What to do in Chicago after golf (when real money counts, meaning you actually look at the bills you get and have some kind of budget when on vacation).  Here is the Chicago Golf Guy’s top 5 things to do in Chicago that doesn’t involve golf:

1. Go To Portillos:  If I had one meal left on earth, and I’m talking Death Row, Dead Man walking, I would get my last meal from Portillos.  Everything on the menu is great.  From Hot Dogs (yes they come Chicago style automatically), to Italian Beef, to Cheese Burgers, to the salads, to the pasta, and if you are there on Rib night then you might have just died and gone to heaven.  Portillos is the one restaurant that I would consider eating at every day for the rest of my life.  I do not know what more I can say besides that.  There are locations all over Chicago, so no matter where you are staying you can find a Portillos that is close.  Remember that in Chicago, we do not put Ketchup on our hot dogs. So when you get a Hot Dog, know that Chicago Style is: Neon Green Relish, Onions, a Dill Pickle Slice, Tomato slices, yellow Mustard, on a Poppy Seed bun.  There are no other ways to get a hot dog while in Chicago.  I know that if you ask for Ketchup, we are gonna know your a tourist.
2. Go to a Cubs game: Wrigley Field is quintessential Chicago.  When someone says “hey Im from Chicago” the first thing people ask back is are you a Cubs fan?  The most beloved team in all of baseball, despite their record.  If you are in Chicago, and you are going to spend an afternoon not playing golf, this is the place to be.  Get an Old Style, sit in the bleachers, and drink among the greatest fans of baseball.  If Baseball is America’s past time, then Wrigley Field is Chicago’s most notorious tourist attraction.  Just be careful of any home runs hit by the other team, you are going to have to throw that ball back on the field… like it or not!
3. Check out the Sears Tower:  No matter who owns the Sears Tower it will always be the Sears Tower to me.  For example.  Currently  Willis, owes the Sears Tower.  So if you are outside the building, it says Willis Tower.  Yes as in What cho talking bout Willis, Willis Tower.  Anyways, the Skydeck which is new for us Chicagoian (a few years old, but still really cool).  It is a glass elevator on the observatory deck at the Sears (Willis) Tower. What the heck is a glass elevator?  Well, you walk into a glass box, that is outside the 1300 foot tower with nothing below you but glass.  It is a Vertigo and a half feeling when you step out into this glass box.  Trust me, you will not mind the airport like security by the time you get to see Chicago’s best view from 1300+ feet.
4. Check out the festival of the week:  Depending on the time of year, there is some kind of fest going on in Chicago, no matter what time of year it is.  If it is the Old Town Art Festival, or the Taste of Chicago, or the Gay Pride Parade (it doesn’t matter to me what your into), Chicago’s Jazz Fest,  or the countless other neighborhood festivals that run all summer long.  There is always something going on that will tickle your fancy.  Not to mention that there is great street food, and drinks to be had at every one of Chicago’s very own little street festivals.  I promise that you will have a good time at any of Chicago’s Street Fests.
5. My favorite bars in Chicago: This was a tough one, to find a bar that every one likes is difficult to say the least.  Some like the down and dirty dives, some like the club experience, and others just like a good place to drink with no frills.  Here are my favorite bars to check out while in Chicago:  The Bedford is a new bar in Chicago’s Bucktown/Wicker Park Area, but it is one of my favorites to drink at.  I personally got engaged at the Bedford, and I love the different drinks that they have to offer.  Are you man enough to try a Cucumber Coolie?  Smart Bar.  Smart Bar is one of Chicago’s only 4 am bars, meaning that any night of the week they are open until 4am.  With great techno music and some of the greatest Chicago bands of Chicago hanging out after hours (it is in the basement of the renowned Chicago Music Venue the Metro), this is a place to stop if you are into the music scene.  (more bars to come…)

These are some of my favorite things to do in Chicago, when I cannot play golf.  I hope that you enjoy them, and if you find something that you loved while in Chicago (or if you are a native) please send me an email, and you never  know your thing to do just might end up on my list of things to do in Chicago when on a Golf Vacation!