Five Things for Guys to Do In Chicago

by Sean Heffernan

The Windy City is one of greatest places in the world to be a guy. A sports fan could find a professional sports event almost every night of the year to attend. There are more sports bars and Irish pubs than any single drunk’s liver could handle in a lifetime. The city is world famous for two of the greatest guy foods in history: Pizza and hot dogs. What else could you want in a city? Here’s my list of five things for a guy to do in Chicago, IL...

1.      Enjoy the Best Baseball Town in

 

 

 

 

 

 

 

 

 The dislike between Chicago Cubs and White Sox fans is legendary and as fierce as any intercity rivalry in the country. I have a friend that will in the middle of any conversation burst into a “Cubs Suck” tirade without any apparent warning.

The Cubs’ Wrigley Field is one of the most hallowed sports venues in America. There’s truly nothing like watching the Cubs stumble all over the diamond and run into the ivy while sitting in the bleachers drinking a cold Old Style. Outside of the game awaiting you is block after block of bars and restaurants. Whether you’re looking for a sports bar, dance club, hole-in-the-wall, or reggae joint you’ll have a good, dirty time in Wrigleyville.

On the Southside of town the White Sox have bragging rights after bringing home the World Series in 2005 (a feat the more popular Cubs haven’t done in 100 years…literally). The neighborhood might not be as trendy around the Sox’s U.S. Cellular Field as Wrigleyville, but the food inside the stadium puts Wrigley’s cuisine to shame. “The Cell” as its nicknamed has all the modern amenities Wrigley lacks as it was built in 1991 and since U.S. Cellular bought the rights in 2003 the stadium has been renovated regularly. After the game I suggest you hit up Schaller’s Pump for the bar’s legendary butt steak. It’ll kick your ass.

No matter if you’re a pompous yuppie of a Cubs fan, a classless degenerate of a Sox’s fan, or just a guy looking for a good time at the ballpark than you’ll fit right in Chicago.

2.      Viva Football/Futbol

 

It should tell you something that the most famous person in Chicago is Mike Ditka the mustached and pompadoured football coach who led the 1985 Bears to the organization’s one and only Super Bowl victory. “Da Coach” eventually fell out of favor after ‘85 and was fired, but no one remembers that. In the fall the city comes together to support Da Bears. As it gets cold later on in the season tailgaters’ polish sausage and Italian beef will keep you warm outside Solider Field. The Bears are on the front page of the Tribune and the Sun Times regardless of their record. Soldier Field may look like a weird spaceship from the outside, but inside it is a great place to watch a sporting event.  

Bears tickets will put a nice dent in your wallet so if you’re looking for a good time at a discount I suggest you opt for the other type of football that is played south of the city at Toyota Park. The new stadium is home to the MLS’s Chicago Fire as well as summer concerts, and the occasional national team game. I recently attended a Chicago Fire playoff game and sat in the Miller Lite deck. For the price of admission you get four beers and all you can eat concessions until the 20^th minute of the game. Needless to say I was a happy guy before half time with my pockets full of hot dogs and condiments. A Fire game is definitely one of the best bangs for your buck in the city. .

3.      Go Watch the Ponies Run at Arlington

Northwest of the city your fortunes await you at Arlington Park where you can spend the entire day losing/winning money on horse racing, eating crab cakes, listening to live music, and blowing as much or as little cash as you want at the historic race track. You’re welcome at Arlington whether you’re a high roller or just a guy willing to part with a few bucks. You can dine on shrimp cocktail and filet mignon in the Million Room or eat a cheeseburger and corn on the cob outdoors at The Park.  People look forward to The Arlington Million all year in August when a million clams is on the line for some midget on a horse to win. It’s a good time.   

4.      Eat Something Bad For You

Chicago isn’t famous for its salads, but if you’re looking for great guy food and willing take a few years off your life than you can’t find a much better place than the Windy City. Chicago’s deep dish pizza is world famous with the likes of Gino’s East, Giordano’s, and Lou Malnati’s battling it out to be the best pizza place in Chicago.

When it comes to hot dogs you’d be hard pressed to walk down the street in most parts of Chicago and not run into a place that serves Vienna Beef wieners on a poppy seed bun with relish, mustard, tomato slices, dill pickle, sport peppers, celery salt, onion, and cucumber smothered with cheese of course upon your request.

The Chicago style dog came about in the Great Depression when hot dog had to be your entire meal. Just don’t let any mustached Chicagoan catch you putting ketchup on your dog or you’ll get an earful. The general rule is for Chicago hot dog eating is that the dirtier looking the place the better the dog, but a few of the more popular places include Portillo’s, Superdawg, Gold Coast Dog’s, and Hot Doug’s. 

Italian beef is another Chicago delicacy that no man should pass up in their lifetime. Hot beef on a warm bun dipped in Au Jus has probably killed more Chicago males than cancer in the last century. Al’s Beef and Buona Beef have taken the tradition into the mainstream, but they’re plenty of original places for a beef lover to sample all over the city.   

If you want to avoid a heart attack or you’re a bit more of a classy individual the city has some of the best restaurant in the country in every category imaginable, but personally I believe the city’s true soul is in its working class guy grub. Here’s to antacids! I think I just gained four pounds writing this article.

 

5.      Laugh Until You Puke

For 50 years Chicago’s The Second City Theater has been at the forefront of improvised comedy. Since the theater’s opening in Chicago’s Old Town neighborhood in 1959 the company has expanded to Toronto and Hollywood. The theater’s famous alumni include John Belushi, Bill Murray, Chris Farley, Steve Carell, and Tina Feys. I went to see a show for my brother’s bachelor party and it was hysterical. A few months later I saw one of the actors on T.V.

Feature shows are always playing at Second City and training classes are available if you think you got what it takes to make people giggle. In the spirit of Second City a number of other improv troupes perform all over the city including the Improv Olympic and ComedySportz.

Chicago continues to be the leading city in American comedy so when you see a show you never know if you are watching the next SNL cast member or comic legend. So after you catch a game and eat entire deep dish pizza go see a show and laugh until you puke.

 

 Do you have any thoughts about what's a good time in the Windy City? Please comment below!