Have you ever liked a joint so much that you stay across the street from it when in town?  I have, willing to sacrifice a luxurious stay at a fine downtown hotel for an overpriced stay at the Marriott Courtyard, just to be within walking distance of O’Callaghan’s on Hubbard Street.

An Irish green storefront, O’Callaghan’s has a few outdoor tables that can be used on the days in Chicago that aren’t winter.  Entering the small door and walking up the stairs at O’Callaghan’s is quite a challenge.  Not because imbibing has brought on a loss of balance.  Heck, the bar is at the top of the stairs.  It is just that at the bottom of the stairs, at the entrance, rests one of Chicago’s best jukeboxes causing serious tune searching even before wetting your whistle.

The bar is long and narrow with tables at your back.  The great-recorded music resonates off of the brick walls.  A half a dozen TV’s are strategically placed for viewing sports, which in Chicago is a birthright.  A basket of mini-pretzel twists and a small bowl of mustard are the bar snack.

The crowd is typically thirty-something yuppie, with a good balance of men to women.  A wide beer selection exists with about 20 available on tap.  The menu is full of great burgers, melts, salads and a must for the Chicago winters: homemade soup.

I’ve spent many evenings at O’Callaghans lamenting a sports loss: either feeding the horses at Arlington Park, watching ‘da Bears beat my beloved Raiders, or watching the Cubs lose to Cal State Fullerton or Little Sisters of the Poor.   Some how I feel better after a few hours of counseling from the friendly staff.  By the way, O’Callaghan’s stays open until 4 a.m., which explains in part why I stay across the street.

Walking down the stairs is less of a challenge than walking up, especially if your jukebox set is done and you are staying across the street.  Watch out for the revolving door at the Courtyard, however. – D.M.