room.
The Blackhawks struggled through most of the season and made the playoffs as a No. 8 seed.
In the postseason, the 'Hawks squared off against a big-time nemesis in Vancouver. The Canucks won the first three games, and it appeared as if Chicago was dead in the water.
Then, the team woke up. The Blackhawks won the next three games and forced a Game 7 in Vancouver. The eventual Western Conference champion Canucks won in overtime, but with the way things could have turned out, the Blackhawks' season was salvaged.
This team showed that it could compete even when a large portion of their former players had gone to new clubs.
The Blackhawks will continue to be one of hockey's elite in the future.
Regular Season: 97-64, NL Central Champions
Playoffs: Swept 3-0 by the Los Angeles Dodgers in NLDS
Normally, I wouldn't put a team that failed to win a playoff game this high on a list such as this, but the Cubs were so dominant in the regular season.
If there was a Cubs team that had the capability to win the World Series, this was it.
In the regular season, the offense scored in bunches, the starting pitchers went deep into games and the bullpen was solid.
Then came the playoffs.
The Los Angeles Dodgers, led by newly acquired Manny Ramirez, took apart the Cubs pitching and left the team in the dust.
Unfortunately for the Northside faithful, "Wait 'til Next Year" lives on.
Regular Season: 49-33, Third in Central
Playoffs: Lost to the Detroit Pistons 4-2 in Conference Semifinals
By the time the Bulls made the playoffs for the third straight year, the team had vastly matured. After playing a fundamentally sound regular season, Chicago made the playoffs as a No. 5 seed, though they had the third-best record in the Eastern Conference.
In the first round, the Bulls got revenge on the defending champion Miami Heat, who had eliminated them from the playoffs in the previous season. The Bulls swept Miami for their first series win since the 1998 NBA Finals.
The top-seeded Detroit Pistons defeated the Bulls in six games the following round. Detroit's depth and experience was too much for Scott Skiles' bunch to overcome.
The Bulls may not have gotten as far as Chicago would have hoped, but this season showed glimpses of greatness not experienced since MJ left town.
Regular Season: 104 Points, Second in Central
Playoffs: Lost to the Detroit Red Wings 4-1 in Western Conference Finals
After years of underachieving in front of half-empty home crowds, the 2008-09 Blackhawks took the National Hockey League by storm.
It was in this season that "One Goal" was adopted. This season brought the Chicagoans back to the United Center in numbers never seen before.
After a tremendous regular season, the Blackhawks entered the playoffs as the No. 4 seed in the West. The 'Hawks defeated the Calgary Flames in six games in the first round, thanks to the heroics of Martin Havlat and the superb goaltending of Nikolai Khabibulin.
Vancouver was next up for Chicago, beginning the first of three straight playoffs that the teams would meet. The teams went back and forth for the first four games, before the Blackhawks won Games 5 and 6.
Chicago faced Detroit in the Western Conference finals, pitting the arch rivals against each other for a trip to the Stanley Cup Finals. The more-experienced defending champion Red Wings made quick work of the Blackhawks, eliminating them in five games.
The Blackhawks didn't win the Cup in 2009, but the season may have been one of the most important in team history. Greatness was on its way.
Regular Season: 11-5, NFC North Champions
Playoffs: Lost 21-14 to the Green Bay Packers in NFC Championship
Coming into the 2010 season, there wasn't much expected of the Chicago Bears. The Bears went 7-9 the year before and Jay Cutler threw 26 interceptions.
2010 proved to be much better for the Bears. Cutler improved and newly acquired Julius Peppers anchored a defense that had been porous in previous years.
The Bears won the NFC North and earned the No. 2 seed in the NFC playoffs. Chicago dismantled Seattle 35-24 in the divisional round to set up an NFC championship against a bitter enemy, the Green Bay Packers.
Unfortunately, the Bears' season would end at the hands of Green Bay, who went on to win their fourth Super Bowl.
The Bears head into 2011 with just as many question marks as before, including the desire of QB Jay Cutler.
One thing the 2010 season made clear is that the Bears are capable of winning again.
Regular Season: 88-74, NL Central Champions
Playoffs: Lost 4-3 to the Florida Marlins in NLCS
What more can you say about the 2003 Chicago Cubs?
A hot September gave the Cubs their first playoff appearance since 1998. In the NLDS, the Cubs ousted Atlanta in five games, winning their only postseason series since the 1908 World Series to date.
The Cubs faced off against a surging Marlins team in the NLCS, and we all know how that turned out. After squandering a 3-1 series lead, the Cubs lost in Game 7 to the Marlins, who would go on to win their second World Series title.
Everyone has their qualms with the Steve Bartman incident, but when it came down to it, errors on the field did the Lovable Losers in.
This season was a monumental moment in Cubs history. It's the closest the Cubs have come to glory in a long, long time.
Should the Cubs get this far again in the future, they can look back on this season as a guide for what to do and not do in search of that elusive World Series title.
Regular Season: 62-20, Central Division Champions
Playoffs: Lost to the Miami Heat 4-1 in Eastern Conference Finals
This was the season that Bulls fans had long been hoping for. Derrick Rose took Chicago from good to great, something the Bulls haven't been since Michael and Scottie were running the floor.
The Bulls stormed through the regular season, winning over 60 games for the first time since 1998. Derrick Rose took the next step in his journey to NBA stardom and won MVP.
In the playoffs, Chicago took care of a scrappy Indiana Pacers squad in five games during the first round.
The Bulls faced off against Atlanta in the conference semifinals, and though the Hawks gave Chicago a scare at times, Rose, Noah and Co. were too much. The Bulls won in six.
The Eastern Conference finals pitted the Bulls against LeBron James, Dwyane Wade and the Miami Heat. The Bulls took Game 1, but the talent and experience on the Heat roster was too much for first-year coach Tom Thibodeau's team to overcome. Miami took it in five.
No, the Bulls didn't win their seventh championship, but this season was huge. The Bulls are great again. If the core of Rose, Noah and Boozer continues to improve, expect there to be more banners hanging from the rafters of the United Center.
Regular Season: 13-3, NFC North Champions
Playoffs: Lost 29-17 to the Indianapolis Colts in Super Bowl XLI
Like much of the Bears teams in the past, defense was the name of the game for the Chicago Bears. A stellar defense matched with rookie Devin Hester's magnificence in the return game propelled to the Bears to their first Super Bowl appearance since 1985.
The Bears came off a division title in 2005, and were looking to improve. They did, but it wasn't easy the entire way. Rex Grossman came down to earth after a great start and became the inconsistent QB that would define his career as a Chicago Bear.
Chicago would defeat Seattle in the divisional round thanks to a game-winning field goal by Robbie Gould in overtime.
In the NFC Championship Game, "Bear weather" took over and Chicago stormed past the New Orleans Saints, 39-14.
The Super Bowl would be a different story. It came with a promising start as Devin Hester returned the opening kickoff 92 yards for a touchdown, but the bad Rex Grossman showed up. Peyton Manning and the Colts went on to win their first Super Bowl since moving to Indianapolis.
The Bears were close to their second Super Bowl title, but it just wasn't in the cards for Lovie Smith's team.
With the Bears coming off a season in which they were one win away from reaching the Super Bowl, there is promise.
As for those Bears fans born after the 1980s such as myself, this is the greatest Bears team we have seen to date.
Regular Season: 112 Points, Central Division Champions
Playoffs: Won the Stanley Cup 4-2 against the Philadelphia Flyers
After 49 years of frustration, the wait was over. The Chicago Blackhawks were the Stanley Cup champions once again.
The 2009-10 season will be a time that Blackhawks fans reminisce about for years to come.
The 'Hawks stormed through the regular season, earning the No. 2 seed in the Western Conference. Nashville fell victim to the Blackhawks first in the opening round, losing to Chicago in six games.
The Blackhawks faced familiar foes in Vancouver in the second round, and defeated them in six games for the second year in a row.
San Jose, the No. 1 seed, was perhaps the easiest test the Blackhawks faced all year long, as Chicago swept them in four.
Philadelphia was the lone team standing in the Blackhawks' way of the Cup. Their team of enforcers nearly pushed the 'Hawks to the brink, but Patrick Kane's overtime goal in Game 6 ended it.
The Blackhawks had captured the Stanley Cup.
No one in Chicago could have predicted this moment years before it happened. Just years after being named America's worst sports franchise by ESPN, the Blackhawks had completely turned around.
The team had the city's heart again, and it looks like they're here to stay.
Regular Season: 99-63, AL Central Champions
Playoffs: Won the World Series 4-0 against the Houston Astros
After 88 years of futility, the Chicago White Sox won the World Series in 2005.
The reason this team tops this list is the way in which they did it. They completely dominated the regular season, earning the top seed in the American League.
In the playoffs, the White Sox completely dismantled the defending champions, the Boston Red Sox, sweeping them in three straight games, including a 14-2 rout in Game 1.
After losing Game 1 to the Los Angeles Angels of Anaheim in the ALCS, the White Sox won the next four, capturing their first American League title since 1959. Games 2 through 5 featured four straight complete games by Mark Buehrle, Jon Garland, Freddy Garcia and Jose Contreras, a rare feat, especially for modern-day baseball.
The White Sox went on to sweep the Houston Astros in the World Series. All four games were close, but it was the pitching and timely hitting that made this team great, and ultimately delivered the title to the Southsiders.
In Chicago, the White Sox may not be the most popular team, especially when it comes to baseball. However, their domination in 2005 makes them the greatest Chicago sports team so far in the 21st century.