Generous Tipping Experiment

The valet had a big grin on his face as he looked me in the eyes and said, “thank you” in broken English as I slipped him $5 in front of the Intercontinental Hotel in Chicago.  I guess most people don’t tip the valet when they check their car in.  I know I usually do it when I pick it up.  But my wife and I were in the Windy City for a romantic weekend and we had plenty of cash to tip generously. 

It was a great weekend.  Some of our tips while here included:

• $50 for a $100 meal
• Numerous other 30% + tips on various meals (we love to eat in the city)
• Many, many $5 to $10 tips on small taxi fares
• Too many tips for valets and doorman to count

You know that generosity is rare in the city when a taxi drive tells you the tip is too much and tries to give you some of it back!  That happened to my wife when she was taking a cab from her conference back to our hotel. 

 I think generous tipping brings a new level of excitement to a weekend in the city because there are opportunities to do it often and largely.