NORTH SIDE BEARS: On the street outside Wrigley Field.
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Wrigley Field, Chicago

As the late, great broadcaster Harry Caray used to gush into his microphone at Wrigley Field, “Aah, you can’t beat fun at the old ballpark!”

Good thing that has held true for Chicago Cubs fans over the years because the home team hasn’t won a championship since before 1916, when it moved into Wrigley Field on the North Side of the city.

The early Cubs did win the World Series in 1907 and 1908, back when they played at West Side Park, which means that their official championship drought is going on 105 years. But, hey, anybody can have a bad century. (My smirking disclaimer: As a native Chicagoan who occasionally skipped college classes to sit in Wrigley’s right-field bleachers and watch the Cubs lose, you sometimes have to joke about your misery to keep your sanity.)

To be fair, the Cubs have had several near misses at Wrigley through the years, losing five World Series between 1929 and 1945. In the 1932 Series, Yankees slugger Babe Ruth famously rubbed it in by pointing toward center field before hitting a tie-breaking homer in Game 3. The Cubs also blew a two-game lead in the best-of-five 1984 National League Championship Series against the San Diego Padres and were five outs from reaching the 2003 World Series until now-notorious Cubs fan Steve Bartman interfered with a catchable foul ball that provided the impetus for an epic collapse against the Florida (now Miami) Marlins.

Slugger's Sports Bar
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Even so, Cubs fans keep coming back for more at the “Friendly Confines,” the second-oldest ballpark in the majors, which is built on the site of a former seminary. Now you know why watching the Cubs is a religious experience for many. Each visit to this national treasure of a ballpark is like entering a museum, if not a time warp, with its red marquee out front; its tiny wooden seats and outfield bleachers; its ivy-covered brick outfield walls; its original, hand-operated scoreboard; old-time organ music coming from the sound system; and fans in the streets with gloves, waiting for batting-practice home runs to fly out of the ballpark. Nearby, the elevated trains rumble past.

The ballpark is tucked neatly in a residential neighborhood known as Wrigleyville and is surrounded by souvenir shops as well as restaurants and bars where fans congregate. Of the dozens of establishments in the immediate vicinity to eat, drink and hang out, the most popular are Murphy’s Bleachers, Sluggers World Class Sports Bar & Grill, and The Cubby Bear. Murphy’s Bleachers (formerly Ray’s Bleachers, during my college days) sits directly across from Wrigley. It’s where Wrigley’s “Bleacher Bums” became famous during the 1969 pennant race and where celebs such as Bill Murray sometimes show up. It features inside and outside dining, several big-screen TVs, plenty of beer choices, a bloody-mary bar, lots of Cubs memorabilia and a beer-pong table in the basement.

Sluggers, once ranked among baseball’s top 10 sports bars by ESPN, has been described as “a sports bar on steroids.” It features a handful of 12-foot big screens among its 30 TV monitors, dueling pianos, a dance floor and an extensive beer and food menu. What separates it from its competitors is a second-floor indoor sports complex featuring batting cages — yes, full cages with pitching machines — as well as assorted electronic games. The Cubby Bear, across the street from Wrigley’s marquee, is a 30,000-square-foot venue with 75 plasma TVs and is known for its live music.

If you don’t have a ticket to a game, or if you want to watch from a different vantage point or with a large group of friends, there are 16 buildings across the street from the ballpark with rooftop access, all of which offer food, booze and long-distance playing-field views for one price. But you have to buy a special ticket or book a private party to enjoy the rooftop experiences.